2-((1aS,4aS,7R,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-7-yl)-propan-2-ol | 210291-06-8

• 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: 2-((1aS,4aS,7R,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-7-yl)-propan-2-ol
• 英文别名: 2-[(1aS,4aS,7R,8aR)-1a,4a-dimethyl-3,4,5,6,7,8-hexahydro-2H-naphtho[1,8a-b]oxiren-7-yl]propan-2-ol
• CAS: 210291-06-8
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: ZGMFFZYUZKZDRL-UQOMUDLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((1aS,4aS,7R,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-7-yl)-propan-2-ol 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以69%的产率得到(4β,5β,7β,10α)-5,11-eudesmanediol
  参考文献：
  名称：

  An efficient stereocontrolled synthesis of (−)-10-epi-5β,11-dihydroxyeudesmane and (−)-4,10-epi-5β,11-dihydroxyeudesmane

  摘要：

  A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeudesmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10-epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvone. The salient feature of our synthesis is the utilization of substrate-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00141-4
• 作为产物：
  描述：

  7-epi-cyperone 在 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 bis(acetylacetonate)oxovanadium 、 dichloroalane 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 25.0h， 生成 2-((1aS,4aS,7R,8aR)-1a,4a-Dimethyl-octahydro-1-oxa-cyclopropa[d]naphthalen-7-yl)-propan-2-ol
  参考文献：
  名称：

  An efficient stereocontrolled synthesis of (−)-10-epi-5β,11-dihydroxyeudesmane and (−)-4,10-epi-5β,11-dihydroxyeudesmane

  摘要：

  A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeudesmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10-epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvone. The salient feature of our synthesis is the utilization of substrate-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00141-4

文献信息

• An efficient stereocontrolled synthesis of (−)-10-epi-5β,11-dihydroxyeudesmane and (−)-4,10-epi-5β,11-dihydroxyeudesmane
  作者：Zhaoming Xiong、Gang Zhou、Jiong Yang、Yonggang Chen、Yulin Li

  DOI：10.1016/s0957-4166(98)00141-4

  日期：1998.5

  A concise and efficient synthesis of (-)-10-epi-5 beta, 11-dihydroxyeudesmane 1 and (-)-4,10-epi-5 beta, 11-dihydroxyeudesmane 2, via (-)-10-epi-gamma-eudesmol 5, was accomplished starting from (+)-dihydrocarvone. The salient feature of our synthesis is the utilization of substrate-directable epoxidation and homogeneous hydrogenation to control the stereochemistry at the C-4 and C-5 positions of the title compounds. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.