dimethyl <4-acetoxy-2E-butenyl>-3-butenylmalonate | 158627-80-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl <4-acetoxy-2E-butenyl>-3-butenylmalonate
• 英文别名: dimethyl (4-acetoxy-2E-butenyl)-3-butenylmalonate
• CAS: 158627-80-6
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: GVQJJGMGJTXLCG-BQYQJAHWSA-N

物化性质

• 沸点：
  365.9±42.0 °C(predicted)
• 密度：
  1.083±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 dimethyl <4-acetoxy-2E-butenyl>-3-butenylmalonate 在 tris(triphenylphosphano)palladium 作用下， 以 溶剂黄146 为溶剂， 80.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 生成 (3aS,7aS)-3-Methylene-2-oxo-octahydro-indene-5,5-dicarboxylic acid dimethyl ester 、 (3aS,7aR)-3-Methylene-2-oxo-octahydro-indene-5,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8
• 作为产物：
  描述：

  dimethyl <4-(2'-tetrahydropyranyloxy)-2E-butenyl>-3-butenylmalonate 在 吡啶 、 甲醇 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 dimethyl <4-acetoxy-2E-butenyl>-3-butenylmalonate
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8

文献信息

• Formation of α,β-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols
  作者：Enrique Gómez-Bengoa、Pedro Noheda、Antonio M. Echavarren

  DOI：10.1016/0040-4039(94)88235-5

  日期：1994.9

  Treatment of allylic alcohols with catalytic amounts of palladium catalysts in the presence of oxygen leads to the formation of α,β-unsaturated carbonyl compounds.

  在氧气存在下用催化量的钯催化剂处理烯丙醇会导致形成α，β-不饱和羰基化合物。