methyl (1R,3aS,6aR)-6a-(2-dimethoxyphosphorylacetyl)-1-methyl-1,2,3,4,5,6-hexahydropentalene-3a-carboxylate | 133627-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: methyl (1R,3aS,6aR)-6a-(2-dimethoxyphosphorylacetyl)-1-methyl-1,2,3,4,5,6-hexahydropentalene-3a-carboxylate
• CAS: 133627-60-8
• 化学式: C₁₅H₂₅O₆P
• 分子量: 332.334
• InChiKey: IALDKPUTSOASJK-DFBGVHRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (1R,3aS,6aR)-6a-(2-dimethoxyphosphorylacetyl)-1-methyl-1,2,3,4,5,6-hexahydropentalene-3a-carboxylate 在 Crabtree catalyst 、 18-冠醚-6 氢气 、 potassium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 4,6-dimethyltricyclo<3.3.3.0>undec-3-en-2-one
  参考文献：
  名称：

  Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene

  摘要：

  A synthesis of modhephene has been achieved, the key feature of which is the use of a novel nucleophilic addition/rearrangement reaction to develop the carbon framework. Stereochemical control of the stereogenic center bearing the methyl group was accomplished by variation of the hydrogenation conditions. As a byproduct of this work, we have clarified structural assignments of intermediates from previous syntheses.

  DOI：

  10.1021/jo00013a014
• 作为产物：
  描述：

  2-bromo-6-(methoxycarbonyl)-cyclohexanone 在 palladium on activated charcoal 正丁基锂 、 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 109.5h， 生成 methyl (1R,3aS,6aR)-6a-(2-dimethoxyphosphorylacetyl)-1-methyl-1,2,3,4,5,6-hexahydropentalene-3a-carboxylate
  参考文献：
  名称：

  Reactions of bridgehead halides. A synthesis of modhephene, isomodhephene, and epi-modhephene

  摘要：

  A synthesis of modhephene has been achieved, the key feature of which is the use of a novel nucleophilic addition/rearrangement reaction to develop the carbon framework. Stereochemical control of the stereogenic center bearing the methyl group was accomplished by variation of the hydrogenation conditions. As a byproduct of this work, we have clarified structural assignments of intermediates from previous syntheses.

  DOI：

  10.1021/jo00013a014

文献信息

• Rearrangements of bridgehead bromides. A direct synthesis of epi-modhephene
  作者：George A. Kraus、Jianmin Shi

  DOI：10.1021/jo00307a001

  日期：1990.9
• KRAUS, GEORGE A.;SHI, JIANMIN, J. ORG. CHEM., 56,(1991) N3, C. 4147-4151
  作者：KRAUS, GEORGE A.、SHI, JIANMIN

  DOI：——

  日期：——