(S)-ethyl-2-(2-(2-(bromomethyl)acrylamido)-4-methylpentaneamido)acetate | 1371607-59-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-ethyl-2-(2-(2-(bromomethyl)acrylamido)-4-methylpentaneamido)acetate
• 英文别名: ethyl 2-[[(2S)-2-[2-(bromomethyl)prop-2-enoylamino]-4-methylpentanoyl]amino]acetate
• CAS: 1371607-59-8
• 化学式: C₁₄H₂₃BrN₂O₄
• 分子量: 363.252
• InChiKey: GXHXWYAXHCIGLV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-bis(trifluoromethyl)benzoic acid cesium salt 、 (S)-ethyl-2-(2-(2-(bromomethyl)acrylamido)-4-methylpentaneamido)acetate 以 丙酮 为溶剂， 反应 2.0h， 以33%的产率得到2,6-bis-trifluoromethylobenzoic acid 2-[1-(ethoxycabonylmethylcarbamoyl)-3-methylbutylcarbamoyl]allyl ester
  参考文献：
  名称：

  [EN] NOVEL ESTERS OF (ACYLOXYMETHYL)ACRYLAMIDE, A PHARMACEUTICAL COMPOSITION CONTAINING THEM, AND THEIR USE AS INHIBITORS OF THE THIOREDOXIN - THIOREDOXIN REDUCTASE SYSTEM
  [FR] NOUVEAUX ESTERS D'(ACYLOXYMÉTHYL)ACRYLAMIDE, COMPOSITION PHARMACEUTIQUE LES CONTENANT, ET LEUR UTILISATION EN TANT QU'INHIBITEURS DU SYSTÈME DE THIORÉDOXINE/THIORÉDOXINE RÉDUCTASE

  摘要：

  本发明的主题是新的（酰氧甲基）丙烯酰胺酯，其中包含它们的制药组合物以及它们在生产用于预防或治疗肿瘤性疾病和与细胞增殖增加有关的疾病的药物中的应用。

  公开号：

  WO2012050465A1
• 作为产物：
  描述：

  ethyl 2-[2-{2-(bromomethyl)-N-(1-{2,4-dimethoxyphenyl}ethyl)acrylamido}-4-methylpentanamido]acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-ethyl-2-(2-(2-(bromomethyl)acrylamido)-4-methylpentaneamido)acetate
  参考文献：
  名称：

  Chemoenzymatic synthesis and application of a new, easily chiral auxiliary for the synthesis of peptidomimetics via an Ugi reaction

  摘要：

  A new chiral auxiliary derived from alpha-phenylethylamine, alpha-(2,4-dimethoxyphenyl)ethylamine is presented. It significantly expands upon the application of cc-phenylethylamine derivatives used as chiral auxiliaries. A straightforward, chemoenzymatic synthesis of non-racemic alpha-(2,4-dimethoxyphenyl)ethylamine is described and the new chiral auxiliary applied to an asymmetric Ugi reaction. The mild conditions used for the cleavage of the auxiliary allowed to obtain chiral, non-racemic peptidomimetics possessing reactive alpha,beta-unsaturated double bonds.(C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.016

文献信息

• [EN] NOVEL ESTERS OF (ACYLOXYMETHYL)ACRYLAMIDE, A PHARMACEUTICAL COMPOSITION CONTAINING THEM, AND THEIR USE AS INHIBITORS OF THE THIOREDOXIN - THIOREDOXIN REDUCTASE SYSTEM<br/>[FR] NOUVEAUX ESTERS D'(ACYLOXYMÉTHYL)ACRYLAMIDE, COMPOSITION PHARMACEUTIQUE LES CONTENANT, ET LEUR UTILISATION EN TANT QU'INHIBITEURS DU SYSTÈME DE THIORÉDOXINE/THIORÉDOXINE RÉDUCTASE
  申请人：INST CHEMII ORGANICZNEJ POLSKIEJ AKADEMII NAUK

  公开号：WO2012050465A1

  公开（公告）日：2012-04-19

  The subject of the present invention are novel esters of (acyloxymethyl)acrylamide, a pharmaceutical composition containing them and their use in the production of drugs for the prophylaxis or treatment of oncogenic diseases and diseases connected with increased cell proliferation.

  本发明的主题是新的（酰氧甲基）丙烯酰胺酯，其中包含它们的制药组合物以及它们在生产用于预防或治疗肿瘤性疾病和与细胞增殖增加有关的疾病的药物中的应用。
• Chemoenzymatic synthesis and application of a new, easily chiral auxiliary for the synthesis of peptidomimetics via an Ugi reaction
  作者：Szymon Klossowski、Anna Brodzka、Małgorzata Zysk、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2014.01.016

  日期：2014.3

  A new chiral auxiliary derived from alpha-phenylethylamine, alpha-(2,4-dimethoxyphenyl)ethylamine is presented. It significantly expands upon the application of cc-phenylethylamine derivatives used as chiral auxiliaries. A straightforward, chemoenzymatic synthesis of non-racemic alpha-(2,4-dimethoxyphenyl)ethylamine is described and the new chiral auxiliary applied to an asymmetric Ugi reaction. The mild conditions used for the cleavage of the auxiliary allowed to obtain chiral, non-racemic peptidomimetics possessing reactive alpha,beta-unsaturated double bonds.(C) 2014 Elsevier Ltd. All rights reserved.