methyl (2R,3aS,5aS,9aR,9bS)-2,9b-dihydroxy-3a,8,8-trimethyl-1,2,4,5,6,7,9,9a-octahydrobenzo[e][1]benzofuran-5a-carboxylate | 700841-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2R,3aS,5aS,9aR,9bS)-2,9b-dihydroxy-3a,8,8-trimethyl-1,2,4,5,6,7,9,9a-octahydrobenzo[e][1]benzofuran-5a-carboxylate
• CAS: 700841-47-0
• 化学式: C₁₇H₂₈O₅
• 分子量: 312.406
• InChiKey: KXWCYWXWVFVPAJ-XYFLEOOXSA-N

物化性质

• 沸点：
  417.9±45.0 °C(predicted)
• 密度：
  1.210±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R,3aS,5aS,9aR,9bS)-2,9b-dihydroxy-3a,8,8-trimethyl-1,2,4,5,6,7,9,9a-octahydrobenzo[e][1]benzofuran-5a-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(1S,2S,4aS,8aR)-1-(2-hydroxyethyl)-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalene-1,2-diol
  参考文献：
  名称：

  Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

  摘要：

  Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive-oil pressing, was fragmented through the C-ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis-decalin, from the D and E rings, and of trans-decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene- and drimane-type compounds and natural tricyclic triterpenes.

  DOI：

  10.1080/00397910600773858
• 作为产物：
  描述：

  (1aS,3aS,7aR,7bR)-7b-{2-[(4aR,6R,7R,8aS)-6,7-Diacetoxy-5,5,8a-trimethyl-2-methylene-octahydro-naphthalen-(1E)-ylidene]-ethyl}-1a,6,6-trimethyl-octahydro-1-oxa-cyclopropa[a]naphthalene-3a-carboxylic acid methyl ester 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 36.08h， 以35%的产率得到methyl (2R,3aS,5aS,9aR,9bS)-2,9b-dihydroxy-3a,8,8-trimethyl-1,2,4,5,6,7,9,9a-octahydrobenzo[e][1]benzofuran-5a-carboxylate
  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