(3aR,5aR,9aS)-3a-Methyl-8-oxo-2,3,3a,4,5,8,9,9a-octahydro-cyclopenta[a]naphthalene-5a-carboxylic acid methyl ester | 467242-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5aR,9aS)-3a-Methyl-8-oxo-2,3,3a,4,5,8,9,9a-octahydro-cyclopenta[a]naphthalene-5a-carboxylic acid methyl ester
• 英文别名: methyl (3aR,5aR,9aS)-3a-methyl-8-oxo-2,3,4,5,9,9a-hexahydrocyclopenta[a]naphthalene-5a-carboxylate
• CAS: 467242-45-1
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: SVZOEUCRXCJSEN-IMJJTQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,5aR,9aS)-3a-Methyl-8-oxo-2,3,3a,4,5,8,9,9a-octahydro-cyclopenta[a]naphthalene-5a-carboxylic acid methyl ester 在 sodium hydroxide 、 sodium tetrahydroborate 、 4 A molecular sieve 、 二苯基二硒醚 、 双氧水 、 sodium acetate 、 lithium 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氨 、 叔丁醇 为溶剂， 反应 15.0h， 生成 (3aR,5aR,9aS)-3a-Methyl-8-oxo-2,3,3a,4,5,6,7,8,9,9a-decahydro-cyclopenta[a]naphthalene-5a-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization

  摘要：

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00570-1
• 作为产物：
  描述：

  methyl (3aR,5aR,8R,9aS)-8-acetyloxy-3a-methyl-3,4,5,8,9,9a-hexahydro-2H-cyclopenta[a]naphthalene-5a-carboxylate 在 manganese(IV) oxide 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 (3aR,5aR,9aS)-3a-Methyl-8-oxo-2,3,3a,4,5,8,9,9a-octahydro-cyclopenta[a]naphthalene-5a-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization

  摘要：

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00570-1

文献信息

• Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization
  作者：Cyrille Thominiaux、Angèle Chiaroni、Didier Desmaële

  DOI：10.1016/s0040-4039(02)00570-1

  日期：2002.5

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.