2-(Diphenoxy-phosphoryl)-6-methyl-5-[1-[(1R,5S,8S)-1-(1-methylene-4-oxo-butyl)-3-oxo-2,4-dioxa-bicyclo[3.2.1]oct-8-yl]-meth-(E)-ylidene]-heptanoic acid methyl ester | 1027055-66-8

• 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: 2-(Diphenoxy-phosphoryl)-6-methyl-5-[1-[(1R,5S,8S)-1-(1-methylene-4-oxo-butyl)-3-oxo-2,4-dioxa-bicyclo[3.2.1]oct-8-yl]-meth-(E)-ylidene]-heptanoic acid methyl ester
• 英文别名: methyl (5E)-2-diphenoxyphosphoryl-6-methyl-5-[[(1R,5S,8S)-3-oxo-1-(5-oxopent-1-en-2-yl)-2,4-dioxabicyclo[3.2.1]octan-8-yl]methylidene]heptanoate
• CAS: 1027055-66-8
• 化学式: C₃₃H₃₉O₉P
• 分子量: 610.641
• InChiKey: ZKMTYXCZHCULST-XJKARSECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(Diphenoxy-phosphoryl)-6-methyl-5-[1-[(1R,5S,8S)-1-(1-methylene-4-oxo-butyl)-3-oxo-2,4-dioxa-bicyclo[3.2.1]oct-8-yl]-meth-(E)-ylidene]-heptanoic acid methyl ester 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 20.0h， 生成 (7Z,11E)-(1S,3aR,12aS)-1,3a-Dihydroxy-11-isopropyl-4-methylene-1,2,3,3a,4,5,6,9,10,12a-decahydro-cyclopentacycloundecene-8-carboxylic acid
  参考文献：
  名称：

  Total synthesis of 6-epi-sarsolilide A

  摘要：

  This paper describes an asymmetric synthesis of 6-epi-sarsolilide A. The 11-membered carbocycle and seven-membered lactone were established by an intramolecular HWE reaction and iodolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02126-7
• 作为产物：
  描述：

  5-[1-[(1R,5S,8S)-1-(4,4-Dimethoxy-1-methylene-butyl)-3-oxo-2,4-dioxa-bicyclo[3.2.1]oct-8-yl]-meth-(E)-ylidene]-2-(diphenoxy-phosphoryl)-6-methyl-heptanoic acid methyl ester 在 amberlyst-15 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-(Diphenoxy-phosphoryl)-6-methyl-5-[1-[(1R,5S,8S)-1-(1-methylene-4-oxo-butyl)-3-oxo-2,4-dioxa-bicyclo[3.2.1]oct-8-yl]-meth-(E)-ylidene]-heptanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of 6-epi-sarsolilide A

  摘要：

  This paper describes an asymmetric synthesis of 6-epi-sarsolilide A. The 11-membered carbocycle and seven-membered lactone were established by an intramolecular HWE reaction and iodolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02126-7

文献信息

• Total synthesis of 6-epi-sarsolilide A
  作者：Jiazhong Zhang、Xingxiang Xu

  DOI：10.1016/s0040-4039(99)02126-7

  日期：2000.2

  This paper describes an asymmetric synthesis of 6-epi-sarsolilide A. The 11-membered carbocycle and seven-membered lactone were established by an intramolecular HWE reaction and iodolactonization. (C) 2000 Elsevier Science Ltd. All rights reserved.