((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1aR,3aR,6aR,6bS)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxymethyl]-5,5,6b-trimethyl-3a,4,5,6,6a,6b-hexahydro-1H-cyclopropa[e]inden-1a-ylmethyl ester | 196501-16-3

• 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: ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1aR,3aR,6aR,6bS)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxymethyl]-5,5,6b-trimethyl-3a,4,5,6,6a,6b-hexahydro-1H-cyclopropa[e]inden-1a-ylmethyl ester
• CAS: 196501-16-3
• 化学式: C₃₉H₆₄O₆
• 分子量: 628.934
• InChiKey: XVVKFWVCXXCQEE-CKWOUFBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1aR,3aR,6aR,6bS)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxymethyl]-5,5,6b-trimethyl-3a,4,5,6,6a,6b-hexahydro-1H-cyclopropa[e]inden-1a-ylmethyl ester 在 氢氧化钾 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Isovelleral
  参考文献：
  名称：

  The preparation and bioactivities of (−)-isovelleral1,2

  摘要：

  The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00055-2
• 作为产物：
  描述：

  氧基乙酰氯 、 (1aα,3aβ,6aβ,6bα)-(+/-)-3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethylcyclopropindene-1a,2(1H)-dimethanol 在 吡啶 作用下， 反应 2.0h， 以70 mg的产率得到((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (1aS,3aS,6aS,6bR)-2-[2-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-acetoxymethyl]-5,5,6b-trimethyl-3a,4,5,6,6a,6b-hexahydro-1H-cyclopropa[e]inden-1a-ylmethyl ester
  参考文献：
  名称：

  The preparation and bioactivities of (−)-isovelleral1,2

  摘要：

  The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00055-2