cis-4-bromo-2-butenoic acid methyl ester | 56699-18-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: cis-4-bromo-2-butenoic acid methyl ester
• 英文别名: methyl (Z)-4-bromo-but-2-enoate；methyl (Z)-4-bromo-2-butenoate；methyl 4-bromobut-2-enoate；(Z)-Methyl 4-bromobut-2-enoate；methyl (Z)-4-bromobut-2-enoate
• CAS: 56699-18-4
• 化学式: C₅H₇BrO₂
• 分子量: 179.013
• InChiKey: RWIKCBHOVNDESJ-IHWYPQMZSA-N

物化性质

• 沸点：
  198.5±0.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  cis-4-bromo-2-butenoic acid methyl ester 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.25h， 生成 methyl (E)-4-(2-formylphenoxy)but-2-enoate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074
• 作为产物：
  描述：

  顺丁烯二酸单甲酯 在 硼烷四氢呋喃络合物 、 三乙胺 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 cis-4-bromo-2-butenoic acid methyl ester
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074

文献信息

• Ward, Yancey D.; Villanueva, Lawrence A.; Allred, Gary D., Organometallics, 1995, vol. 14, # 9, p. 4132 - 4156
  作者：Ward, Yancey D.、Villanueva, Lawrence A.、Allred, Gary D.、Payne, Sonha C.、Semones, Mark A.、Liebeskind, Lanny S.

  DOI：——

  日期：——
• Geminal Silicon/Zinc Reagent as an Equivalent of Difluoromethylene Bis-carbanion
  作者：Mikhail D. Kosobokov、Vitalij V. Levin、Artem A. Zemtsov、Marina I. Struchkova、Alexander A. Korlyukov、Dmitry E. Arkhipov、Alexander D. Dilman

  DOI：10.1021/ol5002297

  日期：2014.3.7

  A new difluorinated reagent, [difluoro(trimethylsilyl)methyl]zinc bromide, bearing C-Zn and C-Si bonds is described. The reagent is conveniently prepared by cobalt-catalyzed halogen/zinc exchange. It can be coupled with two different C-electrophiles in a stepwise manner (with allylic halides for C-Zn bond and aldehydes for C-Si bond) affording products containing a difluoromethylene fragment.
• Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations
  作者：Jiří Pospíšil、Milan Potáček

  DOI：10.1016/j.tet.2006.10.074

  日期：2007.1

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.