(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 | 676248-25-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (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
• 英文别名: methyl (4aS,8aS)-8-[(Z)-2-[(4aR,6S,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethenyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydronaphthalene-4a-carboxylate
• CAS: 676248-25-2
• 化学式: C₃₁H₄₈O₃
• 分子量: 468.72
• InChiKey: DMIJROGEXHZPRT-NNCZMWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 碘 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以60%的产率得到(4aS,8aS)-8-[(E)-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
  参考文献：
  名称：

  由齐墩果酸和山梨酸部分合成C环衍生物。通过化学和光化学异构化过程形成数个三烯系统

  摘要：

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。

  DOI：

  10.1016/j.tet.2003.12.023
• 作为产物：
  描述：

  methyl 3β-hydroxyoleana-9(11),12-dien-28-oate 以 乙醇 为溶剂， 反应 0.33h， 以95%的产率得到(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
  参考文献：
  名称：

  由齐墩果酸和山梨酸部分合成C环衍生物。通过化学和光化学异构化过程形成数个三烯系统

  摘要：

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。

  DOI：

  10.1016/j.tet.2003.12.023

文献信息

• Oxidation of several triterpenic diene and triene systems. Oxidative cleavage to obtain chiral intermediates for drimane and phenanthrene semi-synthesis
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2004.03.008

  日期：2004.4

  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.
• Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2003.12.023

  日期：2004.2

  Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。