Ethyl 1-[(2-nitrophenyl)methyl]indole-2-carboxylate | 99384-70-0

• 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-[(2-nitrophenyl)methyl]indole-2-carboxylate
• CAS: 99384-70-0
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: ZUDUARBUDDQRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-[(2-nitrophenyl)methyl]indole-2-carboxylate 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以72%的产率得到吲哚-2-羧酸乙酯
  参考文献：
  名称：

  o-Nitrobenzyl as a photocleavable nitrogen protecting group for indoles, benzimidazole, and 6-chlorouracil

  摘要：

  The potential for the o-nitrobenzyl group as an alternative nitrogen protecting group for various indoles, benzimidazole, and 6-chlorouracil was determined. Treatment of the appropriate N-H containing substrate with LiH or NaH in DMF followed by o-nitrobenzyl bromide afforded reasonable yields of N-alkylated products. To effect removal of this group, simple photolysis with 300 nm light afforded good yields of starting substrate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10600-1
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 、 2-硝基苄溴 在 lithium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到Ethyl 1-[(2-nitrophenyl)methyl]indole-2-carboxylate
  参考文献：
  名称：

  o-Nitrobenzyl as a photocleavable nitrogen protecting group for indoles, benzimidazole, and 6-chlorouracil

  摘要：

  The potential for the o-nitrobenzyl group as an alternative nitrogen protecting group for various indoles, benzimidazole, and 6-chlorouracil was determined. Treatment of the appropriate N-H containing substrate with LiH or NaH in DMF followed by o-nitrobenzyl bromide afforded reasonable yields of N-alkylated products. To effect removal of this group, simple photolysis with 300 nm light afforded good yields of starting substrate. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10600-1

文献信息

• Indolo[2,1-c][1,4]benzodiazepines: a new class of antiallergic agents
  作者：Chih Y. Ho、William E. Hageman、Francis J. Persico

  DOI：10.1021/jm00156a034

  日期：1986.6

  A series of 12-(cyclic alkylamino)-6H-indolo[2,1-c][1,4]benzodiazepines were synthesized that possess antihistamine and antiserotonin activities as well as ability to inhibit mediator release. Compound 6a, 12-(4-methyl-1-piperazinyl)-6H-indolo[2,1-c][1,4]benzodiazepine was a more potent inhibitor of serotonin release than disodium cromoglycate (DSCG) and ketotifen and approximately equivalent to oxatomide

  合成了一系列具有抗组胺和抗5-羟色胺活性以及抑制介质释放能力的12-（环烷基氨基）-6H-吲哚并[2,1-c] [1,4]苯并二氮杂s。化合物6a，12-（4-甲基-1-哌嗪基）-6H-吲哚并[2,1-c] [1,4]苯并二氮杂卓比色甘酸二钠（DSCG）和酮替芬更有效地抑制5-羟色胺释放到草酮。在体内测试（PCA和ALA）中，化合物6a等同于或优于DSCG和草酮。这些药物具有治疗多种过敏性疾病的潜力。
• HO, CHIH, Y.
  作者：HO, CHIH, Y.

  DOI：——

  日期：——
• HO, CHIH, Y.;HAGEMAN, W. E.;PERSICO, F. J., J. MED. CHEM., 1986, 29, N 6, 1118-1121
  作者：HO, CHIH, Y.、HAGEMAN, W. E.、PERSICO, F. J.

  DOI：——

  日期：——