6,13-bisdiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone | 951390-69-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6,13-bisdiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone
• 英文别名: 6,13-Didiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetrone；6,13-didiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetrone
• CAS: 951390-69-5
• 化学式: C₁₀H₈N₄O₈
• 分子量: 312.196
• InChiKey: TZDUAMYQZSJODY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6,13-bisdiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone 、 1-苄基吲哚 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以50%的产率得到6,13-bis-(1-benzyl-1H-indol-3-yl)-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone
  参考文献：
  名称：

  Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands

  摘要：

  A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(H) carberioid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carberioid insertion was also performed to afford indolyl cryptand molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.102
• 作为产物：
  描述：

  1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到6,13-bisdiazo-1,4,8,11-tetraoxacyclotetradecane-5,7,12,14-tetraone
  参考文献：
  名称：

  Reactions of macrocyclic rhodium carbenoids: regioselective synthesis of indol-3-yl macrocyclic lactones and cryptands

  摘要：

  A wide variety of new macrocyclic diazocarbonyl compounds with various spacers was synthesized. Macrocyclic rhodium(H) carberioid insertion with various substituted indoles was performed to afford regioselectively, indol-3-yl macrocyclic di- or tetralactones (C3-alkylation). Double carberioid insertion was also performed to afford indolyl cryptand molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.102

文献信息

• Insertion reactions of macrocyclic rhodium carbenoids: a novel method for the synthesis of cryptands
  作者：Sengodagounder Muthusamy、Boopathy Gnanaprakasam

  DOI：10.1016/j.tetlet.2007.07.035

  日期：2007.9

  Reaction of macrocyclic diazocarbonyl compounds and alcohols or diols in the presence of rhodium(II) acetate catalyst led to functionalized macrocyclic di- or tetralactones via O–H insertion. Interestingly, the double O–H insertion reaction with dihydroxy compounds gave cryptands of various ring sizes.

  在乙酸铑（II）催化剂存在下，大环重氮羰基化合物与醇或二醇的反应通过OH插入导致官能化的大环二或四内酯。有趣的是，双羟基化合物与二羟基化合物的双重插入反应产生了各种环大小的穴状分子。