6-bromo-3-(4-methoxyphenyl)imino-1H-indol-2-one | 1354636-93-3

• 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: 6-bromo-3-(4-methoxyphenyl)imino-1H-indol-2-one
• CAS: 1354636-93-3；1369382-16-0；1369382-38-6
• 化学式: C₁₅H₁₁BrN₂O₂
• 分子量: 331.169
• InChiKey: SNQDQSXORZBPJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-isothiocyanatooxindole 、 6-bromo-3-(4-methoxyphenyl)imino-1H-indol-2-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.73h， 生成 、
  参考文献：
  名称：

  Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro[imidazolidine-2-thione]bisoxindoles

  摘要：

  An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.

  DOI：

  10.1021/ol203081x

文献信息

• Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles
  作者：Qi-Xiang Guo、Yu-Wan Liu、Xing-Cheng Li、Ling-Zhi Zhong、Yun-Gui Peng

  DOI：10.1021/jo202585w

  日期：2012.4.6

  The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone is reported. The chiral primary amino acid catalyzed this Mannich reaction to afford both anti- and syn-Mannich adducts in high yields, good diastereoselectivities, and enantioselectivities. The reason for the solvent control of the diastereoselectivity phenomenon was investigated.

  报道了靛红亚胺与羟丙酮的非对映选择性可切换的对映选择性曼尼希反应。手性伯氨基酸催化此曼尼希反应，得到既抗和顺式以高产率，良好的非对映选择性，和对映选择性-Mannich加合物。研究了溶剂控制非对映选择性现象的原因。
• Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro[imidazolidine-2-thione]bisoxindoles
  作者：Yan-Yan Han、Wen-Bing Chen、Wen-Yong Han、Zhi-Jun Wu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/ol203081x

  日期：2012.1.20

  An efficient and stereoselective reaction between 3-isothiocyanato oxindoles and isatins/isatinimines has been developed to afford structurally diverse dispiro[oxazolidine-2-thione]bisoxindoles and dispiro[imidazolidine-2-thione]bisoxindoles in excellent results under mild conditions. The potential of asymmetric induction by means of a chiral auxiliary was explored. The isomers are separable, and products could be isolated as single diastereomers by column chromatography. Further synthetic transformations of the reaction product were also successfully realized.