(E)-1-acetyl-3-benzylidene-5-methoxyindolin-2-one | 1259283-62-9

• 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: (E)-1-acetyl-3-benzylidene-5-methoxyindolin-2-one
• CAS: 1259283-62-9
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: VTXSLVWYSDLVDI-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-1-acetyl-3-benzylidene-5-methoxyindolin-2-one 、 ethyl 4-phenylbuta-2,3-dienoate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以95%的产率得到ethyl 1'-acetyl-5'-methoxy-2'-oxo-2,5-diphenylspiro[cyclopent[3]ene-1,3'-indoline]-3-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

  摘要：

  The phosphine-promoted [3 + 2] cyclizations between gamma-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh3 operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

  DOI：

  10.1021/jo302460d

文献信息

• An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles
  作者：Arnaud Voituriez、Nathalie Pinto、Mathilde Neel、Pascal Retailleau、Angela Marinetti

  DOI：10.1002/chem.201001791

  日期：2010.11.8

  Power of P: Phosphine‐promoted [3+2] annulation reactions between electron‐poor allenes and 3‐arylidene indolin‐2‐ones afford a new organocatalytic strategy for the synthesis of the spirocyclic core of oxindolic cyclopentanes (see scheme). Asymmetric variants of these reactions have been implemented by using chiral catalysts, giving very high levels of asymmetric induction.

  P的力量：电子贫乏的烯与3-芳基吲哚-2-酮之间的膦促进的[3 + 2]环化反应为合成羟吲哚环戊烷的螺环核提供了一种新的有机催化策略（参见方案）。通过使用手性催化剂已经实现了这些反应的不对称变体，产生了非常高水平的不对称诱导。