4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]-carbazol-6-one | 91622-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]-carbazol-6-one
• 英文别名: 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one；4-hydroxy-5-phenylpyrido[3,2,1-jk]carbazol-6-one；Phenylmalonylcarbazol；HPPCO；4-hydroxy-3-phenyl-1-azatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one
• CAS: 91622-74-1
• 化学式: C₂₁H₁₃NO₂
• 分子量: 311.34
• InChiKey: AWYXUZHAOIWLOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]-carbazol-6-one 在 磺酰氯 作用下， 以 1,4-二氧六环 为溶剂， 以81%的产率得到5-chloro-5-phenyl-4H-pyrido[3,2,1-jk]carbazole-4,6(5H)-dione
  参考文献：
  名称：

  吡啶并[3,2,1-jk]咔唑-4,6-二酮的合成与反应

  摘要：

  由咔唑和烷基丙二酸或芳基丙二酸酯合成的Pyrido [3,2,1– jk ]咔唑1在位置5发生区域选择性亲电取代反应，例如氯化成5-氯衍生物2，硝化成5-硝基化合物3或羟基化5羟基衍生物4。5-羟基化合物4介绍了用强碱环收缩处理，以5，6或开环产物7。氯基团的交换在2与叠氮或胺，得到相应的叠氮化物8和5-氨基衍生物9和10。的烷基化1与苄基氯或烯丙基溴导致了5-C-烷基化产物的形成11与4-烷氧基衍生物一起12。J. Heterocyclic Chem。，48，1039（2011）。

  DOI：

  10.1002/jhet.600
• 作为产物：
  描述：

  咔唑 、 苯基丙二酸二乙酯 反应 2.5h， 以90%的产率得到4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]-carbazol-6-one
  参考文献：
  名称：

  吡啶并[3,2,1- jk ]咔唑-6-一的合成和闭环反应†

  摘要：

  由咔唑1和丙二酸酯2或3获得的4-羟基-5-苯基吡啶并[3,2,1- jk ]咔唑-6-一（4，5）被转化为反应性中间体，例如4-氯化物9或4-tosylates 10，这又得到4-azido-5-phenyl衍生物11。不能以此方式获得5-烷基-4-叠氮化物11。然而，从4-羟基衍生物4开始开发了一种新的一锅叠氮化反应，其以良好的产率得到了叠氮化物11。4-叠氮基-5-苯基衍生物11f在热解后环化为吲哚12。通过热分析方法（DSC）研究了叠氮化物11的热行为。

  DOI：

  10.1002/jhet.5570420112

文献信息

• Synthesis and ring closure reactions of pyrido[3,2,1-<i>jk</i>]carbazol-6-ones
  作者：Hoai V. Dang、Bernd Knobloch、Nargues S. Habib、Thomas Kappe、Wolfgang Stadlbauer

  DOI：10.1002/jhet.5570420112

  日期：2005.1

  4-Hydroxy-5-phenylpyrido[3,2,1-jk]carbazol-6-ones (4, 5), which were obtained from carbazoles 1 and malonates 2 or 3, were converted to reactive intermediates such as 4-chlorides 9 or 4-tosylates 10, which gave in turn 4-azido-5-phenyl derivatives 11. 5-Alkyl-4-azides 11 were not obtained in this manner; however a new one-pot azidation reaction was developed starting from 4-hydroxy derivatives 4 which

  由咔唑1和丙二酸酯2或3获得的4-羟基-5-苯基吡啶并[3,2,1- jk ]咔唑-6-一（4，5）被转化为反应性中间体，例如4-氯化物9或4-tosylates 10，这又得到4-azido-5-phenyl衍生物11。不能以此方式获得5-烷基-4-叠氮化物11。然而，从4-羟基衍生物4开始开发了一种新的一锅叠氮化反应，其以良好的产率得到了叠氮化物11。4-叠氮基-5-苯基衍生物11f在热解后环化为吲哚12。通过热分析方法（DSC）研究了叠氮化物11的热行为。
• Amination of pyrido[3,2,1-<i>jk</i>]carbazol-6-ones
  作者：Hoai V. Dang、Wolfgang Stadlbauer

