(2E)-ethyl 2-bromo-5-phenylpent-2-en-4-ynoate | 208194-62-1

• 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: (2E)-ethyl 2-bromo-5-phenylpent-2-en-4-ynoate
• 英文别名: ethyl (E)-2-bromo-5-phenylpent-2-en-4-ynoate
• CAS: 208194-62-1
• 化学式: C₁₃H₁₁BrO₂
• 分子量: 279.133
• InChiKey: GPLDFXMBNQKORY-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (2E)-ethyl 2-bromo-5-phenylpent-2-en-4-ynoate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-2-bromo-5-phenylpent-2-en-4-ynoic acid
  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：

  反-2,3-二溴丙烯酸乙酯 、 (苯乙炔基)氯化锌 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(2E)-ethyl 2-bromo-5-phenylpent-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 Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols
  作者：Usama Karama、Zeid Al-Othman、Abdullah Al-Majid、Abdulrahman Almansour

  DOI：10.3390/molecules15053276

  日期：——

  in CH2Cl2 followed by the addition of an alcohol in the presence of manganese dioxide under ultrasonic irradiation constitutes a stereoselective one-pot procedure for the preparation of Z-configured α–bromo-α,β-unsaturated esters in good to excellent yield.

  在 CH2Cl2 中用（碳乙氧基亚甲基）三苯基正膦（1）处理 N-溴代琥珀酰亚胺（NBS），然后在二氧化锰的存在下在超声波照射下加入醇，构成了一种立体选择性的一锅法制备 Z-构型的 α-溴-α,β-不饱和酯的产率非常好。