3-Diazonio-1-[4-(3-diazonio-2-oxidoindol-1-yl)butyl]indol-2-olate | 1173177-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-Diazonio-1-[4-(3-diazonio-2-oxidoindol-1-yl)butyl]indol-2-olate
• CAS: 1173177-78-0
• 化学式: C₂₀H₁₆N₆O₂
• 分子量: 372.386
• InChiKey: GBFBNBMGYAKGCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-丁二醇 、 3-Diazonio-1-[4-(3-diazonio-2-oxidoindol-1-yl)butyl]indol-2-olate 在 tetrakis(trifluoroacetato)rhodium(II) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以75%的产率得到(13S,20S)-14,19-dioxa-1,6-diazapentacyclo[18.6.1.16,13.07,12.021,26]octacosa-7,9,11,21,23,25-hexaene-27,28-dione
  参考文献：
  名称：

  环状铑类胡萝卜素的双OH插入反应：大环羟吲哚的非对映选择性合成

  摘要：

  在乙酸铑（II）催化剂存在下，环状重氮酰胺1和二羟基化合物2的双O-H插入反应已实现，最终导致了原型双（3-oxy-1,3-dihydro- 2 H -indol-2-one）系统。这种简便的双OH插入反应方案已成功地用于合成几个具有完全非对映选择性并带有羟吲哚单元的C 2对称大环。

  DOI：

  10.1016/j.tetlet.2009.04.035
• 作为产物：
  描述：

  1,4-二溴丁烷 、 3-diazo-indolin-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-Diazonio-1-[4-(3-diazonio-2-oxidoindol-1-yl)butyl]indol-2-olate
  参考文献：
  名称：

  Rhodium(II) catalyzed intermolecular double C-alkylation: a method for the synthesis of tetraindoles and indolophanes

  摘要：

  Double C-alkylation of cyclic diazoamides or bis-diazoamides with indoles or bis-indoles has been achieved to synthesize tetraindole derivatives using rhodium(II) acetate as a catalyst under mild reaction conditions with complete regioselectivity. The intermolecular double C-alkylation reaction strategy was successfully applied to synthesize indolophanes in moderate yield with excellent regiocontrol. The structure and stereochemistry of macrocycles were unequivocally confirmed with the help of single-crystal X-ray structure analyses. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.073

文献信息

• Blue LED-Mediated Synthesis of 3-Arylidene Oxindoles
  作者：Sengodagounder Muthusamy、Chinnathambi Ramesh

  DOI：10.1021/acs.joc.3c00099

  日期：2023.5.5

  Blue LED-promoted cross-coupling olefination of symmetrical and unsymmetrical 3-arylidene oxindoles has been described from diazoindolones and diphenylmethanethiones. Thermal olefin isomerization and stereoselective synthesis of 3-arylidene oxindoles were also demonstrated in good yield.

  蓝色 LED 促进的对称和不对称 3-亚芳基羟吲哚的交叉偶联烯化已从重氮吲哚酮和二苯基甲硫酮中得到描述。还证明了 3-亚芳基羟吲哚的热烯烃异构化和立体选择性合成具有良好的产率。
• Double O–H insertion reactions of cyclic rhodium carbenoids: diastereoselective synthesis of macrocyclic oxindoles
  作者：Sengodagounder Muthusamy、Pandurangan Srinivasan

  DOI：10.1016/j.tetlet.2009.04.035

  日期：2009.7

  Double O–H insertion reactions of cyclic diazo amides 1 and dihydroxy compounds 2 in the presence of rhodium(II) acetate catalyst have been achieved, which ultimately led to the facile synthesis of prototype bis(3-oxy-1,3-dihydro-2H-indol-2-one) systems. This facile double O–H insertion reaction protocol was successfully applied to synthesize several C2-symmetric macrocycles having oxindole units incorporated

  在乙酸铑（II）催化剂存在下，环状重氮酰胺1和二羟基化合物2的双O-H插入反应已实现，最终导致了原型双（3-oxy-1,3-dihydro- 2 H -indol-2-one）系统。这种简便的双OH插入反应方案已成功地用于合成几个具有完全非对映选择性并带有羟吲哚单元的C 2对称大环。
• Rhodium(II) catalyzed intermolecular double C-alkylation: a method for the synthesis of tetraindoles and indolophanes
  作者：Sengodagounder Muthusamy、Thangaraju Karikalan、Chidambaram Gunanathan、Eringathodi Suresh

  DOI：10.1016/j.tet.2011.11.073

  日期：2012.2

  Double C-alkylation of cyclic diazoamides or bis-diazoamides with indoles or bis-indoles has been achieved to synthesize tetraindole derivatives using rhodium(II) acetate as a catalyst under mild reaction conditions with complete regioselectivity. The intermolecular double C-alkylation reaction strategy was successfully applied to synthesize indolophanes in moderate yield with excellent regiocontrol. The structure and stereochemistry of macrocycles were unequivocally confirmed with the help of single-crystal X-ray structure analyses. (C) 2011 Elsevier Ltd. All rights reserved.