ethyl (E)-2-bromo-3-methylnon-2-en-4-ynoate | 208194-65-4

• 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)-2-bromo-3-methylnon-2-en-4-ynoate
• CAS: 208194-65-4
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: DJEKCPCLUROGOI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-bromo-3-methylnon-2-en-4-ynoate 在 二(氰基苯)二氯化钯 、 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) N-甲基吡咯烷酮 、 lithium hydroxide 、 copper(l) iodide 、 三苯胂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 72.0h， 生成 (5Z)-3,4-二甲基-5-戊亚基-2(5H)-呋喃酮
  参考文献：
  名称：

  A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

  摘要：

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00322-0
• 作为产物：
  描述：

  Dibromo-2,3-crotonsaeureethylester 、 chlorozinc(1+),hex-1-yne 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到ethyl (E)-2-bromo-3-methylnon-2-en-4-ynoate
  参考文献：
  名称：

  A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

  摘要：

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00322-0

文献信息

• A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones
  作者：Renzo Rossi、Fabio Bellina、Luisa Mannina

  DOI：10.1016/s0040-4039(98)00322-0

  日期：1998.5

  The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4-(1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan-2-ones, 9. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylideng-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide. (C) 1998 Elsevier science Ltd. All rights reserved.