2-(对甲苯肼)-环己酮 | 2257-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(对甲苯肼)-环己酮
• 英文名称: cyclohexane-1,2-dione-mono-p-tolylhydrazone
• 英文别名: Cyclohexan-1,2-dion-mono-p-tolylhydrazon；1-p-Tolylhydrazono-cyclohexanon-(2)；2-[(4-Methylphenyl)hydrazinylidene]cyclohexan-1-one
• CAS: 2257-17-2
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: SVFSFFXAWSSMEM-UHFFFAOYSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  347.7±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  2-(对甲苯肼)-环己酮 生成 6-甲基-2,3,4,9-四氢-1H-咔唑-1-酮
  参考文献：
  名称：

  CAN-SiO2介导的1-酮，1,2,3,4-四氢咔唑的一锅法氧化为咔唑醌：高效合成Murrayaquinone A和koeniginequinone A

  摘要：

  通过CAN-SiO 2介导的反应可以有效地将取代的1-酮-1,2,3,4-四氢咔唑（1）一锅法氧化为咔唑-1,4-醌（2）。该通用方案已成功扩展到两种天然存在的咔唑醌的合成：murrayaquinone A（2b）和koeniginequinone A（2g）。这种新反应的可能机制涉及形成9-羟基-2,3,4,9-四氢-1 H-咔唑-1-酮，然后重排为1-羟基咔唑衍生物，这些衍生物会被铈进一步氧化（IV ）到咔唑醌。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.561
• 作为产物：
  描述：

  p-methylbenzenediazonium chloride 、 Cyclohexanone-2-carbaldehyde 在 乙醇 、 sodium acetate 作用下， 生成 2-(对甲苯肼)-环己酮
  参考文献：
  名称：

  Sen; Ghosh, Journal of the Indian Chemical Society, 1927, vol. 4, p. 484

  摘要：

  DOI：

文献信息

• A novel CAN-SiO2-mediated one-pot oxidation of 1-keto-1,2,3,4-tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and koeniginequinone A
  作者：Suchandra Chakraborty、Gautam Chattopadhyay、Chandan Saha

  DOI：10.1002/jhet.561

  日期：2011.3

  1‐keto‐1,2,3,4‐tetrahydrocarbazoles (1) to carbazole‐1,4‐quinones (2) are efficiently carried out by CAN‐SiO2‐mediated reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9‐hydroxy‐2,3,4,9‐tetrahydro‐1H‐carbazole‐1‐one

  通过CAN-SiO 2介导的反应可以有效地将取代的1-酮-1,2,3,4-四氢咔唑（1）一锅法氧化为咔唑-1,4-醌（2）。该通用方案已成功扩展到两种天然存在的咔唑醌的合成：murrayaquinone A（2b）和koeniginequinone A（2g）。这种新反应的可能机制涉及形成9-羟基-2,3,4,9-四氢-1 H-咔唑-1-酮，然后重排为1-羟基咔唑衍生物，这些衍生物会被铈进一步氧化（IV ）到咔唑醌。J.杂环化​​学。（2011）。
• Synthesis of 2-Hydroxypyrido[2,3-a]-carbazoles and 2-Hydroxypyrimido[4,5-a]carbazoles from 1-Hydroxycarbazoles
  作者：Karnam J. Rajendra Prasad、Kandasamy Shanmugasundaram

  DOI：10.3987/com-99-8587

  日期：——
• Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses
  作者：Kristjan S. Gudmundsson、Paul R. Sebahar、Leah D’Aurora Richardson、John G. Catalano、Sharon D. Boggs、Andrew Spaltenstein、Phiroze B. Sethna、Kevin W. Brown、Robert Harvey、Karen R. Romines

  DOI：10.1016/j.bmcl.2009.05.003

  日期：2009.7

  The synthesis and SAR of a series of substituted 1-aminotetrahydrocarbazoles with potent activity against human papillomaviruses are described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole are outlined and resulting changes in antiviral activity are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the low nanomolar range were identified and (1R)-6-bromo-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazole-1-amine was selected for further evaluation. (C) 2009 Elsevier Ltd. All rights reserved.
• Lions, Journal and Proceedings - Royal Society of New South Wales, 1932, vol. 66, p. 516,524
  作者：Lions

  DOI：——

  日期：——
• Solubility and Metastable Zone Width of 1-Keto-1,2,3,4-tetrahydro-6-methylcarbazole in Acetone
  作者：Patrícia Correia、Carlos Lopes、Manuel E. M. Piedade、João A. A. Lourenço、Maria L. Serrano

  DOI：10.1021/je0600552

  日期：2006.7.1

  The solubility of 1-keto-1,2,3,4-tetrahydro-6-methylcarbazole (KTMC) in acetone in the temperature range from 18 to 55 C was determined by the residue solid technique and the polythermal method using a heat flow calorimeter with turbidity measurement capacities. The results were correlated using a polynomial equation. Utilizing the polythermal method, the metastable zone has also been determined. The broadening of the metastable zone with increasing cooling was observed from 0.05 to 2.0 degrees C center dot min(-1).