ethyl (E)-(N-benzyltrifluoroacetamido)pent-2-enoate | 112532-94-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-(N-benzyltrifluoroacetamido)pent-2-enoate
• 英文别名: ethyl 5-(N-benzyltrifluoroacetamido)-2-pentenoate；ethyl (E)-5-[benzyl-(2,2,2-trifluoroacetyl)amino]pent-2-enoate
• CAS: 112532-94-2
• 化学式: C₁₆H₁₈F₃NO₃
• 分子量: 329.319
• InChiKey: RFNGQPCLVMUTCL-UXBLZVDNSA-N

物化性质

• 沸点：
  437.2±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-(N-benzyltrifluoroacetamido)pent-2-enoate 在 4 A molecular sieve 、 potassium carbonate 作用下， 以 乙醇 、 苯 为溶剂， 反应 15.5h， 生成 trans-1-benzyl-3-(ethoxycarbonylmethyl)-2-(3-chlorophenyl)pyrrolidine
  参考文献：
  名称：

  Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C C bonds

  摘要：

  2,3-Disubstituted pyrrolidines are prepared by SmI2-pranoted cyclization of alpha-amino radicals generated from N-(alpha-benzotriazolylalkyl)alkenylamines containing a C=C bond activated by an electron withdrawing substituent. The diastereoselectivity of cyclization is moderate and depends on the nature of the substituent at the pyrrolidine 2-position. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00359-2
• 作为产物：
  描述：

  N-benzyl-N-(but-3-enyl)-2,2,2-trifluoroacetamide 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 ethyl (E)-(N-benzyltrifluoroacetamido)pent-2-enoate
  参考文献：
  名称：

  Synthesis of 2,3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C C bonds

  摘要：

  2,3-Disubstituted pyrrolidines are prepared by SmI2-pranoted cyclization of alpha-amino radicals generated from N-(alpha-benzotriazolylalkyl)alkenylamines containing a C=C bond activated by an electron withdrawing substituent. The diastereoselectivity of cyclization is moderate and depends on the nature of the substituent at the pyrrolidine 2-position. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00359-2

文献信息

• A stereocontrolled synthesis of (.+-.)-emetine and (.+-.)-protoemetinol by intramolecular michael reaction.
  作者：YOSHIRO HIRAI、TAKASHI TERADA、ATSUSHI HAGIWARA、TAKAO YAMAZAKI

  DOI：10.1248/cpb.36.1343

  日期：——

  An intramolecular Michael reaction of 9 stereoselectively gave the tricyclic compound (10), which was converted to (±)-protoemetinol (2) and 13. Compound 13 is an important intermediate for the synthesis of (±)-emetine. A simpler preparation of 13 was also carried out by the intramolecular Michael reaction of 14, followed by reduction of the ketone moietv. Furthermore, the stereoselective formation of 26, which is an intermediate for the synthesis of (±)-emetine, was achieved by the floowing sequence of reactions : intramolecular Michael reaction, of the ketone moiety, and removal of the N-carbomethoxy group.

  9 的分子内迈克尔反应立体选择性地生成了三环化合物 (10)，然后转化为 (±)-protoemetinol (2) 和 13。化合物 13 是合成(±)-美丁的重要中间体。通过 14 的分子内迈克尔反应，然后还原酮莫埃特 v，也可以更简单地制备 13。此外，通过以下反应顺序：分子内迈克尔反应、酮基反应和去除 N-甲酰甲氧基反应，立体选择性地生成了 26，它是合成(±)-甜菜碱的中间体。
• HIRAI, YOSHIRO;TERADA, TAKASHI;HAGIWARA, ATSUSHI;YAMAZAKI, TAKAO, CHEM. AND PHARM. BULL., 36,(1988) N 4, 1343-1350
  作者：HIRAI, YOSHIRO、TERADA, TAKASHI、HAGIWARA, ATSUSHI、YAMAZAKI, TAKAO

  DOI：——

  日期：——