(12R,16R)-5,7,14,21,23-pentaoxahexacyclo[16.7.0.02,10.04,8.012,16.020,24]pentacosa-1(25),2,4(8),9,18,20(24)-hexaene | 133494-55-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苯并环辛二烯木脂素
• 英文名称: (12R,16R)-5,7,14,21,23-pentaoxahexacyclo[16.7.0.02,10.04,8.012,16.020,24]pentacosa-1(25),2,4(8),9,18,20(24)-hexaene
• CAS: 133494-55-0
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: GROHUJPZGDJMCX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 三氟乙酸 为溶剂， 反应 2.0h， 以20%的产率得到(12R,16R)-5,7,14,21,23-pentaoxahexacyclo[16.7.0.02,10.04,8.012,16.020,24]pentacosa-1(25),2,4(8),9,18,20(24)-hexaene
  参考文献：
  名称：

  Oxidative transformations of lignans - reactions of dihydrocubebin and a derivative with DDQ

  摘要：

  Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound (8) and the aryl tetralin (9), while with DDQ in trifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.

  DOI：

  10.1016/s0040-4020(01)86384-5

文献信息

• Oxidative transformations of lignans - reactions of dihydrocubebin and a derivative with DDQ
  作者：Andrew Pelter、Robert S. Ward、Revuru Venkateswarlu、Chakicherla Kamakshi

  DOI：10.1016/s0040-4020(01)86384-5

  日期：1991.1

  Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound (8) and the aryl tetralin (9), while with DDQ in trifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.