CAS: 87-52-5; 1-(1H-Indol-3-yl)-N,N-Dimethylmethanamine

该化合物是一种合成除草剂,可有效控制长叶草和草杂草. 其关键优势包括系统吸收,允许有效根对根运输活性成分,以及一系列用于满足各种作物保护需要的应用率.

英文名称1-(1H-Indol-3-yl)-N,N-Dimethylmethanamine
中文名称芦竹碱
IUPAC名称1-(1H-indol-3-yl)-N,N-dimethylmethanamine
其它别名N,N-Dimethyl-1H-indole-3-methanamine; 3-(Dimethylaminomethyl)indole
CAS编号87-52-5
MFCD编号:MFCD00005629
EINECS号:201-749-8
FDA UNII编号:FGQ8A78L14
分子式:C11H14N2
分子量:174.24
产品CID: 1883046
产品分类有机原料→分子砌块→芳杂环类化合物→吲哚类化合物

相似结构搜索
产品信息参考;;;
InChIKey: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3…
计算化学: 氢键受体数1.0氢键供体数1.0可旋转键数2.0

物理性质

熔点131-134°C
沸点293.9°C at 760 mmHg
闪点167°C
密度1.0715 (粗估)
pKa:17.00±0.30(预测)
PSA:19.03
LogP:2.2295
折射率1.5500 (估算)
蒸汽压0.00168 mmHg at 25 °C
溶解性Almost Transparency In Methanol
外观形态米色粉末
储存条件冰箱 (+4°C)
产品应用该品是合成色氨酸的中间体.
性质描述叶片状或针状结晶.熔点138-139°C,溶于醇,醚,氯仿,微溶于冷丙酮,几乎不溶于水和石油醚.

MSDS等安全信息

GHS象形图
GHS符号GHS05;
注释: Corrosion
危险类别皮肤腐蚀类别1B
严重眼损伤类别1
急性毒性类别4(经皮)
急性毒性类别4(经口)
急性毒性类别4(吸入)
水生慢性毒性类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2
警示词Danger(危险)
危险描述H314 |造成严重皮肤灼伤和眼损伤.
H318 |造成严重眼损伤.
H312 |皮肤接触有害.
H302 |吞咽有害.
H332 |吸入有害.
H412 |对水生生物有害并具有长期持续影响.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P264-P270-P280-P302+P352-P330-P362+P364-P501
UN编号NONH for all modes of transport
危险品标志C
安全声明45-36/37/39-26
危险类别码34
WGK Germany3.0

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

indole bis-(dimethylamino)methane N,N-dimethyl(methylene)ammonium chloride formaldehyd3,3'-diindolylmethane α-N-methyltryptophan N-[(1H-indol-3-yl)methyl]benzenesulfonamide ethyl 3-(1H-indol-3-yl)-2-nitropropanoate

合成工艺路线路线简述

合成目标产物 Gramine 主要起始原料 Indole And Formaldehyde And Dimethylamine
120-72-9 = 87-52-5
反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 2 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Basified,Rt
标题:The Structural Simplification Of Lysergic Acid As A Natural Lead For Synthesizing Novel Anti-Alzheimer Agents
作者:Alzweiri,Muhammed; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2021 卷标:47]

120-72-9 = 87-52-5
反应条件:1.1 Catalysts: Zinc Chloride Solvents: Ethanol; 90 Min,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Ph 7,Rt
标题:Efficient And Practical Synthesis Of Mannich Bases Related To Gramine Mediated By Zinc Chloride
作者:Dai,Hong-Guang; Et Al
参考文献:Synthetic Communications 日期:2006 卷标:36(13) 页码:1829-1835]

120-72-9 + 51-80-9 = 87-52-5
反应条件:1.1 Reagents: Sulfur Dioxide Solvents: Acetonitrile
标题:The Activation Of Aminals And Aminol Ethers By Sulfur Dioxide And Their Reactions With Electron Rich Aromatic Compounds
作者:Heaney,Harry; Et Al
参考文献:Tetrahedron 日期:1997 卷标:53(39) 页码:13361-13372]

143703-39-3 = 87-52-5
反应条件:1.1 Solvents: Water
标题:A Facile Synthesis Of 3-Substituted Indoles
作者:Nagarathnam,Dhanapalan
参考文献:Journal Of Heterocyclic Chemistry 日期:1992 卷标:29(4) 页码:953-8]

