methyl 2-{[(R)-1-phenylethyl]amino}cyclopent-1-ene-1-carboxylate | 683774-02-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 2-{[(R)-1-phenylethyl]amino}cyclopent-1-ene-1-carboxylate
• 英文别名: methyl (1'R) 2-[(1-phenylethyl)amino]-1-cyclopentene-1-carboxylate；methyl 2-[[(1R)-1-phenylethyl]amino]cyclopentene-1-carboxylate
• CAS: 683774-02-9
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: FZLMJZDFCJTCEF-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-{[(R)-1-phenylethyl]amino}cyclopent-1-ene-1-carboxylate 在 盐酸 、 lithium hydroxide 、 cerium(III) chloride 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 55.0h， 生成 (4aR,7aS)-2-oxo-3,4,5,6,7,7a-hexahydrocyclopenta[b]pyran-4a-carboxylic acid
  参考文献：
  名称：

  Enantioselective Synthesis of (R)-1-Azaspiro[4.4]nonane-2,6-dione Ethylene Ketal, Key Chiral Intermediate in the Elaboration of (-)-Cephalotaxine

  摘要：

  DOI：

  10.3987/com-05-s(k)3
• 作为产物：
  描述：

  环戊酮 在 lithium hexamethyldisilazane 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.17h， 生成 methyl 2-{[(R)-1-phenylethyl]amino}cyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis, preliminary biological evaluation and molecular modeling of some new heterocyclic inhibitors of TACE

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.09.018

文献信息

• Total Synthesis of (-)-13-Acetoxymodhephene and (+)-14-Acetoxymodhephene
  作者：Hee-Yoon Lee、Ravichandran N. Murugan、Deuk Kyu Moon

  DOI：10.1002/ejoc.200900713

  日期：2009.10

  Stereoselective epoxidation of [4.3.3]propellane 16 set the stage for the Lewis acid catalyzed stereospecific ring contraction to an oxygenated modhephene structure and eventually led to the total synthesis of (–)-13-acetoxymodhephene and (+)-14-acetoxymodhephene. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  [4.3.3]propellane 16 的立体选择性环氧化为路易斯酸催化立体定向环收缩为含氧摩茚结构奠定了基础，并最终导致 (-)-13-乙酰氧基摩茚和 (+)-14-乙酰氧基摩茚的全合成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Asymmetric catalytic hydrogenation process for preparation of chiral cyclic beta-aminoesters
  申请人：——

  公开号：US20040082795A1

  公开（公告）日：2004-04-29

  A novel process for the asymmetric synthesis of substituted cyclic &bgr;-amino-carboxylates of the type shown in the specification from appropriate &bgr;-enamino-ester starting materials is described. These compounds are useful as intermediates for MMP and TACE inhibitors.

  本文介绍了一种新颖的方法，用于从适当的β-烯酰胺酯起始材料不对称合成规范中所示的取代环状β-氨基羧酸酯。这些化合物可用作MMP和TACE抑制剂的中间体。
• 10.3998/ark.5550190.0018.400
  作者：Seck, Rokhayatou、Gassama, Abdoulaye、Nour, Mohammed、Demange, Luc、Cavé, Christian

  DOI：10.3998/ark.5550190.0018.400

  日期：——
• The asymmetric Michael-type alkylation of chiral β-enamino esters: critical role of a benzyl ester group in the racemization of adducts
  作者：Mathieu Pizzonero、Frédéric Hendra、Sandrine Delarue-Cochin、Marie-Elise Tran Huu-Dau、Françoise Dumas、Christian Cavé、Mohammed Nour、Jean d’Angelo

  DOI：10.1016/j.tetasy.2005.10.034

  日期：2005.11

  In contrast with keto diester (R)-10a bearing a methyl ester group at the quaternary carbon center, the benzyl ester analogue (R)-10a partially racemized during workup, thereby revealing that the nature of the ester group at the quaternary carbon center has a critical role in the rate of racemization of such Michael adducts. (c) 2005 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.