<3R-(3α,3aα,5aS,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3-hydroxy-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid methyl ester | 138750-66-0

• 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: <3R-(3α,3aα,5aS,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3-hydroxy-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,4S,9S,10R,13R,14S)-13-hydroxy-5,5,9-trimethyltetracyclo[8.6.0.01,14.04,9]hexadec-15-ene-13-carboxylate
• CAS: 138750-66-0
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: CSILRVZTERMEJQ-PXUMCECISA-N

物化性质

• 沸点：
  410.1±45.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  <3R-(3α,3aα,5aS,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3-hydroxy-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid methyl ester 在 六甲基磷酰三胺 、 氢氧化钾 、 samarium diiodide 、 三甲基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 72.25h， 生成 <3R-(3β,3aα,5aR,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid
  参考文献：
  名称：

  Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1

  摘要：

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.

  DOI：

  10.1021/jo00051a035
• 作为产物：
  描述：

  Δ⁸⁽¹⁴⁾-podocarpen-13-one 在 sodium methylate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 丙酮 为溶剂， 反应 4.75h， 生成 <3R-(3α,3aα,5aS,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-3-hydroxy-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Spongian pentacyclic diterpenes. Stereoselective synthesis of (-)-dendrillol-1

  摘要：

  A formal total synthesis of the spongian diterpene (-)-dendrillol-1 (3), through a consice approach that could be used for the synthesis of other pentacyclic spongian diterpenes, is reported. The synthesis is based on the intramolecular acetalization of an acid-dialdehyde 4, which is prepared from (+)-podocarp-8(14)-en-13-one (5) via a sequence of transformations involving (a) introduction of a latent dialdehyde unit on 5 by photochemical reaction with acetylene, (b) reductive carboxylation at C-13 of photoadduct 6 to obtain acid 18, and (c) elaboration of the dialdehyde moiety at C-8 and C-14 of 18 by ozonolysis. Several procedures that have been examined for the reductive carboxylation at C-13 of 6 are described. A simple three-step procedure to effect the conversion of a podocarp-8-en-13-one system into a C-17-functionalized beyerane compound is also reported.

  DOI：

  10.1021/jo00051a035