  DOI：10.1002/jhet.5570430110

  日期：2006.1

  Amination of 4-hydroxypyridocarbazolones 1 with aniline or benzylamine gave in good yields 4-amines 3. With piperidine in a sealed tube from 4-hydroxy- or 4-chloro-5-alkylpyridocarbazolones 1 or 4 ring opened 1-acylcarbazoles 5 were obtained. Only 4-hydroxy-5-phenyl-pyridocarbazolone 1d gave 4-amines 6. Reduction of 4-azidopyridocarbazolones 7 either by catalytic hydrogenation or in a 2-step synthesis

  用苯胺或苄胺将4-羟基吡啶并咔唑酮1胺化，得到4-胺3的产率很高。用哌啶在密封管中从4-羟基-或4-氯-5-烷基吡啶并咔唑酮1或4开环得到1-酰基咔唑5。仅4-羟基-5-苯基-吡啶并咔唑酮1d给出4-胺6。通过催化氢化或在两步合成中通过磷腈8还原4-叠氮吡啶并咔唑酮7得到4-氨基吡啶并咔唑酮9。胺9也可从苄胺3中获得通过催化脱苄基作用。4-羟基-5- phenylpyridocarbazolone的一个步骤胺化1D 通过脱苄基化至9d中是通过用苄基氯化铵反应观察到。在升高的温度下，从1d开始形成高度熔融的6,13b-二氮杂茚并[1,2,3- hi ] chrysenone 10。
• Synthese von Indolen und Isochinolonen aus Phenylmalonylheterocyclen
  作者：Wolfgang Stadlbauer、Thomas Kappe

  DOI：10.1007/bf00810008

  日期：1984.4
• Structural and photophysical properties of HPPCO (4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one) derivatives
  作者：Yong-Kwang Jeong、Min-Ah Kim、Hyo-Sung Lee、Jong-Moon Kim、Sung Woo Lee、Jun-Gill Kang

  DOI：10.1016/j.saa.2014.06.077

  日期：2015.1

  Proton-substitution effects of 4-hydroxy-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-6-one (HPPCO) on structural and photophysical properties were presented. HPPCO crystallized in the orthorhombic space group Pbca with an intermolecular hydrogen bonding between OH and oxygen atom of the carbonyl. The proton-substituted derivatives, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl acetate (OPPCA) and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jklcarbazol-4-yl benzoate (OPPCB), crystallized in the monoclinic P2(1)/c space group. For OPPCA and OPPCB, a weak interaction between carbonyl oxygen atom in the substituted group and carbon atom in the fused ring was responsible for three-dimensional arrangements. In addition, 6-oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl furan-2-carboxylate (OPPCF), and 6-oxo-5-phenyl-6H-pyrido[3,2,1-jkicarbazol-4-yl naphthoate (OPPCN) were also synthesized. HPPCO and the four derivatives excited by ultraviolet (UV) light produced blue emission. Proton substitution of the OH group significantly increased the radiative transitions and moderately decreased the non-radiative transitions. Consequently the luminescence quantum yields of the derivatives enhanced more than 4.6-fold, no matter what the groups were substituted. Structural and optical properties were further determined using density functional theory (DFT) and ZINDO calculations. The planar structure of the pyridocarbazole-fused ring resulted in pi-pi* electronic transitions within the main frame, with an additional transition from the n(O) of carbonyl to the pi* of the main frame. The three excited states that arose from these transitions were responsible for the blue luminescence. (C) 2014 Elsevier B.V. All rights reserved.
• Structural and Luminescence Properties of 6-Oxo-5-phenyl-6H-pyrido[3,2,1-jk]carbazol-4-yl thiophene-2-carboxylate
  作者：Yong-Kwang Jeong、Min-Ah Kim、Hyo-Sung Lee、Sung Woo Lee、Jun-Gill Kang

  DOI：10.5012/bkcs.2014.35.10.3111

  日期：2014.10.20