16,19-dimethoxy-heptacyclo-1α,2β,4β,5α,8α,9β,11β,12α-[10.10.1.1^5,8.0^2,11.0^3,10.0^4,9]tetracosa-6,12,15,17,19,21-hexaene-3,10-dicarbonyl chloride | 1448550-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 16,19-dimethoxy-heptacyclo-1α,2β,4β,5α,8α,9β,11β,12α-[10.10.1.1^5,8.0^2,11.0^3,10.0^4,9]tetracosa-6,12,15,17,19,21-hexaene-3,10-dicarbonyl chloride
• CAS: 1448550-92-2
• 化学式: C₂₈H₂₄Cl₂O₄
• 分子量: 495.402
• InChiKey: DEQHIJPEUGUASF-SZKRCHNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  16,19-dimethoxy-heptacyclo-1α,2β,4β,5α,8α,9β,11β,12α-[10.10.1.1^5,8.0^2,11.0^3,10.0^4,9]tetracosa-6,12,15,17,19,21-hexaene-3,10-dicarbonyl chloride 、 sodium methylate 以 甲醇 为溶剂， 反应 16.0h， 以91%的产率得到dimethyl-(1α,4α,4aβ,4bα,4cβ,5α,12α,12aβ,12bα,12cβ)-1,4,4a,4c,5,12,12a,12c-octahydro-1,4:5, 12-dimethano-6,11-dimethoxybenzo(3',4')cyclobuta(1',2':3,4)cyclobut(1,2-b)anthracene-4b,12b,dicarboxylate
  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：

  3,10-dimethoxy-1α,12α,13β,16β-pentacyclo[10.4.1.0^2,11.0^4,9.0^13,16]heptadeca-2,4,6,8,10,14-hexaen-14,15-dicarboxylic acid chloride 、 Quadricyclane 以 氯仿 为溶剂， 反应 0.5h， 以93%的产率得到16,19-dimethoxy-heptacyclo-1α,2β,4β,5α,8α,9β,11β,12α-[10.10.1.1^5,8.0^2,11.0^3,10.0^4,9]tetracosa-6,12,15,17,19,21-hexaene-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