methyl 2-[[(1R)-1-phenylethyl]amino]cyclohexene-1-carboxylate | 163394-56-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 2-[[(1R)-1-phenylethyl]amino]cyclohexene-1-carboxylate
• CAS: 163394-56-7
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: XTNPNWCKXYQQDG-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(1R)-1-phenylethyl]amino]cyclohexene-1-carboxylate 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 、 三乙酰氧基硼氢化钠 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 生成 2,2,2-trifluoroacetic acid; methyl (1S,2R)-2-[(2S)-2-(5-carbamimidoyl-1-benzothiophen-3-yl)-3-phenylpropanamido]cyclohexane-1-carboxylate
  参考文献：
  名称：

  5-Amidinobenzo[b]thiophenes as dual inhibitors of factors IXa and Xa

  摘要：

  Syntheses and SAR studies of 5-amidinobenzo[b]thiophene analogs provided compounds with low submicromolar factor IXa activity and equal or slightly better selectivity relative to factor Xa. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.045
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 2-氧环己烷羧酸甲酯 以 苯 为溶剂， 反应 12.0h， 以86%的产率得到methyl 2-[[(1R)-1-phenylethyl]amino]cyclohexene-1-carboxylate
  参考文献：
  名称：

  Methyl methacrylate as acceptor in the asymmetric Michael reaction using chiral β-enaminoesters: Simultaneous, complete stereocontrol of a quaternary carbon center and a tertiary one in the β-position

  摘要：

  Addition of enaminoester (R)-7 to methyl methacrylate 8 led to adduct (2S, 1'R)-9 with a complete stereoselectivity.

  DOI：

  10.1016/0957-4166(94)00356-g

文献信息

• Stereochemical Aspects in the Asymmetric Michael Addition of Chiral Imines to Substituted Electrophilic Alkenes
  作者：Christian Cavé,、Didier Desmaële、Jean d'Angelo、Claude Riche、Angèle Chiaroni

  DOI：10.1021/jo960140k

  日期：1996.1.1

  behavior of a variety of alpha- and beta-substituted alkenyl acceptors was examined. In general, these additions are highly regioselective, the alkylation taking place predominantly, if not exclusively, at the more substituted alpha-side of the imine function; however, in some cases (electrophilic alkenes 28 and 49), significant amounts (10-15%) of regioisomeric adducts were obtained. With the exception

  在中性条件下，将由外消旋α-取代的环酮和光学活性的1-苯基乙胺衍生的手性亚胺的迈克尔型加成到亲电子烯烃中，构成了季碳中心立体控制结构的最有效方法之一。为了在四级α-或β-位置上创建另一个立体中心，研究了各种α-和β-取代烯基受体的行为。通常，这些添加是高度区域选择性的，烷基化主要发生在亚胺官能团的更被取代的α-侧，如果不是唯一的话。然而，在某些情况下（亲电烯烃28和49），获得了大量（10-15％）的区域异构加合物。除了丙酸甲酯52 这些迈克尔受体总是观察到对加合物绝对构型的显着控制。根据我们先前提出的一般规则，在与起始亚胺的互变异构平衡中，烷基化过程优先发生在取代度更高的仲烯胺的较少受阻pi面上。通过使用本发明的α-和β-取代的烯烃，总是获得优异的非对映异构控制。这些立体化学结果可以通过调用反应物的紧密途径来解释，烯胺氮中心的氢原子被转移到受体的α-乙烯基碳原子上，与CC的形成协调一致。键。在这方面，“内在方法”
• Desmaele, Didier; Cave, Christian; Dumas, Francoise, Enantiomer, 2001, vol. 6, # 5, p. 289 - 298
  作者：Desmaele, Didier、Cave, Christian、Dumas, Francoise、d'Angelo, Jean

  DOI：——

  日期：——
• Methyl methacrylate as acceptor in the asymmetric Michael reaction using chiral β-enaminoesters: Simultaneous, complete stereocontrol of a quaternary carbon center and a tertiary one in the β-position
  作者：Christian Cavé、Valérie Daley、Jean d'Angelo、André Guingant

  DOI：10.1016/0957-4166(94)00356-g

  日期：1995.1

  Addition of enaminoester (R)-7 to methyl methacrylate 8 led to adduct (2S, 1'R)-9 with a complete stereoselectivity.
• 5-Amidinobenzo[b]thiophenes as dual inhibitors of factors IXa and Xa
  作者：Jennifer X. Qiao、Xuhong Cheng、Dilip P. Modi、Karen A. Rossi、Joseph M. Luettgen、Robert M. Knabb、Prabhakar K. Jadhav、Ruth R. Wexler

  DOI：10.1016/j.bmcl.2004.10.045

  日期：2005.1

  Syntheses and SAR studies of 5-amidinobenzo[b]thiophene analogs provided compounds with low submicromolar factor IXa activity and equal or slightly better selectivity relative to factor Xa. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE
  作者：Prabal Sengupta、Chetan S. Puri、Hemant A. Chokshi、Chetana K. Sheth、Ajay S. Midha、Trinadha Rao Chitturi、Rajamannar Thennati、Prashant R. Murumkar、Mange Ram Yadav

  DOI：10.1016/j.ejmech.2011.09.018

  日期：2011.11

  Central heteroaryl ring analogues belonging to a series of potent hydroxamate TACE inhibitors were synthesized. The TACE inhibitory activities of these compounds were evaluated by in vitro WBA and in silico molecular modeling studies using crystal structure of human TACE. Compound 14 showed very good in vitro inhibition, supported by the in silico docking studies. (C) 2011 Elsevier Masson SAS. All rights reserved.