(S)-5-chloro-2-hydroxy-1-oxo-N-phenyl-2,3-dihydro-1H-indene-2-carboxamide | 1422194-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (S)-5-chloro-2-hydroxy-1-oxo-N-phenyl-2,3-dihydro-1H-indene-2-carboxamide
• 英文别名: (2S)-6-chloro-2-hydroxy-3-oxo-N-phenyl-1H-indene-2-carboxamide
• CAS: 1422194-01-1
• 化学式: C₁₆H₁₂ClNO₃
• 分子量: 301.729
• InChiKey: ZSMYPMDZOGHPJH-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-chloro-1-oxo-N-phenyl-2,3-dihydro-1H-indene-2-carboxamide 在 C₃₃H₃₀Br₂F₃N₂O⁽¹⁺⁾*Br^(1-) 、 caesium carbonate 作用下， 以 水 、 间二甲苯 为溶剂， 反应 24.0h， 以29%的产率得到
  参考文献：
  名称：

  Cinchona衍生的相转移催化剂分批和半流式催化可见光驱动的β-二羰基化合物的对映选择性好氧氧化

  摘要：

  β-二羰基化合物的直接不对称α-羟基化反应是使用金鸡纳衍生的相转移手性光催化剂在间歇和半流过程中开发的。使用可见光作为驱动力，并使用空气作为氧化剂，可以以优异的收率（高达96％）和良好的对映选择性（高达90％ee）获得相应的产物。催化剂充当手性中心和催化中心，并与底物形成手性烯醇盐配合物，以在反应中充当光敏中心。使用半流式光化学工艺可以缩短反应时间（24 h至0.89 h），并获得良好的收率（高达93％）和对映选择性（高达ee的88％）。

  DOI：

  10.1002/adsc.201900777

文献信息

• Enantioselective α-hydroxylation of β-ketoamides
  作者：Claudia De Fusco、Sara Meninno、Consiglia Tedesco、Alessandra Lattanzi

  DOI：10.1039/c2ob27283k

  日期：——

  The first enantioselective α-hydroxylation reaction of α-substituted β-ketoamides has been developed by using the commercially available hydroquinine/TBHP system. The tertiary alcohols are obtained in good to high yield and up to 83% ee, which can be improved by a single crystallization.

  通过使用可商购的产品开发了第一个α-取代的β-酮酰胺的对映选择性α-羟基化反应 对苯二酚/ TBHP系统。可以以高至高收率和高达83％ee的价格获得叔醇，这可以通过单次结晶来改进。
• Asymmetric α-hydroxylation of β-dicarbonyl compounds by C-2′ modified cinchonine-derived phase-transfer catalysts in batch and flow microreactors
  作者：Xiao-Fei Tang、Jing-Nan Zhao、Yu-Feng Wu、Ze-Hao Zheng、Cun-Fei Ma、Zong-Yi Yu、Lei Yun、Guang-Zhi Liu、Qing-Wei Meng

  DOI：10.1080/00397911.2020.1781183

  日期：2020.8.17

  Abstract The asymmetric α-hydroxylation of β-dicarbonyl compounds was catalyzed by C-2′-modified cinchonine-derived phase-transfer catalysts. Excellent yields (up to 95%) and good enantioselectivities (up to 89% ee) were obtained. The reaction was carried out in a flow microreactor and similar results were obtained (up to 93% yield, 84% ee), the residence time was shortened from 24 h in batch to 2 h

  摘要 β-二羰基化合物的不对称α-羟基化是由C-2'-修饰的辛可宁衍生的相转移催化剂催化的。获得了优异的产率（高达 95%）和良好的对映选择性（高达 89% ee）。该反应在流动微反应器中进行，获得了相似的结果（产率高达 93%，ee 为 84%），停留时间从分批的 24 小时缩短到 2 小时。图形概要
• Development of C-6′-modified quinine-derived phase-transfer catalysts and their application in the enantioselective α-hydroxylation of β-dicarbonyl compounds
  作者：Hai Qing、Yakun Wang、Zehao Zheng、Shuai Chen、Qingwei Meng

  DOI：10.1016/j.tetasy.2016.07.006

  日期：2016.10

  We have developed C-6'-modified quinine quaternary ammonium salts as phase transfer catalysts for alpha-hydroxylation of beta-dicarbonyl compounds. The quinine quaternary ammonium salts, which was modified at C-6' and the N atom, had good activity for alpha-hydroxylation of B-dicarbonyl compounds. By using 5 mol % of 6-hydroxyl-N-(4'-fluoro-2'-trifluoromethyl)quinine quaternary ammonium salt as the organocatalyst, cumene hydroperoxide as the oxidant, toluene as the solvent, and 50% K2HPO4 as the aqueous alkali at room, temperature, the yield and enantioselectivity of the alpha-hydroxylation of beta-keto esters were 95% and 88%, respectively. This catalytic system was also applicable for beta-keto amides (92% yield and 76% ee). (C) 2016 Elsevier Ltd. All rights reserved.