(R)-ethyl 2-(2,3-dioxoindolin-1-yl)propanoate | 1187671-00-6

• 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: (R)-ethyl 2-(2,3-dioxoindolin-1-yl)propanoate
• 英文别名: BB 0263354；(R)-ethyl 2-(isatin-1-yl)propanoate；ethyl (R)-2-(isatin-1-yl)propionate；(r)-Ethyl 2-(isatin-1-yl)propionate；ethyl (2R)-2-(2,3-dioxoindol-1-yl)propanoate
• CAS: 1187671-00-6
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: LRUPULYZEKQQTL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-ethyl 2-(2,3-dioxoindolin-1-yl)propanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(R)-ethyl 2-(2,4-dioxo-2H-3,1-benzoxazin-1(4H)-yl)propanoate
  参考文献：
  名称：

  Synthesis of N-alkylanthranilamides with a chiral substituent at the nitrogen atom

  摘要：

  Novel anthranilamides containing a chiral substituent at the nitrogen atom and different substituents on the benzene ring were prepared from the corresponding isatins in good yields and high enantioselectivities (up to 98%). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.001
• 作为产物：
  描述：

  在 硫酸 作用下， 生成 (R)-ethyl 2-(2,3-dioxoindolin-1-yl)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

• Comparative study of the different approaches to the synthesis of isatins with a chiral substituent at the nitrogen atom
  作者：A. V. Kurkin、A. A. Bernovskaya、M. A. Yurovskaya

  DOI：10.1007/s10593-011-0654-y

  日期：2011.1

  Through a comparative study of three different routes to the synthesis of isatins with a chiral substituent on the nitrogen atom it has been shown that better results for preparing the isatins are achieved using the Sandmeyer (>99% ee, yield 50%) rather than the Stolle method (95% ee, yield 16%). The procedure proposed by Gassman for preparing isatins was unsuitable for the compounds described.

  通过对三种在氮原子上具有手性取代基的靛红合成路线的比较研究，结果表明，使用Sandmeyer（> 99％ee，收率50％）而不是使用Sandmeyer可以更好地制备靛红。Stolle法（95％ee，收率16％）。Gassman提出的制备靛红的方法不适用于所描述的化合物。