isoplagiochin C | 1438417-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: isoplagiochin C
• 英文别名: Pentacyclo[20.2.2.110,14.115,19.02,7]octacosa-1(24),2(7),3,5,10(28),11,13,15,17,19(27),20,22,25-tridecaene-5,13,16,24-tetrol；pentacyclo[20.2.2.110,14.115,19.02,7]octacosa-1(24),2(7),3,5,10(28),11,13,15,17,19(27),20,22,25-tridecaene-5,13,16,24-tetrol
• CAS: 1438417-03-8；159194-79-3
• 化学式: C₂₈H₂₂O₄
• 分子量: 422.48
• InChiKey: AANIEYOTXCALEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-2,2'-Binaphthyldicarboxylic acid dichloride 、 isoplagiochin C 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 37,42-dihydroxy-5,28-dioxadecacyclo[30.14.4.235,38.04,48.07,16.010,15.017,26.018,23.029,49.039,44]dopentaconta-1(47),2,4(48),7(16),8,10,12,14,17(26),18,20,22,24,29(49),30,32(50),33,35,37,39(44),40,42,51-tricosaene-6,27-dione
  参考文献：
  名称：

  Enantiopure isoplagiochin C by directed deracemization through axis-to-axis chirality transfer

  摘要：

  Isoplagiochin C 1 was prepared for the first time in an enantiopure form from synthetic racemic material, using a novel stereochemical concept. This macrocyclic bisbibenzyl contains two biaryl axes. Of these, axis A is configurationally stable by its fixation within the macrocyclic framework, while axis B is stereochemically unstable. By diesterification of rac-1 with enantiopure (P)-1,1'-binaphthyl-2,2'-dicarboxylic acid, axis B is locked in its P-configuration, thus allowing the resolution and separate saponification of dilactones (P-A,P-B,P)-3 and (M-A,P-B,P)-3 to give the pure enantiomers of 1. This concept permits recycling of any undesired enantiomer of 1 by thermal equilibration of the respective diastereomer of 3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.012
• 作为产物：
  描述：

  甲醇 、 37,42-dihydroxy-5,28-dioxadecacyclo[30.14.4.235,38.04,48.07,16.010,15.017,26.018,23.029,49.039,44]dopentaconta-1(47),2,4(48),7(16),8,10,12,14,17(26),18,20,22,24,29(49),30,32(50),33,35,37,39(44),40,42,51-tricosaene-6,27-dione 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以100%的产率得到isoplagiochin C
  参考文献：
  名称：

  Enantiopure isoplagiochin C by directed deracemization through axis-to-axis chirality transfer

  摘要：

  Isoplagiochin C 1 was prepared for the first time in an enantiopure form from synthetic racemic material, using a novel stereochemical concept. This macrocyclic bisbibenzyl contains two biaryl axes. Of these, axis A is configurationally stable by its fixation within the macrocyclic framework, while axis B is stereochemically unstable. By diesterification of rac-1 with enantiopure (P)-1,1'-binaphthyl-2,2'-dicarboxylic acid, axis B is locked in its P-configuration, thus allowing the resolution and separate saponification of dilactones (P-A,P-B,P)-3 and (M-A,P-B,P)-3 to give the pure enantiomers of 1. This concept permits recycling of any undesired enantiomer of 1 by thermal equilibration of the respective diastereomer of 3. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.012