(-)-5-methoxyindolmycin | 1070325-98-2

• 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: (-)-5-methoxyindolmycin
• 英文别名: (5S)-5-[(1R)-1-(5-methoxy-1H-indol-3-yl)ethyl]-2-methylimino-1,3-oxazolidin-4-one
• CAS: 1070325-98-2
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: QCPSKIBGYKVEHT-OQPBUACISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S)-2-amino-5-[(1R)-1-(5-methoxy-1H-indol-3-yl)ethyl]-1,3-oxazol-4-one 、 甲胺 以 水 为溶剂， 反应 12.0h， 以198 mg的产率得到(-)-5-methoxyindolmycin
  参考文献：
  名称：

  A concise synthesis of (−)-indolmycin and (−)-5-methoxyindolmycin

  摘要：

  Concise syntheses of (-)-indolmycin 1 and (-)-5-methoxyindolmycin 3 were developed based on a palladium-catalyzed reaction of (2S,3R)-2-acetoxy-3-methyl-5-trimethylsilyl-4-pentynoate 6 with an o-iodoaniline derivative 10 or 11, followed by reaction with guanidine hydrochloride in the presence of base. An optically active internal alkyne (2S 3R)-6 was obtained by lipase-assisted enantioselective acetylation of (+/-)-(2,3)-syn-2-hydroxy-3-methyl-5-trimethylsily-4-pentynoate 4. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.013

文献信息

• A concise synthesis of (−)-indolmycin and (−)-5-methoxyindolmycin
  作者：Noriyuki Sutou、Keisuke Kato、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2008.07.013

  日期：2008.8

  Concise syntheses of (-)-indolmycin 1 and (-)-5-methoxyindolmycin 3 were developed based on a palladium-catalyzed reaction of (2S,3R)-2-acetoxy-3-methyl-5-trimethylsilyl-4-pentynoate 6 with an o-iodoaniline derivative 10 or 11, followed by reaction with guanidine hydrochloride in the presence of base. An optically active internal alkyne (2S 3R)-6 was obtained by lipase-assisted enantioselective acetylation of (+/-)-(2,3)-syn-2-hydroxy-3-methyl-5-trimethylsily-4-pentynoate 4. (C) 2008 Elsevier Ltd. All rights reserved.