2-(4-chloro-2-nitrophenyl)-1H-indole | 65287-40-3

• 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: 2-(4-chloro-2-nitrophenyl)-1H-indole
• CAS: 65287-40-3
• 化学式: C₁₄H₉ClN₂O₂
• 分子量: 272.691
• InChiKey: VNCSRNPGUFVOEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-2-nitrophenyl)-1H-indole 在 sodium hydride 、 三氯氧磷 作用下， 反应 9.0h， 生成 2-(4-Chloro-2-nitro-phenyl)-1-methyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.

  DOI：

  10.1016/0223-5234(93)90036-e
• 作为产物：
  描述：

  1-(4-氯-2-硝基苯)乙酮 在 PPA 、 Polyphosphoric acid (PPA) 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 2-(4-chloro-2-nitrophenyl)-1H-indole
  参考文献：
  名称：

  Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]

  摘要：

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.

  DOI：

  10.1016/0223-5234(93)90036-e

文献信息

• Nitro-Enabled Atroposelective Dynamic Kinetic Resolution of 2-Arylindoles by Phase-Transfer Catalysis
  作者：Chanhee Lee、Sujin Lee、Ahreum Kim、Yongseok Kwon

  DOI：10.1021/acs.orglett.3c03933

  日期：2024.1.26

  This study presents the atroposelective alkylation of 2-arylindoles catalyzed by a substituted cinchonium salt as a phase-transfer catalyst. Under the optimized reaction conditions, various substrates are employed to yield products with high enantioselectivity. The presence of an ortho-nitro group at the aromatic ring is essential for high atroposelectivity, because it facilitates favorable interactions

  本研究提出了由取代的金鸡铵盐作为相转移催化剂催化的 2-芳基吲哚的对转选择性烷基化。在优化的反应条件下，采用多种底物，得到具有高对映选择性的产物。芳环上邻硝基的存在对于高对位选择性至关重要，因为它有利于催化剂和底物之间的良好相互作用。对映选择性的起源揭示了对映体有利的 π-π 相互作用和对不需要的对映体不利的空间张力。
• Cirrincione; Almerico; Diana, Il Farmaco, 1995, vol. 50, # 12, p. 849 - 852
  作者：Cirrincione、Almerico、Diana、Grimaudo、Dattolo、Aiello、Barraja、Mingoia

  DOI：——

  日期：——
• Werbel L. M., Kesten S. J., Turner W. R., Eur. J. Med. Chem, 28 (1993) N 11, S 837-852
  作者：Werbel L. M., Kesten S. J., Turner W. R.

  DOI：——

  日期：——
• Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]
  作者：LM Werbel、SJ Kesten、WR Turner

  DOI：10.1016/0223-5234(93)90036-e

  日期：1993.1

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.