(S)-methyl 2-(3-chloro-6-hydroxy-2-methylbenzamido)-3-(indol-3-yl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-methyl 2-(3-chloro-6-hydroxy-2-methylbenzamido)-3-(indol-3-yl)propanoate
• 化学式: C₂₀H₁₉ClN₂O₄
• 分子量: 386.835
• InChiKey: BADCAUYQCAFJDY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.42
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(3-chloro-6-hydroxy-2-methylbenzamido)-3-(indol-3-yl)propanoate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到(-)-inducamide B
  参考文献：
  名称：

  Synthesis of Inducamides A and B

  摘要：

  The inducamides are a family of chlorinated alkaloids featuring an amide arising from union of an L-tryptophan to a rare chlorosalicylic acid unit, the production of which is linked to a chemically induced mutation in the RNA polymerase of Streptomyces sp. (SNC-109-M3). The synthesis of inducamides A and B has been accomplished by the coupling of 6-hydroxy-3-chloro-2-methylbenzoic acid with L-6-chlorotryptophan and L-tryptophan, respectively, followed by ester hydrolysis. The spectroscopic data and optical rotation for each synthetic sample confirm the structures of these silent secondary metabolites and their biosynthesis from L-tryptophan.

  DOI：

  10.1021/acs.jnatprod.5b00889
• 作为产物：
  描述：

  2-甲氧基-6-甲基苯甲酸甲酯 在 aluminum (III) chloride 、 N-氯代丁二酰亚胺 、 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 158.0h， 生成 (S)-methyl 2-(3-chloro-6-hydroxy-2-methylbenzamido)-3-(indol-3-yl)propanoate
  参考文献：
  名称：

  Synthesis of Inducamides A and B

  摘要：

  The inducamides are a family of chlorinated alkaloids featuring an amide arising from union of an L-tryptophan to a rare chlorosalicylic acid unit, the production of which is linked to a chemically induced mutation in the RNA polymerase of Streptomyces sp. (SNC-109-M3). The synthesis of inducamides A and B has been accomplished by the coupling of 6-hydroxy-3-chloro-2-methylbenzoic acid with L-6-chlorotryptophan and L-tryptophan, respectively, followed by ester hydrolysis. The spectroscopic data and optical rotation for each synthetic sample confirm the structures of these silent secondary metabolites and their biosynthesis from L-tryptophan.

  DOI：

  10.1021/acs.jnatprod.5b00889