ethyl (E)-4-[(1R,2S,6S,8R,9R,10S)-10-(methoxymethoxy)-2,5,9-trimethyl-3-oxotricyclo[6.3.0.0(2,6)]undec-4-en-6-yl]but-2-enoate | 1370591-81-3

• 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: ethyl (E)-4-[(1R,2S,6S,8R,9R,10S)-10-(methoxymethoxy)-2,5,9-trimethyl-3-oxotricyclo[6.3.0.0(2,6)]undec-4-en-6-yl]but-2-enoate
• CAS: 1370591-81-3
• 化学式: C₂₂H₃₂O₅
• 分子量: 376.493
• InChiKey: XJAAKKZAMUSDSJ-AHPWNQJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-4-[(1R,2S,6S,8R,9R,10S)-10-(methoxymethoxy)-2,5,9-trimethyl-3-oxotricyclo[6.3.0.0(2,6)]undec-4-en-6-yl]but-2-enoate 在 Wilkinson's catalyst 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 为溶剂， -70.0~20.0 ℃ 、101.33 kPa 条件下， 反应 30.67h， 生成 15-hydroxy-5-(methoxymethoxy)-12-epicrinipellin-9-one
  参考文献：
  名称：

  Enantiospecific total synthesis of 15-hydroxy-5-(methoxymethoxy)crinipellin-9-one

  摘要：

  Enantiospecific total synthesis of the crinipellin mentioned in the title was accomplished. In the present synthesis cyclopentane ring in campholenaldehyde was identified as the B-ring, two intramolecular rhodium carbenoid CH insertion reactions were employed for the construction of the A and C rings, and an intramolecular Michael addition reaction was utilized for the construction of the D-ring of crinipellin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.018
• 作为产物：
  描述：

  (1R,2S,6R,8R,9R,10S)-10-(methoxymethoxy)-2,9-dimethyltricyclo[6.3.0.0(2,6)]undec-3-en-5-one 在 重铬酸吡啶 、 sodium hydride 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 31.39h， 生成 ethyl (E)-4-[(1R,2S,6S,8R,9R,10S)-10-(methoxymethoxy)-2,5,9-trimethyl-3-oxotricyclo[6.3.0.0(2,6)]undec-4-en-6-yl]but-2-enoate
  参考文献：
  名称：

  Enantiospecific total synthesis of 15-hydroxy-5-(methoxymethoxy)crinipellin-9-one

  摘要：

  Enantiospecific total synthesis of the crinipellin mentioned in the title was accomplished. In the present synthesis cyclopentane ring in campholenaldehyde was identified as the B-ring, two intramolecular rhodium carbenoid CH insertion reactions were employed for the construction of the A and C rings, and an intramolecular Michael addition reaction was utilized for the construction of the D-ring of crinipellin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.018