1-butyl-3-hydroxy-3-phenylindolin-2-one | 136369-01-2

• 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: 1-butyl-3-hydroxy-3-phenylindolin-2-one
• 英文别名: 1-butyl-3-hydroxy-3-phenylisatin；1-Butyl-3-hydroxy-3-phenylindol-2-one
• CAS: 136369-01-2
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: SAHSZKGOTGNIMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-丁基-1H-吲哚-2,3-二酮 、 苯硼酸 在 dirhodium tetraacetate 、 C₁₂H₂₈P*BF₄ 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.33h， 以97%的产率得到1-butyl-3-hydroxy-3-phenylindolin-2-one
  参考文献：
  名称：

  Axial Tri-tert-butylphosphane Coordination to Rh₂(OAc)₄: Synthesis, Structure, and Catalytic Studies

  摘要：

  The introduction of strong sigma-donor axial ligands to the Rh-Rh metal bond has been utilized as an effective way to provide new chemical reactivities to bimetallic dirhodium(II) complexes. In this report, Rh-2(OAc)(4) complexes with axial bulky alkylphosphane ligands (PR3), in particular P(t- Bu)(3), were prepared and characterized. The net sigma-donation from the PR3 to the Rh-Rh bond is the result of the competition between the electron-donating ability of the R group and the steric profile of the PR3 at the Rh-2 core. Analysis of the crystal structure data showed that the strong sigma-donor P(t-Bu)(3) coordinates to the rhodium with an amount of sigma-donation to the rhodium similar to that of the aryl phosphane ligand PPh3, but has an unusually long Rh-P bond distance (2.663 angstrom). During catalytic trials to synthesize 3-aryl-3-hydroxy-2-oxindole by the addition of arylboronic acids to isatin derivatives, this longer Rh-P bond distance in Rh-2(OAc)(4)(P(t-Bu)(3))(2) (Cat-1) facilitates substitution of one of the axial phosphane ligands by the arylboronic acid. This sigma-donating effect greatly accelerated the arylation reaction in comparison to alternative catalysts. Additionally, Rh-2(OAc)(4) was easily recovered after completion of the reaction.

  DOI：

  10.1021/acs.organomet.6b00477

文献信息

• Copper-catalyzed arylation of indolin-2,3-ones with arylboronic acids
  作者：Jilei Zhang、Jiuxi Chen、Jinchang Ding、Miaochang Liu、Huayue Wu

  DOI：10.1016/j.tet.2011.09.135

  日期：2011.12

  A convenient and efficient Cu(OTf)(2)-catalyzed arylation of indolin-2,3-ones with arylboronic acids using cheap 1,10-phenanthroline hydrate as ligand was developed under air atmosphere, achieving 3-aryl-3-hydroxy-2-oxindoles in good to excellent yields. This catalytic system shows broad functional group tolerance. Moreover, the rigorous exclusion of air/moisture is not required in these transformations. (C) 2011 Elsevier Ltd. All rights reserved.
• Nishio, Takehiko, Journal of the Chemical Society. Perkin transactions I, 1991, # 7, p. 1717 - 1720
  作者：Nishio, Takehiko

  DOI：——

  日期：——
• Axial Tri-<i>tert</i>-butylphosphane Coordination to Rh₂(OAc)₄: Synthesis, Structure, and Catalytic Studies
  作者：Jiantao Tan、Yi Kuang、Yi Wang、Qingfei Huang、Jin Zhu、Yuanhua Wang

  DOI：10.1021/acs.organomet.6b00477

  日期：2016.9.26

  The introduction of strong sigma-donor axial ligands to the Rh-Rh metal bond has been utilized as an effective way to provide new chemical reactivities to bimetallic dirhodium(II) complexes. In this report, Rh-2(OAc)(4) complexes with axial bulky alkylphosphane ligands (PR3), in particular P(t- Bu)(3), were prepared and characterized. The net sigma-donation from the PR3 to the Rh-Rh bond is the result of the competition between the electron-donating ability of the R group and the steric profile of the PR3 at the Rh-2 core. Analysis of the crystal structure data showed that the strong sigma-donor P(t-Bu)(3) coordinates to the rhodium with an amount of sigma-donation to the rhodium similar to that of the aryl phosphane ligand PPh3, but has an unusually long Rh-P bond distance (2.663 angstrom). During catalytic trials to synthesize 3-aryl-3-hydroxy-2-oxindole by the addition of arylboronic acids to isatin derivatives, this longer Rh-P bond distance in Rh-2(OAc)(4)(P(t-Bu)(3))(2) (Cat-1) facilitates substitution of one of the axial phosphane ligands by the arylboronic acid. This sigma-donating effect greatly accelerated the arylation reaction in comparison to alternative catalysts. Additionally, Rh-2(OAc)(4) was easily recovered after completion of the reaction.