(2R,2'R)-2,2'-biindoline | 1239600-44-2

• 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: (2R,2'R)-2,2'-biindoline
• 英文别名: (2R,2'R)-biindoline；(2R,2'R)-2,2'-Biindoline；(2R)-2-[(2R)-2,3-dihydro-1H-indol-2-yl]-2,3-dihydro-1H-indole
• CAS: 1239600-44-2
• 化学式: C₁₆H₁₆N₂
• 分子量: 236.316
• InChiKey: VTRXPGMEDRKZSJ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  di-tert-butyl (2R,2'R)-[2,2'-biindoline]-1,1'-dicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(2R,2'R)-2,2'-biindoline
  参考文献：
  名称：

  The attempted stereoselective synthesis of chiral 2,2′-biindoline

  摘要：

  The attempted first stereoselective synthesis of 2,2'-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.035

文献信息

• Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
  作者：Stephen J. Bailey、Steven M. Wales、Anthony C. Willis、Paul A. Keller

  DOI：10.1021/ol502164b

  日期：2014.8.15

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.
• The attempted stereoselective synthesis of chiral 2,2′-biindoline
  作者：Mary J. Gresser、Steven M. Wales、Paul A. Keller

  DOI：10.1016/j.tet.2010.06.035

  日期：2010.8

  The attempted first stereoselective synthesis of 2,2'-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the heteroatom protecting groups in key intermediates did not enhance the outcome of the Sharpless AD reaction. Therefore a limitation of this AD reaction is the use of 1,4-substituted but-2-enes where these substituents are ortho-substituted aromatics. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.