1-benzyl-3-hydroxy-7-methyl-3-phenylindolin-2-one | 1222534-61-3

• 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-benzyl-3-hydroxy-7-methyl-3-phenylindolin-2-one
• 英文别名: 1-Benzyl-3-hydroxy-7-methyl-3-phenylindol-2-one；1-benzyl-3-hydroxy-7-methyl-3-phenylindol-2-one
• CAS: 1222534-61-3
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: SRMBRTFSFVQZJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-hydroxy-7-methyl-3-phenylindolin-2-one 在 叠氮基三甲基硅烷 、 三氟乙酸 作用下， 以91 %的产率得到1-benzyl-8-methyl-3-phenylquinoxalin-2(1H)-one
  参考文献：
  名称：

  Expanding the Potential of 3‐Hydroxyindolinones: Synthesis of Quinoxalin‐2(1H)‐ones through Acid‐Promoted Azidation and Ring‐Expansion

  摘要：

  摘要 我们在此报告了一种从 3-羟基吲哚啉-2-酮衍生物合成喹喔啉-2(1H)-酮的方法。该反应是通过一个碳位化合物在 CF3CO2H 介导下发生叠氮反应，然后在酸的诱导下发生 N2 挤压和扩环反应。研究发现，CF3CO2H 和溶剂 1,1,1,3,3,3-六氟-2-丙醇对这一重排反应至关重要。产物中完全保留了 3-hydroxyindolin-2-one 骨架的轴向手性。

  DOI：

  10.1002/adsc.202300685
• 作为产物：
  描述：

  2-(dibenzylamino)-N,N-diethyl-3-methylbenzamide 在 正丁基锂 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 1.0h， 以53%的产率得到1-benzyl-3-hydroxy-7-methyl-3-phenylindolin-2-one
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement

  摘要：

  Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.159

文献信息

• 10.1016/j.tetlet.2024.155117
  作者：Liu, Jian、Wang, Bingfu、Li, Tianxing、Jin, Hui、Zhang, Lixin

  DOI：10.1016/j.tetlet.2024.155117

  日期：——

  proline was designed and synthesized as a bifunctional organocatalyst for the “on-water” asymmetric Michael addition of less-hydrophobic oxoindoles to nitroolefins. Employing only 1 mol% of this bifunctional organocatalyst demonstrated exceptional catalytic efficiency (>90 % yield in most cases) and stereoselectivity in reactions involving various 3-substituted oxoindoles (up to > 99 % de and 96 % ee) and

  设计并合成了由脯氨酸衍生的二氯苯基取代的手性脲，作为双功能有机催化剂，用于疏水性较低的氧代吲哚与硝基烯烃的“水上”不对称迈克尔加成。仅使用 1 mol% 的这种双功能有机催化剂，在涉及各种 3-取代氧代吲哚（高达 > 99% de 和 96% ee）和硝基烯烃（高达 > 99% de 和 98% ee）。
• Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement
  作者：Iain Coldham、Harry Adams、Neil J. Ashweek、Thomas A. Barker、Andrew T. Reeder、Melanie C. Skilbeck

  DOI：10.1016/j.tetlet.2010.02.159

  日期：2010.5

  Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.
• Expanding the Potential of 3‐Hydroxyindolinones: Synthesis of Quinoxalin‐2(1<i>H</i>)‐ones through Acid‐Promoted Azidation and Ring‐Expansion
  作者：Shuming Zhan、Heng Xu、Wenjing Guo、Lin Li、Biqiong Hong、Zhenhua Gu

  DOI：10.1002/adsc.202300685

  日期：2023.10.24

  We report herein a synthesis of quinoxalin‐2(1H)‐ones from 3‐hydroxyindolin‐2‐one derivatives, which can be synthesized from commercially available isatins in one or two steps. The reaction proceeded through a CF₃CO₂H‐mediated azidation via a carbocation, followed by acid‐induced N₂ extrusion and ring‐expansion. Both CF₃CO₂H and the solvent 1,1,1,3,3,3‐hexafluoro‐2‐propanol were found to be crucial for this rearrangement. The axial chirality in 3‐hydroxyindolin‐2‐one skeleton was fully preserved in the products.

  摘要 我们在此报告了一种从 3-羟基吲哚啉-2-酮衍生物合成喹喔啉-2(1H)-酮的方法。该反应是通过一个碳位化合物在 CF3CO2H 介导下发生叠氮反应，然后在酸的诱导下发生 N2 挤压和扩环反应。研究发现，CF3CO2H 和溶剂 1,1,1,3,3,3-六氟-2-丙醇对这一重排反应至关重要。产物中完全保留了 3-hydroxyindolin-2-one 骨架的轴向手性。