5-(1-benzyl-2-chloro-1H-indol-3-yl)-2-(benzyloxy)pentanenitrile | 1254982-28-9

• 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: 5-(1-benzyl-2-chloro-1H-indol-3-yl)-2-(benzyloxy)pentanenitrile
• 英文别名: 5-(1-Benzyl-2-chloroindol-3-yl)-2-phenylmethoxypentanenitrile
• CAS: 1254982-28-9
• 化学式: C₂₇H₂₅ClN₂O
• 分子量: 428.961
• InChiKey: UHQWMTHHDQDXNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-benzyl-2-chloro-1H-indol-3-yl)-2-(benzyloxy)pentanenitrile 在 sodium tetrahydroborate 、 Schwartz's reagent 、 palladium 10% on activated carbon 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 16.75h， 生成 N-(1'-benzyl-3-hydroxy-2'-oxospiro[cyclohexane-1,3'-indoline]-2-yl)-3-phenylpropanamide
  参考文献：
  名称：

  Construction of a Spirooxindole Amide Library through Nitrile Hydrozirconation-Acylation-Cyclization Cascade

  摘要：

  A library of spirooxindoles containing varied elements of structural and stereochemical diversity has been constructed via a three step, one pot nitrile hydrozirconation-acylation-cyclization reaction sequence from common acyclic indole intermediates. The resulting library was evaluated for novelty through comparison with MLSMR and Maybridge compound collections.

  DOI：

  10.1021/co4000387
• 作为产物：
  描述：

  苄氧基三甲基硅烷 在 N-氯代丁二酰亚胺 、 bismuth(III) bromide 、 臭氧 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 5-(1-benzyl-2-chloro-1H-indol-3-yl)-2-(benzyloxy)pentanenitrile
  参考文献：
  名称：

  Construction of a Spirooxindole Amide Library through Nitrile Hydrozirconation-Acylation-Cyclization Cascade

  摘要：

  A library of spirooxindoles containing varied elements of structural and stereochemical diversity has been constructed via a three step, one pot nitrile hydrozirconation-acylation-cyclization reaction sequence from common acyclic indole intermediates. The resulting library was evaluated for novelty through comparison with MLSMR and Maybridge compound collections.

  DOI：

  10.1021/co4000387

文献信息

• Stereoselective Synthesis of Spirooxindole Amides through Nitrile Hydrozirconation
  作者：Chunliang Lu、Qing Xiao、Paul E. Floreancig

  DOI：10.1021/ol102246d

  日期：2010.11.19

  Spirooxindole amides can be prepared by the intramolecular addition of functionalized indoles into acylimines that are accessed from nitriles by hydrozirconation and acylation. The stereochemical outcome at the quaternary center was controlled by the steric bulk of the substituent at the 2-position of the indole unit. The products are well-suited for diversification to prepare libraries.
• Construction of a Spirooxindole Amide Library through Nitrile Hydrozirconation-Acylation-Cyclization Cascade
  作者：Matthew G. LaPorte、Sammi Tsegay、Ki Bum Hong、Chunliang Lu、Cheng Fang、Lirong Wang、Xiang-Qun Xie、Paul E. Floreancig

  DOI：10.1021/co4000387

  日期：2013.7.8

  A library of spirooxindoles containing varied elements of structural and stereochemical diversity has been constructed via a three step, one pot nitrile hydrozirconation-acylation-cyclization reaction sequence from common acyclic indole intermediates. The resulting library was evaluated for novelty through comparison with MLSMR and Maybridge compound collections.