2,2'-dimethyl-[2,2'-biindoline]-3,3'-dione | 23740-96-7

• 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: 2,2'-dimethyl-[2,2'-biindoline]-3,3'-dione
• 英文别名: 2,2'-dimethyl-2,2'-diindoxyl；2,2'-dimethyl-1,2,1',2'-tetrahydro-[2,2']biindolyl-3,3'-dione；2,2'-Dimethyl-1,2,1',2'-tetrahydro-[2,2']biindolyl-3,3'-dion；2,2'-Dimethyl-3,3'-dioxodiindolinyl-2,2'；2.2'-Dimethyl-diindoxylyl-(2.2')；2.2'-Dimethyl-diindoxyl-(2.2')；2-methyl-2-(2-methyl-3-oxo-1H-indol-2-yl)-1H-indol-3-one
• CAS: 23740-96-7
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: YPUBFBZMQZCELY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenylalanine-o-carboxylic acid 在 air 、 alkaline solution 、 sodium acetate 作用下， 生成 2,2'-dimethyl-[2,2'-biindoline]-3,3'-dione
  参考文献：
  名称：

  van Alphen, Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 895

  摘要：

  DOI：

文献信息

• Metal-free synthesis of 2,2-disubstituted indolin-3-ones
  作者：Xinpeng Jiang、Bingbin Zhu、Kai Lin、Guan Wang、Wei-Ke Su、Chuanming Yu

  DOI：10.1039/c8ob03057j

  日期：——

  straightforward method for the synthesis of indolin-3-ones bearing a C2-quaternary functionality is reported. A series of 2,2-disubstituted indolin-3-ones were constructed in up to 94% yields in the absence of a metal catalyst. This cross-coupling reaction allows the facile synthesis of 2,2-disubstituted indolin-3-ones from readily available substrates in a short reaction time.

  据报道，具有C 2-四元官能度的吲哚-3-酮的直接合成方法。在不存在金属催化剂的情况下，以高达94％的产率构建了一系列2,2-二取代的吲哚-3-酮。该交叉偶联反应允许在短的反应时间内从容易获得的底物容易地合成2，2-二取代的吲哚-3-酮。
• Synthesis of Bis (2-methyl-2-indolin-3-one)
  作者：Tomoyoshi KOMAI

  DOI：10.1248/cpb1953.4.314

  日期：——

  Bis (2-methyl-2-indolin-3-one) was synthesized from anthranilic acid and β-bromopropionic acid according to Alphen's method and also from indigo by reductive methylation. It was proved that this compound was identical with one of the products obtained from the reduction of ethyl indoxylate with lithium aluminum hydride.

  双（2-甲基-2-吲哚啉-3-酮）是根据 Alphen 的方法从蚁酸和 β-溴丙酸合成的，也是通过还原甲基化从靛蓝中合成的。实验证明，该化合物与用氢化铝锂还原吲哚乙酸乙酯得到的产物之一相同。
• New transformations of o-substituted azoxybenzenes
  作者：S. S. Mochalov、A. N. Fedotov、E. A. Kupriyanova、Yu. S. Shabarov

  DOI：10.1007/bf00514470

  日期：1983.5
• Komai, Pharmaceutical Bulletin, 1956, vol. 4, p. 261,265
  作者：Komai

  DOI：——

  日期：——
• Silver‐Mediated Cascade Synthesis of Functionalized 1,4‐Dihydro‐2 <i>H</i> ‐benzo‐1,3‐oxazin‐2‐ones from Carbon Dioxide
  作者：Xuetong Li、Jordi Benet‐Buchholz、Eduardo C. Escudero‐Adán、Arjan W. Kleij

  DOI：10.1002/anie.202217803

  日期：2023.3.6

  AbstractA conceptually novel catalytic domino approach is presented for the synthesis of highly functional 1,4‐dihydro‐2H‐1,3‐benzoxazine‐2‐one derivatives. Key to the chemoselectivity is a proper design of the precursor to override thermodynamically favored parasitic cyclization processes and empower the formation of the desired product through Thorpe–Ingold effects. The synthetic diversity of these CO2‐based heterocycles is further demonstrated, and the isolation of a reaction intermediate supports an unusual ring‐expansion sequence from an α‐alkylidene, five‐membered cyclic carbonate to a six‐membered cyclic carbamate by N‐induced isomerization.