487-89-8 = 87-52-5
反应条件:1.1 Solvents: Ethanol,Acetonitrile; 2 H,Rt1.2 Reagents: Sodium Borohydride Solvents: Ethanol; Rt; 24 H,Rt
标题:Synthesis And In Vitro Evaluation Of Novel 5-Nitroindole Derivatives As C-Myc G-Quadruplex Binders With Anticancer Activity
作者:Nimbarte,Vijaykumar D.; Et Al
参考文献:Chemmedchem 日期:2021 卷标:16(10) 页码:1667-1679]

23543-66-0 = 87-52-5 [标题:Reaction Conditions
标题:Halogenation Of 1-Substituted Skatoles. Preparation Of 3-Bromomethylindoles
作者:Hino,Tohru; Et Al
参考文献:Chemical & Pharmaceutical Bulletin 日期:1975 卷标:23(11) 页码:2990-7]

271-26-1 = 87-52-5
反应条件:1.1 Solvents: Acetic Acid,1,4-Dioxane,Water; 5 Min,0 °C1.2 Solvents: Water; 0 °C; 2 H,0 °C; 0 °C -> Rt1.3 Reagents: Sodium Hydroxide Solvents: Water
标题:Visible-Light-Induced Cascade Dearomatization Cyclization Between Alkynes And Indole-Derived Bromides: A Facile Strategy To Synthesize Spiroindolenines
作者:Gao,Xiaoshuang; Et Al
参考文献:Chemical Communications (Cambridge 日期:2020 卷标:56(90) 页码:14047-14050]

116482-39-4 = 87-52-5 [标题:Reaction Conditions
标题:Product Class 13: Indole And Its Derivatives
作者:Joule,J. A.
参考文献:Science Of Synthesis 日期:2001 卷标:10 页码:361-652]

120-72-9 + 5129-78-2 = 87-52-5
反应条件:1.1 Solvents: 1,1,1,3,3,3-Hexafluoro-2-Propanol; 72 H,40 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; Rt; 2 H,70 °C2.2 Reagents: Water; Cooled
标题:Novel Preparation Of Hemiaminal Derivatives With Bpo And N,N-Dimethylamides And Their Synthetic Use For (Aminomethyl)Indoles
作者:Nakamura,Kohei; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2020 卷标:2020(30) 页码:4713-4722]

120-72-9 = 87-52-5
反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 20 Min,35 °C1.2 Reagents: Sodium Hydroxide Solvents: Water; Ph 11 - 13
标题:Improved Synthesis Of 3-(Dialkylaminomethyl)-Indole In Acetic Acid Aqueous Solution Under Ultrasound Irradiation
作者:Li,Ji-Tai; Et Al
参考文献:Ultrasonics Sonochemistry 日期:2010 卷标:18(1) 页码:42-44]

120-72-9 + 51-80-9 = 87-52-5
反应条件:1.1 Reagents: Sulfur Dioxide Solvents: Acetonitrile; 4 D
标题:Sulfur Dioxide
作者:Burke,Steven D.
参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001 卷标:1 页码:1-6]

120-72-9 + 51-80-9 = 87-52-5
反应条件:1.1 Reagents: Sulfur Dioxide
标题:Bis(Dimethylamino)Methane
作者:Duplantier,Allen J.
参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2001 卷标:1 页码:1-2]

1373493-85-6 = 87-52-5
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; Rt; 2 H,70 °C1.2 Reagents: Water; Cooled
标题:Novel Preparation Of Hemiaminal Derivatives With Bpo And N,N-Dimethylamides And Their Synthetic Use For (Aminomethyl)Indoles
作者:Nakamura,Kohei; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2020 卷标:2020(30) 页码:4713-4722]

64258-88-4 = 87-52-5
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium; 4 H,3 Bar,Rt
标题:The Structural Simplification Of Lysergic Acid As A Natural Lead For Synthesizing Novel Anti-Alzheimer Agents
作者:Alzweiri,Muhammed; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2021 卷标:47]

65283-32-1 = 87-52-5
反应条件:1.1 Reagents: Sodium Borohydride
标题:Reaction Of Nitro Compounds With Immonium Salts. 1. Nitrovinylation Of Indoles
作者:Babievskii,K. K.; Et Al
参考文献:Izvestiya Akademii Nauk Sssr 日期:1977 卷标:(10) 页码:2310-13]

