(3R,4'S)-5-bromo-4'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2'-thioxospiro[indoline-3,5'-oxazolidin]-2-one | 1335018-73-9

• 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: (3R,4'S)-5-bromo-4'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2'-thioxospiro[indoline-3,5'-oxazolidin]-2-one
• 英文别名: (4S,5R)-5'-bromo-4-(4,4-dimethyl-2-oxo-1,3-oxazolidine-3-carbonyl)-2-sulfanylidenespiro[1,3-oxazolidine-5,3'-1H-indole]-2'-one
• CAS: 1335018-73-9
• 化学式: C₁₆H₁₄BrN₃O₅S
• 分子量: 440.274
• InChiKey: CNGBBWZTCGPGGT-QLJPJBMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(2-isothiocyanatoacetyl)-4,4-dimethyloxazolidin-2-one 、 5-溴靛红 在 普瑞巴林杂质D 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (3R,4'S)-5-bromo-4'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2'-thioxospiro[indoline-3,5'-oxazolidin]-2-one 、 (3R,4'S)-5-bromo-4'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2'-thioxospiro[indoline-3,5'-oxazolidin]-2-one 、 5-bromo-4'-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2'-thioxospiro[indoline-3,5'-oxazolidin]-2-one
  参考文献：
  名称：

  Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds

  摘要：

  The organocatalytic enantioselective tandem aldol-cyclization reactions of a-isothiocyanato imides and activated carbonyl compounds, such as isatins, an alpha-ketolactone and a 1,2-dione, have been studied with cinchona alkaloid-derived thiourea-catalysts. This methodology provided an easy way to access enantiomerically enriched spirobicyclic thiocarbamates with high yields and good to excellent stereoselectivity, which have been demonstrated to be useful precursors for the synthesis of biologically active molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.028

文献信息

• Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds
  作者：Jie Guang、Cong-Gui Zhao

  DOI：10.1016/j.tetasy.2011.06.028

  日期：2011.6

  The organocatalytic enantioselective tandem aldol-cyclization reactions of a-isothiocyanato imides and activated carbonyl compounds, such as isatins, an alpha-ketolactone and a 1,2-dione, have been studied with cinchona alkaloid-derived thiourea-catalysts. This methodology provided an easy way to access enantiomerically enriched spirobicyclic thiocarbamates with high yields and good to excellent stereoselectivity, which have been demonstrated to be useful precursors for the synthesis of biologically active molecules. (C) 2011 Elsevier Ltd. All rights reserved.