ethyl (R)-2-(4-methylphenylamino)propanoate | 940880-35-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (R)-2-(4-methylphenylamino)propanoate
• 英文别名: ethyl (2R)-2-(4-methylanilino)propanoate
• CAS: 940880-35-3
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: HCJFOQZMXYHOSU-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  水合氯醛 、 ethyl (R)-2-(4-methylphenylamino)propanoate 在 盐酸 、 盐酸羟胺 、 sodium sulfate 作用下， 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of isatins with a chiral substituent at the nitrogen atom

  摘要：

  (R)-Ethyl 2-(isatin-1-yl)propanoates 8a-c were prepared from the corresponding (R)-arylalanines by Sandmeyer's method in high yield and good enantioselectivity (up to 99%). The key step of the process is the Mitsunobu reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.015
• 作为产物：
  描述：

  ethyl (R)-N-(2-nitrophenylsulfonyl)-N-(4-methylphenyl)-2-aminopropanoate 在 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到ethyl (R)-2-(4-methylphenylamino)propanoate
  参考文献：
  名称：

  Synthesis of isatins with a chiral substituent at the nitrogen atom

  摘要：

  (R)-Ethyl 2-(isatin-1-yl)propanoates 8a-c were prepared from the corresponding (R)-arylalanines by Sandmeyer's method in high yield and good enantioselectivity (up to 99%). The key step of the process is the Mitsunobu reaction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.015

文献信息

• Asymmetric NH Insertion of Secondary and Primary Anilines under the Catalysis of Palladium and Chiral Guanidine Derivatives
  作者：Yin Zhu、Xiaohua Liu、Shunxi Dong、Yuhang Zhou、Wei Li、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201308501

  日期：2014.2.3

  Efficient enantioselective NH insertion reactions of secondary and primary anilines were catalyzed by palladium(0) in combination with chiral guanidine derivatives. A broad range of substituted anilines were tolerated, and the corresponding products were obtained in high yield (up to 99 %) with good enantioselectivity (up to 94 % ee) under mild reaction conditions. The NH insertion mechanism was

  钯（0）结合手性胍衍生物可催化仲苯胺和伯苯胺的高效对映选择性N NH插入反应。在宽泛的取代苯胺耐受性，并且在温和的反应条件下，以高收率（高达99％ee）和良好的对映选择性（高达94％ee）获得了相应的产物 。所述N个用的动力学同位素效应，对照实验中，HRMS，和光谱分析的研究考察ħ插入机构。
• Enantioselective insertion of carbenoids into N–H bonds catalyzed by chiral bicyclobisoxazoline copper(I) complexes
  作者：Paul Le Maux、Gérard Simonneaux

  DOI：10.1016/j.tet.2015.10.009

  日期：2015.12

  Chiral copper(I)-bicyclobisoxazoline complexes were found to catalyze the insertion of α-diazocarbonyl compounds into N–H bonds of aniline derivatives. The insertion reactions proceeded with high yields (78–99%) and enantioselectivities of up to 81% for the different α-diazopropionates. A predominant effect of the nature and the position of the substituents on the enantiocontrol of the reaction was

  发现手性铜（I）-双环双恶唑啉配合物可催化将α-重氮羰基化合物插入苯胺衍生物的NH键中。该插入反应的进行以高产率（78-99％）和高达81％，为不同的α-diazopropionates的对映选择性。观察到取代基的性质和位置对反应对映体控制的主要作用。
• Synthesis of isatins with a chiral substituent at the nitrogen atom
  作者：Alexander V. Kurkin、Anna A. Bernovskaya、Marina A. Yurovskaya

  DOI：10.1016/j.tetasy.2009.05.015

  日期：2009.7

  (R)-Ethyl 2-(isatin-1-yl)propanoates 8a-c were prepared from the corresponding (R)-arylalanines by Sandmeyer's method in high yield and good enantioselectivity (up to 99%). The key step of the process is the Mitsunobu reaction. (C) 2009 Elsevier Ltd. All rights reserved.