(+)-5'-(2-methoxyphenyl)-1-methyl-2'-thioxospiro[indoline-3,4'-oxazolidin]-2-one

• 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: (+)-5'-(2-methoxyphenyl)-1-methyl-2'-thioxospiro[indoline-3,4'-oxazolidin]-2-one
• 英文别名: (4S,5S)-5-(2-methoxyphenyl)-1'-methyl-2-sulfanylidenespiro[1,3-oxazolidine-4,3'-indole]-2'-one
• 化学式: C₁₈H₁₆N₂O₃S
• 分子量: 340.403
• InChiKey: BOLWKRQDNYGHPN-YJBOKZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-isothiocyanato-1-methylindolin-2-one 、 邻甲氧基苯甲醛 在 N-[3,5-双（三氟甲基）苯基]-N''-[（1R，2R）-2-（二甲基氨基）-1,2-二苯基乙基]硫脲 作用下， 以 均三甲苯 为溶剂， 反应 0.02h， 以82%的产率得到(+)-5'-(2-methoxyphenyl)-1-methyl-2'-thioxospiro[indoline-3,4'-oxazolidin]-2-one
  参考文献：
  名称：

  Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction

  摘要：

  A highly efficient method for the construction of a family of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via a cascade aldol-cyclization process has been developed. This method provides access to spiro[oxazolidine-2-thione-oxindole] derivatives bearing two vicinal quaternary/tertiary stereocenters in up to 95% yield, 98:2 dr, and 89% ee with a chiral bifunctional thiourea tertiary amine organocatalyst based on DPEN scaffold. Good reactivity was observed and the reaction could be completed within 1.0 min. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.002

文献信息

• Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction
  作者：Wen-Bing Chen、Wen-Yong Han、Yan-Yan Han、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2013.05.002

  日期：2013.7

  A highly efficient method for the construction of a family of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via a cascade aldol-cyclization process has been developed. This method provides access to spiro[oxazolidine-2-thione-oxindole] derivatives bearing two vicinal quaternary/tertiary stereocenters in up to 95% yield, 98:2 dr, and 89% ee with a chiral bifunctional thiourea tertiary amine organocatalyst based on DPEN scaffold. Good reactivity was observed and the reaction could be completed within 1.0 min. (C) 2013 Elsevier Ltd. All rights reserved.