ethyl 5-chloro-3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate | 87423-64-1

• 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: ethyl 5-chloro-3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate
• 英文别名: Ethyl 5-chloro-3-hydroxy-1-methyl-2-oxoindole-3-carboxylate
• CAS: 87423-64-1
• 化学式: C₁₂H₁₂ClNO₄
• 分子量: 269.685
• InChiKey: NUWDZIKKTAETNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-((4-chlorophenyl)(methyl)amino)-3-oxopropanoate 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以90%的产率得到ethyl 5-chloro-3-hydroxy-1-methyl-2-oxoindoline-3-carboxylate
  参考文献：
  名称：

  Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides

  摘要：

  The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.

  DOI：

  10.1021/ol300418h

文献信息

• Oxazolidinedione derivatives
  申请人：PFIZER INC.

  公开号：EP0079675A1

  公开（公告）日：1983-05-25

  A series of novel spiro-oxindole oxazolidinedione derivatives have been prepared, including their base salts with pharmacologically acceptable cations. These compounds are useful in therapy as aldose reductase inhibitors for the control of certain chronic diabetic complications. Preferred compounds include 1-(p-fluorophenyl)-5-fluoro-spiro-[indoline-3,5'-oxazolidine]-2,2',4'-trione, 1-methyl-5-chloro- spiro-[indoline-3,5'-oxazolidine]-2,2',4'-trione, 1-isopropyl-5-chloro-spiro-[indoline-3,5'-oxazolidine]-2,2',4'-trione and 1-(p-chlorobenzyl)-5-chloro-spiro-[indoline-3,5'-oxazolidine]-2,2'-4'-trione. Methods for preparing these compounds from known starting materials are provided.

  我们制备了一系列新型螺吲哚噁唑烷二酮衍生物，包括它们与药理学上可接受的阳离子的基盐。这些化合物可作为醛糖还原酶抑制剂用于治疗，以控制某些慢性糖尿病并发症。首选化合物包括 1-(对氟苯基)-5-氟-螺-[吲哚啉-3,5'-恶唑烷]-2,2',4'-三酮、1-甲基-5-氯-螺-[吲哚啉-3,5'-恶唑烷]-2,2'、4'-三酮、1-异丙基-5-氯螺-[吲哚啉-3,5'-恶唑烷]-2,2',4'-三酮和 1-(对氯苄基)-5-氯螺-[吲哚啉-3,5'-恶唑烷]-2,2'-4'-三酮。提供了从已知起始材料制备这些化合物的方法。
• Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative C–C Bond Formation: Synthesis of 3-Hydroxy-2-oxindoles and Spirooxindoles from Anilides
  作者：Junwei Wang、Yucheng Yuan、Rui Xiong、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/ol300418h

  日期：2012.5.4

  The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO2Et) In CF3CH2OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R-4)Ar) afforded the C-2-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.