(3S)-1,3-dimethyl-3-{β-[(methoxycarbonyl)amino]ethyl}-5-methoxyoxindole | 131042-90-5

• 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: (3S)-1,3-dimethyl-3-{β-[(methoxycarbonyl)amino]ethyl}-5-methoxyoxindole
• 英文别名: methyl N-[2-[(3S)-5-methoxy-1,3-dimethyl-2-oxoindol-3-yl]ethyl]carbamate
• CAS: 131042-90-5
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: AIUFGUOBKPUXHA-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-1,3-dimethyl-3-{β-[(methoxycarbonyl)amino]ethyl}-5-methoxyoxindole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (3AS,8AR)-5-甲氧基-1,3A,8-三甲基-1,2,3,3A,8,8A-六氢吡咯并[2,3-B]吲哚
  参考文献：
  名称：

  Synthesis of (−)- and (+)-esermethole via chemical resolution of 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole

  摘要：

  A new synthesis of (-)- and (+)-esermethole (2 and 7 respectively), penultimate intermediates to (-)- and (+)-physostigmine, is described. Phase-transfer catalyzed dimethylation of 3-cyanomethyl -5-methoxyoxindole (3) and successive hydrogenation of the cyano group gave 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole (5), which was efficiently resolved with optically active tartaric acids. Subsequent conversion to a carbamate and reductive cyclization performed by a standard method afforded both the enantiomers of esermethole. The enantiomeric excesses, determined by chiral HPLC analysis, were greater than 99.5%. In particular, analytical HPLC resolution of 5, previously reported as unfeasible, was achieved.

  DOI：

  10.1016/s0957-4166(00)80490-5
• 作为产物：
  描述：

  1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3S)-1,3-dimethyl-3-{β-[(methoxycarbonyl)amino]ethyl}-5-methoxyoxindole
  参考文献：
  名称：

  Synthesis of (−)- and (+)-esermethole via chemical resolution of 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole

  摘要：

  A new synthesis of (-)- and (+)-esermethole (2 and 7 respectively), penultimate intermediates to (-)- and (+)-physostigmine, is described. Phase-transfer catalyzed dimethylation of 3-cyanomethyl -5-methoxyoxindole (3) and successive hydrogenation of the cyano group gave 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole (5), which was efficiently resolved with optically active tartaric acids. Subsequent conversion to a carbamate and reductive cyclization performed by a standard method afforded both the enantiomers of esermethole. The enantiomeric excesses, determined by chiral HPLC analysis, were greater than 99.5%. In particular, analytical HPLC resolution of 5, previously reported as unfeasible, was achieved.

  DOI：

  10.1016/s0957-4166(00)80490-5

文献信息

• Enantioselective Creation of Quaternary Carbon Centers through Addition- Elimination Reaction: Asymmetric Nitroolefination of 3-Substituted 2-Oxindoles
  作者：Kaoru Fuji、Takeo Kawabata、Toshiumi Ohmori、Muhong Shang、Manabu Node

  DOI：10.3987/com-97-s(n)107

  日期：——

  Nitroolefination of 3-substituted 2-oxindoles with nitroenamine (5) afforded the corresponding products having quaternary carbon centers with high ee in good yield. Application of this method to concise syntheses of (-)-esermethole (24) and (-)-pseudophrynaminol (28) is described.
• Asymmetric alkylation of oxindoles: an approach to the total synthesis of (-)-physostigmine
  作者：Thomas B. K. Lee、George S. K. Wong

  DOI：10.1021/jo00002a074

  日期：1991.1
• LEE, THOMAS B. K.;WONG, GEORGE S. K., J. ORG. CHEM., 56,(1991) N, C. 872-875
  作者：LEE, THOMAS B. K.、WONG, GEORGE S. K.

  DOI：——

  日期：——