CAS: 130931-83-8; (1S,4R)-2-Azabicyclo[2.2.1]Hept-5-En-3-One

该化合物是一个手性双环长球,结构僵硬,无胎形,成为有机合成和制药应用中有价值的中间体.它的立体特性(1S,4R)配置确保了高度的对应纯度,这对不对称合成和生物活性化合物的发育至关重要.化合物的松散环系统和功能化的拉丁立体能够促成多种反应,特别是在循环和打开环的反应中. 它在标准条件下的稳定性和与一系列试剂的兼容性提高了其在复杂的分子变异中的效用. 这个护具经常被用于天然产品的合成,消毒和受限的外生循环,对立体化学和分子几何学提供了精确的控制.

结构式图片

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79200-56-9 49805-30-3 162427-15-8

欧盟法规

REACH注册C&L通报

上下游产品

2-氮杂双环[2.2.1]庚-5-烯-3-酮 2-Azabicyclo[2.2.1.]Hept-5-En-3-One 49805-30-3
(-)-文斯内酯 (-)-2-Azabicyclo[2.2.1]Hept-5-En-3-One 79200-56-9
2-羟甲基-2-氮杂双环[2.2.1]庚-5-烯-3-酮 2-Hydroxymethyl-2-Azabicyclo<2.2.1>Hept-5-En-3-One 157732-10-0
Racemic N-Hydroxymethyl Vince Lactam

合成工艺路线路线简述

    Cis-1,2,3,6-Tetrahydrophthalic Anhydride置于sodium Tetrahydroborate,Camphor-10-Sulfonic Acid,(4R,5R)-2,2-二甲基-A,A,A',A'-四苯基-1,3-二氧戊环-4,5-二甲醇体系中,用 二氯甲烷 用作溶剂,化学反应 14.0H,反应生成(1S)-(+)-2-氮杂双环[2.2.1]庚-5-烯-3-酮
    参考文献:的非还原对映体选择性开环ñ-二异丙与α,α,α',α'-四芳基-1,3-二氧戊环-4,5-Dimethanolate(甲基磺酰基)二甲
    标题:的非还原对映体选择性开环ñ-二异丙与α,α,α',α'-四芳基-1,3-二氧戊环-4,5-Dimethanolate(甲基磺酰基)二甲
    摘要:二环丙氧基钛taddolate将双环和三环内消旋-N-(甲基磺酰基)二甲酰亚胺1A-F对映体转化为异丙基[(磺酰胺基)羰基]-羧酸盐2A-F(产率为75-92%;参见方案3).产物的对映体比例在86:14至97:3之间,并且从ch 2 Cl 2 /己烷中重结晶得到对映体纯的磺酰胺基酯2(方案3).对映选择性与所用taddol的对映体过量显示线性关系(图3).还原酯基和羧酰胺基(lialh 4)和酰亚胺开环的产物2中磺酰胺基(red-Al)的额外还原裂解分别得到羟基磺酰胺3和氨基醇4(流程4).磺酰胺基酯2的绝对构型是通过化学相关性(与2A,B;方案6),对3E的樟脑酸酯的x射线分析(图1)以及对羟基苯甲酸酯的19 F-NMR分析确定的羟基磺酰胺3的较硬酯(表1).对于伯醇和胺的的绝对构型的分配的一般建议式hxch 2 Chr 1-[r 2,X = O,Nh,建议(见11在表1中).从2
    Doi:10.1002/hlca.19960790328

    海关参考信息

    专利信息


    专利号:US-9334273-B1
    优先权日:2014-03-05
    标题:Efficient and stereoselective synthesis of 2′-fluoro-6′-methylene-carbocyclic adenosine (FMCA)
    发明人:CHU DAVID C K; SINGH UMA S
    权利人:UNIV GEORGIA
    摘要:The invention provides a new convergent approach for the synthesis of 2′-fluoro-6′-methylene-carbocyclic adenosine (FMCA) from a readily available starting material (Vince lactam) in fourteen steps. An efficient and practical methodology for stereospecific preparation of a versatile carbocyclic key intermediate, D -2′-fluoro-6′-methylene cyclopentanol by diazotization, elimination, stereoselective epoxidation, fluorination and oxidative reduction of the Vince lactam in twelve steps is also provided.

    专利号:US-2010204463-A1
    优先权日:2007-08-07
    标题 :Preparation Of Synthetic Nucleosides via Pi-Allyl Transition Metal Complex Formation
    发明人:LIOTTA DENNIS C; LI YONGFENG
    权利人:LIOTTA DENNIS C; LI YONGFENG
    摘要:This invention provides highly regioselective and stereoselective processes for preparing synthetic nucleosides. A process for the preparation of synthetic nucleosides is provided that comprises a) preparing a bicycloamide derivative, b) reacting the bicycloamide derivative with a nucleic acid base or heterocyclic base or salt thereof in the presence of a transition metal catalyst to form a cyclopentenecarboxamide, and c) cleaving a carboxamide group from the cyclopentenecarboxamide to form the synthetic nucleoside. The processes according to the invention can be used for the synthesis of a variety of anti-viral agents, including Abacavir, Carbovir, and Entecavir, as well as derivatives thereof.

    专利号:US-12331006-B2
    优先权日:2018-05-25
    标 题 :Process for the synthesis of (s) 3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid
    发明人:SILVERMAN RICHARD B; MOSCHITTO MATTHEW
    权利人:UNIV NORTHWESTERN
    摘要:Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.

    专利号:EP-3440041-A1
    优先权日:2016-04-07
    标 题:Synthesis of 2'-fluoro-6'-methylene-carbocyclic adenosine (fmca) and 2'-fluoro-6'-methylene-carbocyclic guanosine (fmcg)

    专利号:WO-9703053-A1
    优先权日:1995-07-10
    标题 :N-(acyloxymethyl or hydroxymethyl) (optionally (oxa or thia) substituted)bicyclo([2.2.1] or [2.2.2])azalk(an or en)one compounds
    发明人:PETRE DOMINIQUE; DARNAND ELIANE; MARSEIGNE ISABELLE; LEON PATRICK; BOTANNET DANIELLE
    权利人:RHONE POULENC RORER PHARMA; PETRE DOMINIQUE; DARNAND ELIANE; MARSEIGNE ISABELLE; LEON PATRICK; BOTANNET DANIELLE
    摘要:The present invention is directed to N-(acyloxymethyl or hydroxymethyl)-(optionally (oxa or thia) substituted)bicyclo([2.2.1] or [2.2.2])azalk(an or en)one compounds which are useful as intermediates in the synthesis of cardiovascular agents, including anti-anginal agents, antihypertensives and anti-ischemics, anti-viral agents, anti-neoplastic agents, antifungal agents and antimicrobial agents, and to their preparation.

    专利号:EP-4410773-A2
    优先权日:2018-05-25
    标 题:Process for the synthesis of (s) 3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid
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    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    [参考文献]: R Vince, Et Al. Synthesis And Anti-Hiv Activity Of Carbocyclic 2',3'-Didehydro-2',3'-Dideoxy 2,6-Disubstituted Purine Nucleosides. J Med Chem. 1990 Jan;33(1):17-21.

    合成参考文献


    摘要:Hall, M.; Faber, K.; Tasnádi, G., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 1, 317.
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