3-<3-(4-Chloro-3-oxobutyl)-2,4,4-trimethyl-5-oxo-1(6)-cyclohexenyl>propanoic acid | 151775-32-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-<3-(4-Chloro-3-oxobutyl)-2,4,4-trimethyl-5-oxo-1(6)-cyclohexenyl>propanoic acid
• 英文别名: 3-[3-(4-Chloro-3-oxobutyl)-2,2,4-trimethyl-5-oxocyclohex-3-en-1-yl]propanoic acid
• CAS: 151775-32-5
• 化学式: C₁₆H₂₃ClO₄
• 分子量: 314.809
• InChiKey: WGRNIVVQDRVKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<3-(4-Chloro-3-oxobutyl)-2,4,4-trimethyl-5-oxo-1(6)-cyclohexenyl>propanoic acid 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以59%的产率得到12,14,14-Trimethyl-5-oxobicyclo<8.3.1>tetradeca-12-ene-3,6,11-trione
  参考文献：
  名称：

  Macrolactonization-transannular aldol condensation approach to the taxane AB ring system

  摘要：

  Cyclohexenone 13, containing the fully elaborated taxane A ring, was prepared from 4,4-dimethyl-2-cyclohexenone (43% for four steps); two copper-catalyzed Grignard conjugate addition reactions on crowded dienones 8 and 11 were employed as key transformations. Elaboration of 13 to the chloro keto acid 6 was achieved via an epoxidation/regioselective chloride-mediated epoxide ring opening/Jones oxidation protocol (42% for three steps). Macrolactonization (59%) followed by chemoselective transannular aldol condensation within the resulting 11-membered bicyclic keto lactone 4 under thermodynamic control (51%) resulted in closure of the taxane B ring to afford the target 2(5H)-furanone 3.

  DOI：

  10.1021/jo00076a049
• 作为产物：
  描述：

  3-(3-Butenyl)-5-<2-(1,3-dioxan-2-yl)ethyl>-2,4,4-trimethyl-2-cyclohexenone 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 、 间氯过氧苯甲酸 、 lithium chloride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 70.0h， 生成 3-<3-(4-Chloro-3-oxobutyl)-2,4,4-trimethyl-5-oxo-1(6)-cyclohexenyl>propanoic acid
  参考文献：
  名称：

  Macrolactonization-transannular aldol condensation approach to the taxane AB ring system

  摘要：

  Cyclohexenone 13, containing the fully elaborated taxane A ring, was prepared from 4,4-dimethyl-2-cyclohexenone (43% for four steps); two copper-catalyzed Grignard conjugate addition reactions on crowded dienones 8 and 11 were employed as key transformations. Elaboration of 13 to the chloro keto acid 6 was achieved via an epoxidation/regioselective chloride-mediated epoxide ring opening/Jones oxidation protocol (42% for three steps). Macrolactonization (59%) followed by chemoselective transannular aldol condensation within the resulting 11-membered bicyclic keto lactone 4 under thermodynamic control (51%) resulted in closure of the taxane B ring to afford the target 2(5H)-furanone 3.

  DOI：

  10.1021/jo00076a049

文献信息

• Macrolactonization-transannular aldol condensation approach to the taxane AB ring system
  作者：Ki Byung Chai、Paul Sampson

  DOI：10.1021/jo00076a049

  日期：1993.11

  Cyclohexenone 13, containing the fully elaborated taxane A ring, was prepared from 4,4-dimethyl-2-cyclohexenone (43% for four steps); two copper-catalyzed Grignard conjugate addition reactions on crowded dienones 8 and 11 were employed as key transformations. Elaboration of 13 to the chloro keto acid 6 was achieved via an epoxidation/regioselective chloride-mediated epoxide ring opening/Jones oxidation protocol (42% for three steps). Macrolactonization (59%) followed by chemoselective transannular aldol condensation within the resulting 11-membered bicyclic keto lactone 4 under thermodynamic control (51%) resulted in closure of the taxane B ring to afford the target 2(5H)-furanone 3.