1-(2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole | 608513-04-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
• 英文别名: 1-(2-nitrophenyl)-4,9-dihydro-3H-β-carboline；1-(2-nitrophenyl)-3,4-dihydro-β-carboline；4,9-Dihydro-1-(2-nitrophenyl)-3H-pyrido[3,4-b]indole
• CAS: 608513-04-8
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: NAORZWZZSCWCNT-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  509.6±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3,13-dihydro-7H-indazolo[3,2-a]-β-carboline-5N-oxide
  参考文献：
  名称：

  Synthesis of New β-Carboline Derivatives via 1,7-Electrocyclisation of Azomethine Ylides

  摘要：

  通过对易于获得的δ-咔啉衍生物中的偶氮甲基酰化物进行 1,7 双极电环化反应，开发出了一条通向苯并[5,6]氮杂卓[2,1-a]-δ-咔啉和吲唑并[3,2-a]-δ-咔啉环系统的新途径。

  DOI：

  10.1055/s-2006-926400
• 作为产物：
  描述：

  邻硝基苯甲酸 在 phosphorus pentoxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成 1-(2-nitrophenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation

  摘要：

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.

  DOI：

  10.1021/ol053033y

文献信息

• Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M
  作者：Sunil Gaikwad、Dayanand Kamble、Pradeep Lokhande

  DOI：10.1016/j.tetlet.2018.04.043

  日期：2018.6

  Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines, using molecular I2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-β-carbolines and β-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M.

  在DMSO溶剂中使用分子I 2和H 2 O 2对四氢-β-咔啉进行温度控制的化学选择性脱氢和芳构化，可分别实际获得一系列相应的3,4-二氢-β-咔啉和β-咔啉。该方法已成功用于Kumujian-C，Eudistomin-U，Norharmane Harmane Harmalan和Isoeudistomin-M的短合成中。
• Microwave Assisted Pictet–Spengler and Bischler–Napieralski Reactions
  作者：Bikash Pal、Parasuraman Jaisankar、Venkatachalam S. Giri

  DOI：10.1081/scc-120021516

  日期：2003.1.7

  Abstract Pictet–Spengler and Bischler–Napieralski reaction products have been prepared–using microwave irradiation on silicagel support under solvent free condition. Microwave assisted reactions have resulted in better yields of the desired products than prepared under conventional conditions.

  摘要 Pictet-Spengler 和 Bischler-Napieralski 反应产物已在无溶剂条件下在硅胶载体上使用微波辐射制备。微波辅助反应比在常规条件下制备的所需产物的产率更高。
• An efficient and convenient synthesis of heterocycle-fused indazoles via the N–N bond forming reaction of nitroarenes induced by low-valent titanium reagent
  作者：Wei Lin、Ming-Hua Hu、Xian Feng、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1016/j.tet.2013.05.074

  日期：2013.8

  A mild and efficient one-pot protocol for the preparation of 8,13-dihydro-7H-indolo[2′,3′:3,4]pyrido[1,2-b]indazole and 5,6-dihydroindazolo[3,2-a]isoquinoline via the reductive cyclization of nitro-aryl substrates mediated by a low-valent titanium reagent has been developed. The attractive features of the current method include an N–N bond formation and the selective reduction of the CN bond and nitro

  一种温和有效的一锅法制备8,13-dihydro-7 H-吲哚并[2'，3'：3,4]吡啶并[1,2- b ]吲唑和5,6-二氢吲唑[3]已经开发了通过低价钛试剂介导的硝基-芳基底物的还原环化形成的2-2- α ]异喹啉。当前方法的吸引人的特征包括N–N键的形成以及C N键和硝基的选择性还原，通过控制反应混合物的pH值，一锅即可轻松实现。
• Unprecedented SnCl₂-Mediated Cyclization of Nitro Arenes via N−N Bond Formation
  作者：Devesh Sawant、Rishi Kumar、Prakas R. Maulik、Bijoy Kundu

  DOI：10.1021/ol053033y

  日期：2006.4.1

  A mild, efficient, one-pot protocol for the cyclization of nitro-aryl substrates using SnCl2 has been described. The mechanistic course of the reaction suggests the involvement of a hydroxylamine intermediate leading to an intramolecular cyclization via N-N bond formation. The versatility of the methodology has been demonstrated by using two nitro-aryl substrates derived from dihydroisoquinolines and dihydro-beta-carbolines. The intramolecular cyclization led to the formation of indazoles in high yields and purities.
• Synthesis of New β-Carboline Derivatives via 1,7-Electrocyclisation of Azomethine Ylides
  作者：Miklós Nyerges、Andrea Virányi、Judit Tóth、Gábor Blaskó、László Tőke

  DOI：10.1055/s-2006-926400

  日期：2006.4

  A new route to the benzo[5,6]azepino[2,1-a]-β-carboline and indazolo[3,2-a]-β-carboline ring systems has been developed via the 1,7-dipolar electrocyclisation reactions of azomethine ylides derived from easily available β-carboline derivatives.

  通过对易于获得的δ-咔啉衍生物中的偶氮甲基酰化物进行 1,7 双极电环化反应，开发出了一条通向苯并[5,6]氮杂卓[2,1-a]-δ-咔啉和吲唑并[3,2-a]-δ-咔啉环系统的新途径。