ethyl 1-phenylsulfonylindole-6-carboxylate | 130103-42-3

• 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: ethyl 1-phenylsulfonylindole-6-carboxylate
• 英文别名: Ethyl 1-(benzenesulfonyl)indole-6-carboxylate
• CAS: 130103-42-3
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: LBUBXDIQIKTKKT-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-phenylsulfonylindole-6-carboxylate 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以13%的产率得到1-苯磺酰基-3-碘-1H-吲哚-6-羧酸乙酯
  参考文献：
  名称：

  Novel indole inhibitors of IMPDH from fragments: Synthesis and initial structure–activity relationships

  摘要：

  The elaboration of previously reported indole fragments as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis, in vitro inhibitory values for IMPDH II, PBMC proliferation and physicochemical properties are discussed. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.090
• 作为产物：
  描述：

  6-吲哚甲酸 在 硫酸 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 生成 ethyl 1-phenylsulfonylindole-6-carboxylate
  参考文献：
  名称：

  Novel indole inhibitors of IMPDH from fragments: Synthesis and initial structure–activity relationships

  摘要：

  The elaboration of previously reported indole fragments as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis, in vitro inhibitory values for IMPDH II, PBMC proliferation and physicochemical properties are discussed. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.090

文献信息

• Diels-Alder reactions of 1,5-dihydropyrano[3,4-b]pyrrol-5(1H)-ones, pyrrole-2,3-quinodimethane analogues; a new synthesis of indoles
  作者：P.Mark Jackson、Christopher J. Moody

  DOI：10.1016/s0040-4020(01)90360-6

  日期：1992.9

  The pyrano[3,4-b]pyrrol-5-(1H)-ones 7 are stable cyclic analogues of pyrrole-2,3-quinodimethane, and undergo Diels-Alder reaction with a range of acetylenes (dimethyl acetylenedicarboxylate, ethyl propiolate, ethyl trimethylsilylpropynoate, benzyne and the acetylene equivalent, phenyl vinyl sulfoxide), to give, after loss of carbon dioxide, indoles. The Diels-Alder reaction can be extended to the intramolecular

  吡喃并[3,4- b ]吡咯-5-（1 H）-ones 7是吡咯-2,3-喹二甲烷的稳定环状类似物，并与一定范围的乙炔（乙炔二羧酸二甲酯，丙炔酸乙酯）进行狄尔斯-阿尔德反应，三甲基甲硅烷基丙酸乙酯，苯炔和乙炔当量，苯基乙烯基亚砜），在失去二氧化碳后得到吲哚。Diels-Alder反应可以扩展到分子内变体，得到环烷基-[ e ]-和[ g ]-吲哚。
• JACKSON, P. MARK;MOODY, CHRISTOPHER J., J. CHEM. SOC. PERKIN TRANS. PT. 1,(1990) N, C. 2156-2158
  作者：JACKSON, P. MARK、MOODY, CHRISTOPHER J.

  DOI：——

  日期：——
• Novel indole inhibitors of IMPDH from fragments: Synthesis and initial structure–activity relationships
  作者：Rebekah E. Beevers、George M. Buckley、Natasha Davies、Joanne L. Fraser、Francis C. Galvin、Duncan R. Hannah、Alan F. Haughan、Kerry Jenkins、Stephen R. Mack、William R. Pitt、Andrew J. Ratcliffe、Marianna D. Richard、Verity Sabin、Andrew Sharpe、Sophie C. Williams

  DOI：10.1016/j.bmcl.2006.01.090

  日期：2006.5

  The elaboration of previously reported indole fragments as inhibitors of inosine monophosphate dehydrogenase (IMPDH) is described. The synthesis, in vitro inhibitory values for IMPDH II, PBMC proliferation and physicochemical properties are discussed. (C) 2006 Elsevier Ltd. All rights reserved.