3-(3-nitrobenzyl)indolin-2-one | 1376933-08-2

• 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: 3-(3-nitrobenzyl)indolin-2-one
• CAS: 1376933-08-2
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: NRGLUDUMJOSDMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(3-nitrobenzyl)indolin-2-one 在 NO-Feng-PDiPPPi 、 scandium tris(trifluoromethanesulfonate) 、 sodium carbonate 、 N-氟代双苯磺酰胺 作用下， 以 氯仿 为溶剂， 反应 72.5h， 以98%的产率得到3-fluoro-3-(3-nitrobenzyl)indolin-2-one
  参考文献：
  名称：

  Highly Enantioselective Fluorination of Unprotected 3-Substituted Oxindoles: One-Step Synthesis of BMS 204352 (MaxiPost)

  摘要：

  The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.

  DOI：

  10.1021/jo301705t

文献信息

• Chiral Scandium(III)-Catalyzed Enantioselective α-Arylation of N-Unprotected 3-Substituted Oxindoles with Diaryliodonium Salts
  作者：Jing Guo、Shunxi Dong、Yulong Zhang、Yulong Kuang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201303602

  日期：2013.9.23

  Catalytic asymmetric α‐arylation of N‐unprotected 3‐substituted oxindoles with diaryliodonium salts has been realized by a chiral Lewis acid promoted electrophilic addition and aryl‐rearrangement process. Single C3‐arylated products containing a quaternary carbon center were generated in high enantioselectivity and reactivity.

  N手性路易斯酸促进亲电加成和芳基重排过程实现了N-未保护的3-取代的羟吲哚与二芳基碘鎓盐的催化不对称α-芳基化反应。具有高对映选择性和反应性的单个C3芳基化产物包含一个季碳中心。
• Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
  作者：Zhen Wang、Tengfei Kang、Qian Yao、Jie Ji、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.201500833

  日期：2015.5.18

  3‐substituted oxindoles to dienyl ketones has been developed. This procedure tolerates a relatively wide range of 3‐substituted oxindoles under mild conditions, facilitating the preparation of various chiral oxindoles with quaternary stereocenters. In addition, the reliable catalyst was found to be effective in the asymmetric 1,6‐addition of both δ‐unsubstituted and δ‐methyl‐substituted dienyl ketones, achieving

  已开发出第一个以N，N'-二氧化物– Sc III催化3 –取代的羟吲哚与二烯基酮进行1,6加成的例子。在温和的条件下，该方法可耐受相对广泛的3-取代的羟吲哚，从而有助于制备具有四级立体中心的各种手性羟吲哚。此外，还发现可靠的催化剂可有效地对δ未取代和δ甲基取代的二烯基酮进行不对称的1,6加成反应，从而实现出色的区域选择性和对映选择性（最高ee > 99％）。
• Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality
  作者：Jianlin Zhang、Yulong Zhang、Lili Lin、Qian Yao、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c5cc03203b

  日期：——

  The asymmetric Michael addition/desymmetrization reaction catalyzed by a N,N′-dioxide-Sc(iii) complex was realized, leading to the succinimides with two kinds of stereogenic elements—atom chirality and axial chirality in up to 99% yield, 99% ee and >19 : 1 d.r.

  由一个N,N'-二氧化物-Sc(iii)配合物催化的不对称Michael加成/去对称化反应已被实现，导致琥珀酰亚胺产率高达99％，对映异构体纯度为99％，且具有两种立体异构元素 - 原子手性和轴向手性，d.r.> 19:1。
• Catalytic Asymmetric Sulfenylation of Unprotected 3-Substituted Oxindoles
  作者：Yunfei Cai、Jun Li、Weiliang Chen、Mingsheng Xie、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1021/ol3009446

  日期：2012.6.1

  Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles has been developed via cooperative catalysis of a chiral N,N-dioxide-Sc(OTf)(3) complex and a Bronsted base. Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields with excellent enantioselectivities under mild reaction conditions.