methyl<(3-acetyl-4-indolyl)thio>acetate | 83561-15-3

• 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: methyl<(3-acetyl-4-indolyl)thio>acetate
• 英文别名: 3-acetyl-4-(methoxycarbonylmethylthio)indole；methyl ((3-acetyl-4-indolyl)thio)acetate；Methyl [(3-acetyl-1H-indol-4-yl)sulfanyl]acetate；methyl 2-[(3-acetyl-1H-indol-4-yl)sulfanyl]acetate
• CAS: 83561-15-3
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: HCONFRKQHORACX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl<(3-acetyl-4-indolyl)thio>acetate 在 palladium on activated charcoal ammonium acetate 、 氢气 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 methyl 3-(1H-indol-3-yl)butanoate
  参考文献：
  名称：

  Synthetic studies in the indole series. Preparation of the unique antibiotic alkaloid chuangxinmycin by a nitro group displacement reaction

  摘要：

  DOI：

  10.1021/ja00390a037
• 作为产物：
  描述：

  2,6-二硝基甲苯 在 Pd/C sulfided catalyst 盐酸 、 lithium hydroxide 、 氢气 、 四氯化锡 、 氯化铵 作用下， 以 六甲基磷酰三胺 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 79.33h， 生成 methyl<(3-acetyl-4-indolyl)thio>acetate
  参考文献：
  名称：

  Synthetic studies in the indole series. Preparation of the unique antibiotic alkaloid chuangxinmycin by a nitro group displacement reaction

  摘要：

  DOI：

  10.1021/ja00390a037

文献信息

• Transition metal mediated thiation of aromatic rings
  作者：Michael J. Dickens、John P. Gilday、Timothy J. Mowlem、David A. Widdowson

  DOI：10.1016/s0040-4020(01)82405-4

  日期：1991.9

  Three approaches to aromatic thiation have been studied. Dependent upon access to the necessary starting material, displacement of halogen in haloarenetricarbonylchromium(0) complexes by nucleophilic sulphur, quenching of lithiated arenetricarbonylchromium(0) complexes by electrophilic sulphur or palladium catalysed cross coupling of aryl iodides with alkylthiotrialkylstannanes were all effective and

  研究了三种芳族硫杂化方法。取决于获得必要原料的可能性，亲核硫取代卤代芳基三羰基铬（0）络合物中的卤素，亲电硫或钯催化的芳基碘化物与烷基硫代三烷基锡烷的交叉偶联猝灭锂化的芳基羰基铬（0）络合物都是有效的，并且显然在一般情况下范围。后者是首选过程。
• Nitration of 3-acylindoles in the presence of metal MeCN solvates and synthesis of the antibiotic alkaloid chuangxinmycin.
  作者：MASAYUKI MURASE、TAKESHI KOIKE、YUKARI MORIYA、SEISHO TOBINAGA

  DOI：10.1248/cpb.35.2656

  日期：——

  Nitration of 3-acylindoles in the presence of MeCN solvates of Cu2+, Al3+, and Fe2+ salts yielded 3-nitroindole, 4-nitro-and 6-nitro-3-acylindoles, of which 3-acetyl-4-nitroindole was subsequently transformed into dehydrochuangxinmycin (7), the dehydro derivative of the antibiotic alkaloid chuangxinmycin (2).

  在 Cu2+、Al3+ 和 Fe2+ 盐的 MeCN 溶剂存在下硝化 3-酰基吲哚，可得到 3-硝基吲哚、4-硝基和 6-硝基-3-酰基吲哚，其中 3-乙酰基-4-硝基吲哚随后转化为脱氢川霉素（7），即抗生素生物碱川霉素（2）的脱氢衍生物。
• The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase
  作者：Murray J. Brown、Paul S. Carter、Ashley E. Fenwick、Andrew P. Fosberry、Dieter W. Hamprecht、Martin J. Hibbs、Richard L. Jarvest、Lucy Mensah、Peter H. Milner、Peter J. O'Hanlon、Andrew J. Pope、Christine M. Richardson、Andrew West、David R. Witty

  DOI：10.1016/s0960-894x(02)00604-2

  日期：2002.11

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Total synthesis of the unique indole alkaloid chuangxinmycin. Application of nitro group displacement reactions in organic synthesis
  作者：Alan P. Kozikowski、Michael N. Greco

  DOI：10.1021/ja00523a044

  日期：1980.1
• MURASE, MASAYUKI;KOIKE, TAKESHI;MORIYA, YUKARI;TOBINAGA, SEISHO, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2656-2660
  作者：MURASE, MASAYUKI、KOIKE, TAKESHI、MORIYA, YUKARI、TOBINAGA, SEISHO

  DOI：——

  日期：——