(1R,2S,6R,8R,9R,10S)-10-(methoxymethoxy)-2,9-dimethyltricyclo[6.3.0.0(2,6)]undec-3-en-5-one | 1370591-13-1

• 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: (1R,2S,6R,8R,9R,10S)-10-(methoxymethoxy)-2,9-dimethyltricyclo[6.3.0.0(2,6)]undec-3-en-5-one
• 英文别名: (3aS,3bR,5S,6R,6aR,7aR)-5-(methoxymethoxy)-3a,6-dimethyl-4,5,6,6a,7,7a-hexahydro-3bH-cyclopenta[a]pentalen-1-one
• CAS: 1370591-13-1
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: SYFRNBQGJQQQSN-PWCLGXPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 Wilkinson's catalyst 、 重铬酸吡啶 、 氢气 、 sodium hydride 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -70.0~20.0 ℃ 、101.33 kPa 条件下， 反应 62.06h， 生成 15-hydroxy-5-(methoxymethoxy)crinipellin-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：

  (1S,2R,4S,5R,6R,8R)-1,5-dimethyl-9-oxotricyclo[6.3.0.0(2,6)]undec-10-en-4-yl benzoate 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (1R,2S,6R,8R,9R,10S)-10-(methoxymethoxy)-2,9-dimethyltricyclo[6.3.0.0(2,6)]undec-3-en-5-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

文献信息

• Enantiospecific total synthesis of 15-hydroxy-5-(methoxymethoxy)crinipellin-9-one
  作者：A. Srikrishna、V. Gowri

  DOI：10.1016/j.tet.2012.02.018

  日期：2012.4

  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.