endo-endo-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-dione | 179806-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: endo-endo-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-dione
• 英文别名: (1R,2R,3S,6R,7S,8S)-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.13,6.02,7]dodeca-4,9-diene
• CAS: 179806-40-7
• 化学式: C₁₃H₁₀Cl₆O
• 分子量: 394.94
• InChiKey: OPDJGCRBAMXVGZ-OBOWFAQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  endo-endo-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-dione 以 various solvent(s) 为溶剂， 生成 endo-exo-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-dione
  参考文献：
  名称：

  Kinetic and thermodynamic control in the formation of stereoisomeric 1:1 (4π+ 2π) thermal cycloadducts of furans with hexachloronorbornadienes

  摘要：

  The thermally, relatively stable, main product of the reaction of furan with dienophile 5a has been found to belong unambiguously to the endo-exo series of stereoisomeric adducts analogous to aldrin (endo-exo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene) 8. Also, the endo-endo isomeric adduct 16 has been found to comprise a minor component of the total products, In similar reactions of 2-methyl-, 2-ethyl- and 2,5-dimethyl-furan with Sa, it is shown that the respective endo-endo adducts 21, 23 and 25 are important reaction products and that the thermally unstable endo-endo adduct 25 predominates (greater than or equal to 6:1) over its endo-exo isomer 26 in the early phases of reaction, its abundance falling with heating time. The reactions of especially the alkylated furans with 5a provide useful sources of compounds ('oxaisodrins') having the skeletal features of isodrin endo-endo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene 1 otherwise not easily accessible.

  DOI：

  10.1039/p29960001233
• 作为产物：
  描述：

  2,5-二甲基呋喃 、 1,2,3,4,7,7-六氯双环[2.2.1]庚-2,5-二烯 生成 endo-endo-3,4,5,6,12,12-hexachloro-1,8-dimethyl-11-oxatetracyclo[6.2.1.1^3,6.0^2,7]dodeca-4,9-dione
  参考文献：
  名称：

  Kinetic and thermodynamic control in the formation of stereoisomeric 1:1 (4π+ 2π) thermal cycloadducts of furans with hexachloronorbornadienes

  摘要：

  The thermally, relatively stable, main product of the reaction of furan with dienophile 5a has been found to belong unambiguously to the endo-exo series of stereoisomeric adducts analogous to aldrin (endo-exo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene) 8. Also, the endo-endo isomeric adduct 16 has been found to comprise a minor component of the total products, In similar reactions of 2-methyl-, 2-ethyl- and 2,5-dimethyl-furan with Sa, it is shown that the respective endo-endo adducts 21, 23 and 25 are important reaction products and that the thermally unstable endo-endo adduct 25 predominates (greater than or equal to 6:1) over its endo-exo isomer 26 in the early phases of reaction, its abundance falling with heating time. The reactions of especially the alkylated furans with 5a provide useful sources of compounds ('oxaisodrins') having the skeletal features of isodrin endo-endo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene 1 otherwise not easily accessible.

  DOI：

  10.1039/p29960001233

文献信息

• Kinetic and thermodynamic control in the formation of stereoisomeric 1:1 (4π+ 2π) thermal cycloadducts of furans with hexachloronorbornadienes
  作者：Kenneth Mackenzie、Edward C. Gravett、Judith A. K. Howard、K. Brian Astin、Andrew M. Tomlins

  DOI：10.1039/p29960001233

  日期：——

  The thermally, relatively stable, main product of the reaction of furan with dienophile 5a has been found to belong unambiguously to the endo-exo series of stereoisomeric adducts analogous to aldrin (endo-exo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene) 8. Also, the endo-endo isomeric adduct 16 has been found to comprise a minor component of the total products, In similar reactions of 2-methyl-, 2-ethyl- and 2,5-dimethyl-furan with Sa, it is shown that the respective endo-endo adducts 21, 23 and 25 are important reaction products and that the thermally unstable endo-endo adduct 25 predominates (greater than or equal to 6:1) over its endo-exo isomer 26 in the early phases of reaction, its abundance falling with heating time. The reactions of especially the alkylated furans with 5a provide useful sources of compounds ('oxaisodrins') having the skeletal features of isodrin endo-endo-3,4,5,6,11,11-hexachlorotetracyclo[6.2.1.1(3.6).0(2.7)]dodeca-4,9-diene 1 otherwise not easily accessible.