27409-13-8 = 87-52-5
反应条件:1.1 Reagents: Butyllithium Solvents: Toluene,Hexane; 10 Min,0 - 5 °C; 15 Min,0 - 5 °C1.2 Reagents: Diisobutylaluminum Hydride Solvents: Toluene; 5 Min,0 - 5 °C; Rt; 16 H,50 °C1.3 Reagents: Methanol; 10 Min,Rt
标题:A Practical Synthesis Of Indole-Based Heterocycles Using An Amidoaluminum-Mediated Strategy
作者:Todd,Robert; Et Al
参考文献:Synthesis 日期:2009 卷标:(11) 页码:1846-1850]

17206-03-0 = 87-52-5
反应条件:1.1 Solvents: Dimethylformamide; 2 H,160 °C
标题:Synthesis Of N-1-Skatyl Uracil Derivatives
作者:Chernikova,I. B.; Et Al
参考文献:Chemistry Of Natural Compounds 日期:2017 卷标:53(2) 页码:333-337]

496-15-1 + 14002-21-2 = 87-52-5
反应条件:1.1 Reagents: Potassium Tert-Butoxide Catalysts: (Oc-6-42)-[2-[bis(1-Methylethyl)Phosphino-Kp]-N-[2-[bis(1-Methylethyl)Phosphino-... Solvents: Toluene; 36 H,140 °C
标题:Divergence In Ch Alkylation Of Indoles Under Mn Catalysis
作者:Mondal,Akash; Et Al
参考文献:Catalysis Science & Technology 日期:2023 卷标:13(19) 页码:5745-5756]

120-72-9 + 33797-51-2 = 87-52-5
反应条件:1.1 Solvents: Dichloromethane; Overnight,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water
标题:Discovery Of Potent,Selective,Orally Active,Nonpeptide Inhibitors Of Human Mast Cell Chymase
作者:Greco,Michael N.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2007 卷标:50(8) 页码:1727-1730]

120-72-9 = 87-52-5
反应条件:1.1 Reagents: Phosphorus Oxychloride; 0 °C; 1 H,Rt1.2 1 H,Rt2.1 Solvents: Ethanol,Acetonitrile; 2 H,Rt2.2 Reagents: Sodium Borohydride Solvents: Ethanol; Rt; 24 H,Rt
标题:Synthesis And In Vitro Evaluation Of Novel 5-Nitroindole Derivatives As C-Myc G-Quadruplex Binders With Anticancer Activity
作者:Nimbarte,Vijaykumar D.; Et Al
参考文献:Chemmedchem 日期:2021 卷标:16(10) 页码:1667-1679]

120-72-9 = 87-52-5
反应条件:1.1 Solvents: Dimethylformamide2.1 Reagents: Sodium Borohydride
标题:Reaction Of Nitro Compounds With Immonium Salts. 1. Nitrovinylation Of Indoles
作者:Babievskii,K. K.; Et Al
参考文献:Izvestiya Akademii Nauk Sssr 日期:1977 卷标:(10) 页码:2310-13]

52488-36-5 = 87-52-5
反应条件:1.1 Reagents: Acetic Acid Solvents: Acetonitrile,Water; 2 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Basified,Rt2.1 Reagents: Hydrogen Catalysts: Palladium; 4 H,3 Bar,Rt
标题:The Structural Simplification Of Lysergic Acid As A Natural Lead For Synthesizing Novel Anti-Alzheimer Agents
作者:Alzweiri,Muhammed; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2021 卷标:47

3-(N-Formyl,N-Methylamino)Methylindole置于lithium Aluminium Tetrahydride体系中,用四氢呋喃作为反应溶剂,化学反应 2.0H,以95%的收率获得产物芦竹碱
参考文献:用bpo和n,N-二甲基酰胺制备hemiaminal衍生物的新方法及其在(氨甲基)吲哚中的合成用途
标题:用bpo和n,N-二甲基酰胺制备hemiaminal衍生物的新方法及其在(氨甲基)吲哚中的合成用途
摘要:通过在辐射或加热条件下bpo与n,N-二甲基酰胺的反应,可以以高收率获得hemiaminal衍生物.通过使用血红素衍生物,可以通过弗瑞德-克来福特烷基化反应还原带有(n-酰基,N-甲基氨基)甲基的吲哚,从而平稳地获得带有(n-烷基,N-甲基氨基)甲基的吲哚.吲哚和半胱氨酸衍生物.
DOI:10.1002/ejoc.202000680

