(4aS,8aS)-8-[(Z)-2-((1aR,3aS,5S,7aS,7bS)-5-Hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester | 700841-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (4aS,8aS)-8-[(Z)-2-((1aR,3aS,5S,7aS,7bS)-5-Hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester
• 英文别名: methyl (4aS,8aS)-8-[(Z)-2-[(1aR,3aS,5S,7aS,7bS)-5-hydroxy-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]ethenyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydronaphthalene-4a-carboxylate
• CAS: 700841-24-3
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: OTMIPNRAXOJAAJ-KPKCCSSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aS,8aS)-8-[(Z)-2-((1aR,3aS,5S,7aS,7bS)-5-Hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以60%的产率得到(1S,2S,4aS,8aR)-1,2-Dihydroxy-1-[(Z)-2-((1aR,3aS,5S,7aS,7bS)-5-hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-vinyl]-2,7,7-trimethyl-octahydro-naphthalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis

  摘要：

  An exhaustive oxidation study has been made with ozone, MCPBA and/or NaIO4/RuCl3 of several triterpenic diene and triene compounds from oleanolic and maslinic acids obtained from olive-oil pressing. Through several oxidative cleavages of the opened C-ring of these oleantrienes, different significant decalin-type chiral synthons were achieved. These sesquiterpene and nor-sesquiterpene products are of great interest because by means of several simple reactions they could lead to drimane, phenanthrene and tricyclic triterpene compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.008
• 作为产物：
  描述：

  (4aS,8aS)-8-[(Z)-2-((4aR,6S,8aS)-6-Hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到(4aS,8aS)-8-[(Z)-2-((1aR,3aS,5S,7aS,7bS)-5-Hydroxy-1a,4,4,7a-tetramethyl-octahydro-1-oxa-cyclopropa[a]naphthalen-7b-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis

  摘要：

  An exhaustive oxidation study has been made with ozone, MCPBA and/or NaIO4/RuCl3 of several triterpenic diene and triene compounds from oleanolic and maslinic acids obtained from olive-oil pressing. Through several oxidative cleavages of the opened C-ring of these oleantrienes, different significant decalin-type chiral synthons were achieved. These sesquiterpene and nor-sesquiterpene products are of great interest because by means of several simple reactions they could lead to drimane, phenanthrene and tricyclic triterpene compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.008