(4R)-1'-methylspiro[cyclohexene-4,3'-indole]-2'-one | 109686-71-7

• 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: (4R)-1'-methylspiro[cyclohexene-4,3'-indole]-2'-one
• CAS: 109686-71-7
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: OKRSAJFQPSCGJW-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-iodophenyl)-N-methyl-1-cyclohexene-1-carboxamide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 1,2,2,6,6-五甲基哌啶 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 (4R)-1'-methylspiro[cyclohexene-4,3'-indole]-2'-one 、 (3S)-1'-methylspiro[cyclohexene-3,3'-indole]-2'-one 、 (3R)-1'-methylspiro[cyclohexene-3,3'-indole]-2'-one
  参考文献：
  名称：

  Catalytic asymmetric synthesis of quarternary carbon centers. Palladium-catalyzed formation of either enantiomer of spirooxindoles and related spirocyclics using a single enantiomer of a chiral diphosphine ligand

  摘要：

  The asymmetric synthesis of eight spirooxindoles and related spirocyclics from the corresponding aryl iodide by palladium catalyzed cyclizations in the presence of the diphosphine ligand (R)-(+)-BINAP is reported.

  DOI：

  10.1021/jo00043a005

文献信息

• Applications of 3,3′-Disubstituted BINAP Derivatives in Inter- and Intramolecular Heck/Mizoroki Reactions
  作者：Brian Keay、J. Hopkins、Evgueni Gorobets、Bronwen Wheatley、Masood Parvez

  DOI：10.1055/s-2006-950404

  日期：2006.11

  A series of 3,3′-disubstituted BINAP ligands are used in asymmetric inter- and intramolecular Heck/Mizoroki reactions and their enantioselectivity compared to BINAP.

  将一系列 3,3′-二取代的 BINAP 配体用于不对称分子间和分子内 Heck/Mizoroki 反应，并比较了它们与 BINAP 的对映选择性。
• Application of 3,3′-disubstituted xylBINAP derivatives in inter- and intramolecular asymmetric Heck/Mizoroki reactions
  作者：Danica A. Rankic、Daniela Lucciola、Brian A. Keay

  DOI：10.1016/j.tetlet.2010.08.078

  日期：2010.10

  3,3'-Disubstituted xylBINAP derivatives were applied to inter- and intramolecular asymmetric Heck/Mizoroki reactions. The results from these reactions were compared to those obtained with (R)-xylBINAP, (S)-BINAP and 3,3'-disubstituted BINAP derivatives. Catalysts derived from 3,3'-disubstituted xylBINAP ligands were found to be most effective in the arylation of 2,3-dihydrofuran in terms of reaction times, conversions, and product enantioselectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Catalytic asymmetric synthesis of quarternary carbon centers. Palladium-catalyzed formation of either enantiomer of spirooxindoles and related spirocyclics using a single enantiomer of a chiral diphosphine ligand
  作者：Atsuyuki Ashimori、Larry E. Overman

  DOI：10.1021/jo00043a005

  日期：1992.8

  The asymmetric synthesis of eight spirooxindoles and related spirocyclics from the corresponding aryl iodide by palladium catalyzed cyclizations in the presence of the diphosphine ligand (R)-(+)-BINAP is reported.