ethyl (E)-2-bromo-3-<(2-methoxymethoxy)phenyl>-2-butenoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-2-bromo-3-<(2-methoxymethoxy)phenyl>-2-butenoate
• 英文别名: ethyl (E)-2-bromo-3-[2-(methoxymethoxy)phenyl]but-2-enoate
• 化学式: C₁₄H₁₇BrO₄
• 分子量: 329.191
• InChiKey: LRBABWRXCAKGRV-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-bromo-3-<(2-methoxymethoxy)phenyl>-2-butenoate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到3-bromo-4-hydroxycoumarin
  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
• 作为产物：
  描述：

  Dibromo-2,3-crotonsaeureethylester 、 (2-methoxymethoxy)phenylzinc chloride 在 palladium diacetate 、 三苯胂 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以24%的产率得到ethyl (E)-2-bromo-3-<(2-methoxymethoxy)phenyl>-2-butenoate
  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

文献信息

• Palladium-mediated cross-coupling reactions involving 3-substituted alkyl (E)-2,3-dibromopropenoates and arylzinc or aryltin derivatives
  作者：Renzo Rossi、Fabio Bellina、Adriano Carpita、Felice Mazzarella

  DOI：10.1016/s0040-4020(96)00071-3

  日期：1996.3

  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.