5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-ol | 10059-66-2

• 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: 5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-ol
• 英文别名: 4-Monohydroxydihydroisodrin；(+/-)-1,8,9,10,11,11-hexachloro-endo-endo-tetracyclo[6.2.1.13,6.02,7]dodeca-9-en-4-exo-ol；(+/-)-1,8,9,10,11,11-hexachloro-endo-endo-tetracyclo[6.2.1.1^3,6.0^2,7]dodeca-9-en-4-exo-ol；5,6,7,8,9,9-Hexachlor-exo-2-hydroxy-1,2,3,4,4a,5,8,8a-octahydro-1,4-endo,endo-5,8-dimethanonaphthalin
• CAS: 10059-66-2；10059-67-3；10059-98-0；19711-30-9；33033-23-7；144787-47-3
• 化学式: C₁₂H₁₀Cl₆O
• 分子量: 382.929
• InChiKey: WFNWBCXXSCROFS-OQDWCBGHSA-N

物化性质

• 沸点：
  431.5±45.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-ol 在 lithium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以83%的产率得到(+/-)-endo-endo-tetracyclo[6.2.1.1^3,6.0^2,7]dodeca-9-en-4-exo-ol
  参考文献：
  名称：

  Study of the kinetic resolution of (±)-10-exo-hydroxy-pentacyclo[6.2.1.13,6.02,7.05,9]dodeca-4-one by lipase catalysis and the intramolecular racemization of the pure enantiomer by thermal dyotropic reaction

  摘要：

  In this work, the modified synthesis of (+/-)-10-exo-hydroxy-pentacyclo[6.2.1.1(3.6).0(2.7).0(5.9)]dodeca-4-one (+/-)-10 as well as its resolution by lipase-catalyzed transesterification with vinyl acetate is described. A thermal racernization process of (+)-10 to (+/-)-10 was observed. A mechanism involving racernization of (+/-)-10 through dyotropic intramolecular hydrogen migration is proposed and supported by computational analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00087-9
• 作为产物：
  描述：

  isodrin 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonaphthalen-2-ol
  参考文献：
  名称：

  Study of the kinetic resolution of (±)-10-exo-hydroxy-pentacyclo[6.2.1.13,6.02,7.05,9]dodeca-4-one by lipase catalysis and the intramolecular racemization of the pure enantiomer by thermal dyotropic reaction

  摘要：

  In this work, the modified synthesis of (+/-)-10-exo-hydroxy-pentacyclo[6.2.1.1(3.6).0(2.7).0(5.9)]dodeca-4-one (+/-)-10 as well as its resolution by lipase-catalyzed transesterification with vinyl acetate is described. A thermal racernization process of (+)-10 to (+/-)-10 was observed. A mechanism involving racernization of (+/-)-10 through dyotropic intramolecular hydrogen migration is proposed and supported by computational analysis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00087-9

文献信息

• Skeletal Rearrangements in Reactions of Isodrin and Endrin
  作者：S. B. Soloway、A. M. Damiana、J. W. Sims、H. Bluestone、R. E. Lidov

  DOI：10.1021/ja01505a024

  日期：1960.10