(S)-tert-butyl 3-chloro-7-fluoro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylate | 1273020-64-6

• 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: (S)-tert-butyl 3-chloro-7-fluoro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylate
• 英文别名: tert-butyl 3-chloro-7-fluoro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylate；tert-butyl (3S)-3-chloro-7-fluoro-3-(4-fluorophenyl)-2-oxoindole-1-carboxylate
• CAS: 1273020-64-6
• 化学式: C₁₉H₁₆ClF₂NO₃
• 分子量: 379.791
• InChiKey: BHLGUXHPDGLXOF-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 7-fluoro-3-(4-fluorophenyl)-2-oxo-3H-indole-1-carboxylate 在 N-氯代丁二酰亚胺 、 Ca[(S)-VAPOL-Phosphate]2 作用下， 以 醋酸异丙酯 为溶剂， 反应 0.5h， 以99%的产率得到(S)-tert-butyl 3-chloro-7-fluoro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  手性钙VAPOL磷酸盐介导的3-取代羟吲哚的不对称氯化和迈克尔反应

  摘要：

  我们公开了一种新型的高产率和高对映选择性手性钙 VAPOL 磷酸催化的 3-取代羟吲哚与 N-氯代琥珀酰亚胺 (NCS) 的氯化。该反应条件也显示出对 3-芳基羟吲哚与甲基乙烯基酮的催化对映选择性迈克尔加成有效。

  DOI：

  10.1021/ja109824x

文献信息

• Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles
  作者：Wenhua Zheng、Zuhui Zhang、Matthew J. Kaplan、Jon C. Antilla

  DOI：10.1021/ja109824x

  日期：2011.3.16

  We disclose a novel high yielding and highly enantioselective chiral calcium VAPOL phosphate-catalyzed chlorination of 3-substituted oxindoles with N-chlorosuccinimide (NCS). The reaction conditions are also shown to be effective for the catalytic enantioselective Michael addition of 3-aryloxindoles to methyl vinyl ketone.

  我们公开了一种新型的高产率和高对映选择性手性钙 VAPOL 磷酸催化的 3-取代羟吲哚与 N-氯代琥珀酰亚胺 (NCS) 的氯化。该反应条件也显示出对 3-芳基羟吲哚与甲基乙烯基酮的催化对映选择性迈克尔加成有效。
• Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles
  作者：Xing Gao、Jianwei Han、Limin Wang

  DOI：10.1021/acs.orglett.5b02323

  日期：2015.9.18

  A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.