(4aS,8aS)-5,5,8a-trimethyl-6-methyleneoctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolane] | 218453-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aS)-5,5,8a-trimethyl-6-methyleneoctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolane]
• CAS: 218453-43-1
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: QLMUEMVGQSPCEL-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4aS,8aS)-5,5,8a-trimethyl-6-methyleneoctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolane] 在 铂 氢气 作用下， 以 甲醇 为溶剂， 以11%的产率得到
  参考文献：
  名称：

  An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate

  摘要：

  A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00349-8
• 作为产物：
  描述：

  2-methyl-2-(3-oxopentyl)-1,3-cyclohexanedione 在 正丁基锂 、 L-苯丙氨酸 、 氨 、 草酸 、 lithium 、 (+)-10-camphorsulfonic acid 作用下， 以 苯 为溶剂， 生成 (4aS,8aS)-5,5,8a-trimethyl-6-methyleneoctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolane]
  参考文献：
  名称：

  An investigation into the total synthesis of clerocidin: stereoselective synthesis of a clerodane intermediate

  摘要：

  A key clerodane intermediate was prepared during the investigation of the total synthesis of clerocidin. The diterpene backbone was synthesized by an enantioselective Robinson annulation followed by trapping of the enolate using allyl bromide. Selective hydrogenation conditions were developed to introduce the axial methyl group at the C-8 position. A palladium-mediated carbonylation reaction was employed to generate the key alpha,beta-unsaturated dialdehyde. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00349-8