(3E)-1-acetyl-6-chloro-3-[(3-chlorophenyl)methylidene]indol-2-one | 1210071-78-5

• 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: (3E)-1-acetyl-6-chloro-3-[(3-chlorophenyl)methylidene]indol-2-one
• CAS: 1210071-78-5
• 化学式: C₁₇H₁₁Cl₂NO₂
• 分子量: 332.186
• InChiKey: PFVNLPAPOVVXEI-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-phenylpenta-2,3-dienoate 、 (3E)-1-acetyl-6-chloro-3-[(3-chlorophenyl)methylidene]indol-2-one 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以68%的产率得到
  参考文献：
  名称：

  Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4 + 2] Cyclizations

  摘要：

  Triphenylphosphine promoted reactions between 3-arylideneoxindoles and (delta-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted (delta-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.

  DOI：

  10.1021/ol401798w

文献信息

• Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition for the Synthesis of Spiro[4-cyclohexanone-1,3′-oxindoline] Derivatives in High Optical Purity
  作者：Qiang Wei、Liu-Zhu Gong

  DOI：10.1021/ol100020v

  日期：2010.3.5

  A bifunctional organocatalytic asymmetric formal [4 + 2] cycloaddition reaction of Nazarov reagents and methyleneindolinones afforded spiro[4-cyclohexanone-1,3′-oxindoline] derivatives with excellent enantioselectivity (up to 98% ee).

  Nazarov试剂和亚甲基吲哚满酮的双官能有机催化不对称形式[4 + 2]环加成反应，可得到具有出色对映选择性（最高98％ee）的螺[4-环己酮-1,3'-氧代吲哚啉]衍生物。
• Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications
  作者：Catherine Gomez、Maxime Gicquel、Jean-Christophe Carry、Laurent Schio、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1021/jo302460d

  日期：2013.2.15

  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.
• Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4 + 2] Cyclizations
  作者：Maxime Gicquel、Catherine Gomez、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1021/ol401798w

  日期：2013.8.2

  Triphenylphosphine promoted reactions between 3-arylideneoxindoles and (delta-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted (delta-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.