2-acetylamino-9-acetylcarbazole | 77229-05-1

• 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-acetylamino-9-acetylcarbazole
• 英文别名: acetamido-2 acetyl-9 carbazole；2-Acetamido-9-acetylcarbazole；N-(9-acetylcarbazol-2-yl)acetamide
• CAS: 77229-05-1
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: OPSIAGUGFKPTAP-UHFFFAOYSA-N

物化性质

• 熔点：
  232-233 °C
• 沸点：
  475.3±27.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetylamino-9-acetylcarbazole 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.5h， 以78%的产率得到9H-咔唑-2-胺
  参考文献：
  名称：

  2-氨基咔唑合成

  摘要：

  DOI：

  10.1016/0040-4020(80)88027-6
• 作为产物：
  描述：

  2-乙酰基咔唑 在 盐酸 、 盐酸羟胺 、 boron trifluoride diacetate 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 3.83h， 生成 2-acetylamino-9-acetylcarbazole
  参考文献：
  名称：

  2-氨基咔唑合成

  摘要：

  DOI：

  10.1016/0040-4020(80)88027-6

文献信息

• Pyrrolo(1',2':1,2)pyrazino(6,5-b)carbazoles.
  作者：JEAN-CHARLES LANCELOT、JEAN-MARIE GAZENGEL、SYLVAIN RAULT、MAX ROBBA

  DOI：10.1248/cpb.31.45

  日期：——

  The synthesis of the new heterocycles pyrrolo [1', 2' : 1, 2] pyrazino [6, 5-b] carbazoles was achieved by the intramolecular cyclisation of 2-(1-pyrrolyl) carbazole derivatives. These latter compounds were obtained by the Clauson-Kaas reaction starting from the corresponding 2-aminocarbazoles, obtained by reduction of 2-nitrocarbazoles. A study of this reduction has shown that the introduction of acetyl grouping in position 9 makes this reaction easier and gives better results than previous methods. 1H-NMR spectra are studied.

  新杂环吡咯 [1', 2' : 1, 2] 吡嗪并 [6, 5-b] 咔唑的合成是通过 2-(1-吡咯基) 咔唑衍生物的分子内环化反应实现的。后一种化合物是通过克劳森-卡斯反应从相应的 2-氨基咔唑（由 2-硝基咔唑还原而成）获得的。对该还原反应的研究表明，在第 9 位引入乙酰基使该反应更容易进行，并比以前的方法得到更好的结果。对 1H-NMR 光谱进行了研究。
• Keratin Dyeing Compounds, Keratin Dyeing Compositions Containing Them, And Use Thereof
  申请人：Glenn Wayne Robert

  公开号：US20080098535A1

  公开（公告）日：2008-05-01

  Compositions for the oxidative dyeing of keratin fibers, comprising a medium suitable for dyeing and one or more tricyclic fused 6-5-6 heteroaromatic keratin dyeing compounds having one heteroatom. A method for oxidative dyeing of keratin fibers, comprising applying such compositions in the presence of an oxidizing agent, for a period sufficient to develop the desired coloration.

  含氧化染料的角蛋白纤维氧化染色组合物，包括适于染色的介质和一个或多个三环融合6-5-6杂环角蛋白染料化合物，其中含有一个杂原子。一种氧化染色角蛋白纤维的方法，包括在氧化剂存在下应用这种组合物，以达到所需的着色时间。
• KYZIOL J. B.; LYZNIAK A., TETRAHEDRON, 1980, 36, NO 20-21, 3017-3019
  作者：KYZIOL J. B.、 LYZNIAK A.

  DOI：——

  日期：——
• LANCELOT, J. -C.;GAZENGEL, J. -M.;RAULT, S.;ROBBA, M., CHEM. AND PHARM. BULL., 1983, 31, N 1, 45-51
  作者：LANCELOT, J. -C.、GAZENGEL, J. -M.、RAULT, S.、ROBBA, M.

  DOI：——

  日期：——
• Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. II. Ortho-aminonitro derivatives of 9H-carbazole
  作者：V. André、C. Boissart、F. Sichel、P. Gauduchon、J.Y. Le Talaër、J.C. Lancelot、M. Robba、C. Mercier、S. Chemtob、E. Raoult、A. Tallec

  DOI：10.1016/0165-1218(95)90066-7

  日期：1995.11

  The mutagenicity of 4 ortho-aminonitrocarbazoles and 2 ortho-acetamidonitrocarbazoles was assayed in Salmonella strains TA1538, TA98, TA100, TA1537 and TA1977 and in nitroreductase and acetylase deficient strains TA98NR and TA98/1,8DNP(6), with and without S9 from phenobarbital-induced rat liver. Mutagenicity of these compounds and of their monosubstituted precursors (Andre et al., Mutation Res. 299 (1993) 63-73) was tentatively correlated with various molecular descriptors. The hydrophobicity appears as an important determinant of direct mutagenicity in this series of closely related nitrocarbazoles, with a general trend of increasing mutagenicity with an increase of hydrophobicity. On the contrary; the ease of nitroreduction (depicted by electrochemical reduction potential and energy of the lowest unoccupied molecular orbitals) does not appear as a major direct determinant. The ortho-amino group does not favour mutagenic potential, except for 1-nitro-2-aminocarbazole, which is the most potent direct mutagen. Mutagenicity in the presence of S9 is attributed mainly to amine metabolism, Hydrophobicity has only a limited effect on this activity, whereas an unexpected positive correlation is found with electrochemical oxidation potential. The influence of reciprocal electronic delocalization effects of nitro and amino groups, through the modulation of the ultimate mutagenic species (nitrenium ion) reactivity, is also discussed.