1α,2β,4β,5α,8α,9β,11β,12α-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarbonyl chloride | 1448550-87-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1α,2β,4β,5α,8α,9β,11β,12α-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarbonyl chloride
• 英文别名: 1α,2β,4β,5α,8α,9β,11β,12α-hexacyclo[10.2.1.1^5,8.0^2,11.0^3,10.0^4,9]hexadeca-6,13-diene-3,10-dicarbonyl chloride
• CAS: 1448550-87-5
• 化学式: C₁₈H₁₆Cl₂O₂
• 分子量: 335.23
• InChiKey: RRXJOVZNFLXLPP-MMFFIYSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1α,2β,4β,5α,8α,9β,11β,12α-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarbonyl chloride 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 14.0h， 以86%的产率得到1α,2β,4β,5α,8α,9β,11β,12α-Hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarboxylic acid
  参考文献：
  名称：

  Reactivity increase of dienophiles by change of the ester substituents into the acid chlorides: cycloaddition reaction of the diacid chloride of 3,10-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarboxylic acid with quadricyclane

  摘要：

  Conversion of the ester substituents on the cyclobutene it-bond of dimethyl tricyclo[4.2.1.0(2,5)]nona-3,7-diene-3,4-dicarboxylate to the corresponding acid chloride increases the cycloaddition reactivity toward quadricyclane so dramatically that the reaction temperature can be dropped from 180 degrees C (preparation of title 3,10-diester) to room temperature (preparation of the title 3,10-diacid chloride). The cycloadduct product, an acid chloride of the title ring system, is extremely docile and can be recrystallized unchanged from hot methanol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.057
• 作为产物：
  描述：

  二甲基(1R,2R,5S,6S)-三环[4.2.1.02,5]壬-3,7-二烯-3,4-二羧酸酯 在 氯化亚砜 、 potassium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 21.0h， 生成 1α,2β,4β,5α,8α,9β,11β,12α-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarbonyl chloride
  参考文献：
  名称：

  Reactivity increase of dienophiles by change of the ester substituents into the acid chlorides: cycloaddition reaction of the diacid chloride of 3,10-hexacyclo[10.2.1.15,8.02,11.03,10.04,9]hexadeca-6,13-diene-3,10-dicarboxylic acid with quadricyclane

  摘要：

  Conversion of the ester substituents on the cyclobutene it-bond of dimethyl tricyclo[4.2.1.0(2,5)]nona-3,7-diene-3,4-dicarboxylate to the corresponding acid chloride increases the cycloaddition reactivity toward quadricyclane so dramatically that the reaction temperature can be dropped from 180 degrees C (preparation of title 3,10-diester) to room temperature (preparation of the title 3,10-diacid chloride). The cycloadduct product, an acid chloride of the title ring system, is extremely docile and can be recrystallized unchanged from hot methanol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.057