(4R,5R,7S,8S,12R)-4,7-Dihydroxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester | 503546-24-5

• 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: (4R,5R,7S,8S,12R)-4,7-Dihydroxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester
• 英文别名: methyl (4R,5R,7S,8S,12R)-4,7-dihydroxy-8,12-dimethyl-5-propan-2-yl-15-oxabicyclo[12.1.0]pentadecane-2-carboxylate
• CAS: 503546-24-5
• 化学式: C₂₁H₃₈O₅
• 分子量: 370.53
• InChiKey: PCDAECSUILZAEP-SCNXEXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R,7S,8S,12R)-4,7-Dihydroxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 11.0h， 生成 (E)-(5R,9S,10S,12R,13R)-12-Isopropyl-5,9-dimethyl-3-oxo-10,13-bis-trimethylsilanyloxy-cyclotetradec-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 2: SmI2-mediated 14-membered carbocyclization

  摘要：

  The dienophile unit of methyl isosartortuoate has been synthesized. The 14-membered carbocycle was constructed by a SmI2-mediated intramolecular Reformatsky reaction. The introduction of the oxo group at the gamma-position of the alpha,beta-unsaturated ester was achieved by rearrangement of an beta,gamma-epoxy ester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02603-5
• 作为产物：
  描述：

  (4R,5R,7S,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以70%的产率得到(4R,5R,7S,8S,12R)-4,7-Dihydroxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies on the dienophile unit of methyl isosartortuoate. Part 2: SmI2-mediated 14-membered carbocyclization

  摘要：

  The dienophile unit of methyl isosartortuoate has been synthesized. The 14-membered carbocycle was constructed by a SmI2-mediated intramolecular Reformatsky reaction. The introduction of the oxo group at the gamma-position of the alpha,beta-unsaturated ester was achieved by rearrangement of an beta,gamma-epoxy ester. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02603-5