海关参考信息

2902200000-苯
2921199090-其他无环单胺
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-8063062-B2
优先权日:2006-12-20
标题 :Compounds with a combination of cannabinoid-CB1 antagonism and acetylcholinesterase inhibition
发明人：LANGE JOSEPHUS H M; KRUSE CORNELIS G; SHADID BELAL
权利人:LANGE JOSEPHUS H M; KRUSE CORNELIS G; SHADID BELAL; SOLVAY PHARM BV
摘要:Embodiments of this invention relate to compounds having a combination of cannabinoid-CB 1 antagonism and cholinesterase inhibition, to pharmaceutical compositions comprising these compounds, to methods for preparing these compounds, methods for preparing novel intermediates useful for the synthesis of these compounds, and methods for preparing compositions comprising these compounds. The invention also relates to methods of treating Alzheimer's disease, cognitive disorders, memory disorders, dementia, attention deficit disorder, traumatic brain injury, drug dependence, addiction or substance abuse by administering a pharmaceutical composition comprising these compounds to a patient in need thereof. A compound with a combination of cannabinoid-CB 1 antagonism and cholinesterase inhibition is a compound of formula (1) n nwherein the symbols have the meanings given in the specification.

专利号:US-3627782-A
优先权日:1969-06-12
标题:Synthesis of gramine salt of nitroacetate esters
发明人：LARGMAN THEODORE
权利人:ALLIED CHEM
摘要:Tryptophan, an essential amino acid, is prepared from gramine and an ester of nitroacetic acid by combining gramine and the ester in an inert solvent maintained at about room temperature to form the corresponding salt, and then heating the salt in solution to convert it to the corresponding ester of Alpha nitro- Beta - (3-indole) propionic acid, which is reduced and hydrolyzed in accordance with conventional methods to afford tryptophan. The salt is a novel compound.

专利号:WO-9612402-A1
优先权日:1994-10-19
标题:Herbicide-resistant rice and method of breeding the same
发明人：SHIGEMATSU YOSHIO; OGAWA MASAMI; NAKATA NORIKO
权利人:SANKYO CO; SHIGEMATSU YOSHIO; OGAWA MASAMI; NAKATA NORIKO
摘要:A rice and its seed resistant to a herbicide having a fatty acid synthesis inhibitor activity; a method of breeding a rice and its seed resistant to a herbicide having a fatty acid synthesis inhibitor activity which comprises culturing rice cells in a medium containing the herbicide, selecting cultured rice cells resistant to the herbicice, and redifferentiating the same; a method of breeding a rice seed resistant to a herbicide having a fatty acid synthesis inhibitor activity which comprises culturing the rice seed and mating the same with a rice of another variety; and a method of controlling gramineous weeds which comprises applying a herbicide having a fatty acid synthesis inhibitor activity to the field wherein a rice resistant to the herbicide is cultured. Since the invented rice is resistant to a herbicice having a fatty acid synthesis inhibitor activity, it does not suffer chemical injury due to such a herbicide and gramineous weeds can selectively be controlled.

专利号:TW-I655905-B
优先权日:2012-07-24
标题 :Contains 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof and very long chain fatty acid (VLCFA) Synthesis of herbicidal compositions with fatty acid/fat synthesis inhibiting herbicides

专利号:US-2007099915-A1
优先权日:2005-10-07
标题 :Inhibitors of the hiv integrase enzyme
发明人：DRESS KLAUS R; JOHNSON TED W; PLEWE MICHAEL B; TANIS STEVEN P; ZHU HUICHUN
权利人:PFIZER
摘要:The present invention is directed to compounds of formula (I), n nand pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus (â€œHIVâ€?) integrase enzyme.

专利号:EP-1873155-A1
优先权日:2004-04-26
标题:Inhibitors of the HIV integrase enzyme
发明人：DRESS KLAUS RUPRECHT; HU QIYUE; JOHNSON TED WILLIAM; PLEWE MICHAEL BRUNO; TANIS STEVEN PAUL; ZHU HUICHUN; ZHANG JUNHU
权利人:PFIZER
摘要:The present invention is directed to compounds of formula (I),n nand pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as modulators or inhibitors of the human immunodeficiency virus ('HIV') integrase enzyme.

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