Dibromo-2,3-crotonsaeureethylester | 28113-30-6

• 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: Dibromo-2,3-crotonsaeureethylester
• 英文别名: ethyl (E)-2,3-dibromobut-2-enoate
• CAS: 28113-30-6
• 化学式: C₆H₈Br₂O₂
• 分子量: 271.936
• InChiKey: GKWIFQOOTHLWNE-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  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
• 作为产物：
  描述：

  2-丁炔酸乙酯 在 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 192.0h， 以98%的产率得到Dibromo-2,3-crotonsaeureethylester
  参考文献：
  名称：

  Palladium-mediated cross-coupling reactions involving 3-substituted alkyl (E)-2,3-dibromopropenoates and arylzinc or aryltin derivatives

  摘要：

  Stereodefined unsymmetrically 3,3-disubstituted alkyl 2-bromopropenoates, 5, were regioselectively prepared by Pd-mediated reactions between 3-alkyl, 3-aryl and 3-alkoxycarbonyl substituted (E)-2,3-dibromopropenoates, (E)-7, and aryl or 1-alkynylzinc chlorides. The stereospecificity of these reactions was found to be dependent on the type of substituent present in the 3-position of (E)-7. The (E)-stereochemistry of compounds 5b, 5d and 5i so prepared was confirmed by their conversion into the corresponding 4-substituted 3-bromocoumarins. Tetrasubstituted alpha,beta-unsaturated esters 10 were then synthesized by Pd-mediated reactions either of (E)-7 with a molar excess of an arylzinc chloride or an aryltributylstannane, or of a compound of general formula 5 with an aryltributylstannane. An examination of the parameters which influence the stereochemistry and the yields of these arylations was made.

  DOI：

  10.1016/s0040-4020(96)00071-3