1-Amino-2-(4,4-dimethyl-3-oxo-pent-1-ynyl)-anthraquinone | 129995-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Amino-2-(4,4-dimethyl-3-oxo-pent-1-ynyl)-anthraquinone
• 英文别名: 9,10-Anthracenedione, 1-amino-2-(4,4-dimethyl-3-oxo-1-pentynyl)-；1-amino-2-(4,4-dimethyl-3-oxopent-1-ynyl)anthracene-9,10-dione
• CAS: 129995-14-8
• 化学式: C₂₁H₁₇NO₃
• mdl: MFCD05258999
• 分子量: 331.371
• InChiKey: ZXQAYVWEYFIIMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Amino-2-(4,4-dimethyl-3-oxo-pent-1-ynyl)-anthraquinone 在 甲酸 、 硫酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 生成 3-(3-tert-Butyl-quinoxalin-2-yl)-1H-naphtho[2,3-g]indazole-6,11-dione
  参考文献：
  名称：

  An unusual direction of the Richter synthesis. 1H-naphtho[2,3-g]indazole-6,11-diones

  摘要：

  Diazotization of 2-acetylenic derivatives of 1-aminoanthraquinone followed by intramolecular cyclization leads to the formation is good yields of 1H-3-acyl- or 1H-3-(1,1-dichloroalkyl)naphtho[2,3-g]indazole-6,11-diones, rather than 3-substituted 4-hydroxynahtho[2,3-h]cinnoline-7,1 2-diones, the normal Richter synthesis products.

  DOI：

  10.1016/s0040-4039(00)73485-x
• 作为产物：
  描述：

  1-amino-2-ethynylanthraquinone 、 三甲基乙酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 作用下， 以 苯 为溶剂， 反应 1.5h， 以86%的产率得到1-Amino-2-(4,4-dimethyl-3-oxo-pent-1-ynyl)-anthraquinone
  参考文献：
  名称：

  The cyclization of vicinal 1-amino-2-acylvinylated derivatives of aromatic amines

  摘要：

  A general method for the synthesis of substituted fused polycyclic compounds containing a 4-alkylamino- or 4-dialkylaminopyridine cycle has been proposed. The method includes the addition of primary or secondary amines to vicinal (acylethynyl)arylamines followed by the cyclization of the adducts under acidic or basic catalysis conditions. Various aminonaphthoquinolinediones and aminoquinolines have been prepared in high yields by this method.

  DOI：

  10.1007/bf00699931

文献信息

• Synthesis of 4-haloquinolines and their fused polycyclic derivatives
  作者：Mark S. Shvartsberg、Ekaterina A. Kolodina

  DOI：10.1016/j.mencom.2008.03.020

  日期：2008.3

  A general method for the synthesis of 4-chloro- or 4-bromo-substituted quinolines and quinoline moieties of polycyclic compounds includes the addition of hydrogen halides to vic-amino(3-oxoalk-1-ynyl)arenes under mild conditions followed by the intramolecular cyclization of the adducts.
• An unusual direction of the Richter synthesis. 1H-naphtho[2,3-g]indazole-6,11-diones
  作者：Mark S. Shvartsberg、Irena D. Ivanchikova、Lidiya G. Fedenok

  DOI：10.1016/s0040-4039(00)73485-x

  日期：1994.9

  Diazotization of 2-acetylenic derivatives of 1-aminoanthraquinone followed by intramolecular cyclization leads to the formation is good yields of 1H-3-acyl- or 1H-3-(1,1-dichloroalkyl)naphtho[2,3-g]indazole-6,11-diones, rather than 3-substituted 4-hydroxynahtho[2,3-h]cinnoline-7,1 2-diones, the normal Richter synthesis products.
• SHVARTSBERG, M. S.;MZHELSKAYA, M. A.;MOROZ, A. A.
  作者：SHVARTSBERG, M. S.、MZHELSKAYA, M. A.、MOROZ, A. A.

  DOI：——

  日期：——
• The cyclization of vicinal 1-amino-2-acylvinylated derivatives of aromatic amines
  作者：M. S. Shvartsberg、A. V. Piskunov、M. A. Mzhel'skaya、A. A. Moroz

  DOI：10.1007/bf00699931

  日期：1993.8

  A general method for the synthesis of substituted fused polycyclic compounds containing a 4-alkylamino- or 4-dialkylaminopyridine cycle has been proposed. The method includes the addition of primary or secondary amines to vicinal (acylethynyl)arylamines followed by the cyclization of the adducts under acidic or basic catalysis conditions. Various aminonaphthoquinolinediones and aminoquinolines have been prepared in high yields by this method.
• Reaction of 1-amino-2-phenylethynyl-and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2. Synthesis of 1H-3-acylnaphtho[2,3-g]indazole-6,11-diones
  作者：I. D. Ivanchikova、L. G. Fedenok、M. S. Shvartsberg

  DOI：10.1007/bf02495357

  日期：1997.1

  The reactions of 1-amino-2-phenylethynyl- and 2-acylethynyl-1-amino-9,10-anthraquinones with HNO2 in a mixture of dioxane and a mineral acid at 20 degrees C were studied. Under these conditions, 2-alkynyl-1-amino-9,10-anthraquinones, irrespective of the structure of the C=CR substituent, are cyclized into 3-substituted 1H-naphtho[2,3-g]indazole-6,11-diones. The nature of the acetylenic group in the initial compound and the choice of the mineral acid determine the structure of the substituent in position 3 of the product (1,1-dichloroalkyl or acyl) but have no effect on the regiospecificity of cyclization.