5,6,11,12-tetrahydroindolo[2,3-a]carbazole | 22298-61-9

• 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: 5,6,11,12-tetrahydroindolo[2,3-a]carbazole
• 英文别名: 5,6-dihydroindolocarbazole；5,6,11,12-Tetrahydro-indolo<2,3-a>carbazol；5,6,11,12-Tetrahydro-indolo[2,3-a]carbazol
• CAS: 22298-61-9
• 化学式: C₁₈H₁₄N₂
• 分子量: 258.323
• InChiKey: MQNWFUGVDDIMNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  535.4±30.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,3,4,9-四氢-1H-咔唑-1-酮 、 苯肼 在 溶剂黄146 作用下， 反应 3.0h， 以69%的产率得到5,6,11,12-tetrahydroindolo[2,3-a]carbazole
  参考文献：
  名称：

  Synthesis, characterization and pharmacological activities of 5,6,11,12-tetrahydroindolo[2,3-a]carbazole derivatives

  摘要：

  A series of new 5,6,11,12-tetrahydroindolo[2,3-a]carbazole derivatives (3a-h) was synthesized. Treatment of 8-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole (1a) with phenylhydrazine hydrochloride in ethanol furnished the title compound (3a) in poor yield along with 8-methyl-1-phenylhydrazono-1,2,3,4-tetrahydrocarbazole (2a). Better yields were obtained when la-h were treated with phenylhydrazine in glacial acetic acid. All the newly synthesized compounds were characterized on the basis of IR, NMR, mass-spectra and elemental analysis and screened for pharmacological activities. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01035-7

文献信息

• A diversity-oriented approach to indolocarbazoles via Fischer indolization and olefin metathesis: total synthesis of tjipanazole D and I
  作者：Sambasivarao Kotha、Mohammad Saifuddin、Vikas R. Aswar

  DOI：10.1039/c6ob01679k

  日期：——

  Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels–Alder reaction have been used as key steps. Diverse strategies demonstrated

  已经报道了在绿色条件下使用L -（+）-酒石酸和N，N-二甲基尿素通过费歇尔吲哚化的两倍进行合成吲哚并咔唑的新策略。从一种台式起始原料环己酮开始，该方法已扩展到天然产物的合成，如替帕帕唑D和I，以及紫杉醇和消旋素B的核心结构。。在这里，诸如闭环复分解，烯炔复分解和Diels–Alder反应之类的原子经济反应已被用作关键步骤。此处展示的多种策略在药物化学和材料科学中用于设计修饰的吲哚文库是有用的。
• Accurate Method To Quantify Binding in Supramolecular Chemistry
  作者：Kristjan Haav、Sandip A. Kadam、Lauri Toom、Philip A. Gale、Nathalie Busschaert、Marco Wenzel、Jennifer R. Hiscock、Isabelle L. Kirby、Tõiv Haljasorg、Märt Lõkov、Ivo Leito

  DOI：10.1021/jo400626p

  日期：2013.8.16

  measurement of the binding strength of 28 synthetic anion receptors toward acetate in acetonitrile containing 0.5% water. The receptors included differently substituted indolocarbazoles, ureas, thioureas, and some others. Possible deprotonation of more acidic receptors of each compound class by acetate was checked by measuring their acidities (ΔpKa values) relative to acetic acid in the same solvent. A

  （Δlog对于主客体结合亲和力的准确和可比较的测量的方法被引入，由此在结合强度差异ķ屁股值是在相同的溶剂条件下，朝着特定客体的两个主体分子之间测量的。测量差异而不是绝对值能够获得高度准确的结果，因为许多不确定性源（溶液中客体的溶剂化/缔合状态，溶剂组成的偏差等）被抵消了。作为概念的证明，该方法用于测量28种合成阴离子受体与含0.5％水的乙腈中的乙酸盐的结合强度。受体包括不同取代的吲哚并咔唑，脲，硫脲等。由醋酸各化合物类的酸性更强的受体可能去质子化，通过测定其酸度（ΔP检查ķ一个相对于相同溶剂中的乙酸的值）。从结果构建了大约2.7 log个单位的自洽（一致性标准偏差为0.04 log个单位）结合亲和力标度。绝对日志ķ屁股通过锚定规模的绝对日志中发现的值ķ屁股2个受体分子的值，通过直接测量独立地确定。预期这种新方法可用于精确定量与超分子化学有关的各种结合过程。
• Synthesis, characterization and pharmacological activities of 5,6,11,12-tetrahydroindolo[2,3-a]carbazole derivatives
  作者：R Balamurali、K.J Rajendra Prasad

  DOI：10.1016/s0014-827x(01)01035-7

  日期：2001.4

  A series of new 5,6,11,12-tetrahydroindolo[2,3-a]carbazole derivatives (3a-h) was synthesized. Treatment of 8-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole (1a) with phenylhydrazine hydrochloride in ethanol furnished the title compound (3a) in poor yield along with 8-methyl-1-phenylhydrazono-1,2,3,4-tetrahydrocarbazole (2a). Better yields were obtained when la-h were treated with phenylhydrazine in glacial acetic acid. All the newly synthesized compounds were characterized on the basis of IR, NMR, mass-spectra and elemental analysis and screened for pharmacological activities. (C) 2001 Elsevier Science S.A. All rights reserved.