dimethyl 1-(3-acetoxy-4-pentenyl)-(2-propenyl)malonate | 158627-76-0

• 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: dimethyl 1-(3-acetoxy-4-pentenyl)-(2-propenyl)malonate
• CAS: 158627-76-0
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: FQVMNFDZCOOVFK-UHFFFAOYSA-N

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 1-(3-acetoxy-4-pentenyl)-(2-propenyl)malonate 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 2-((E)-5-Acetoxy-pent-3-enyl)-2-allyl-malonic acid dimethyl ester 、 (3aR,7aR)-1-Methylene-2-oxo-octahydro-indene-5,5-dicarboxylic acid dimethyl ester 、 (3aR,7aS)-1-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 1-(3-(2'-tetrahydropyranyloxy)-4-pentenyl)-(2-propenyl)malonate 在 吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 dimethyl 1-(3-acetoxy-4-pentenyl)-(2-propenyl)malonate
  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