9,10-蒽二酮,1-氨基-2-(苯基乙炔基)- | 115057-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9,10-蒽二酮,1-氨基-2-(苯基乙炔基)-
• 英文名称: 1-Amino-2-phenylethynylanthraquinone
• 英文别名: 9,10-Anthracenedione, 1-amino-2-(phenylethynyl)-；1-amino-2-(2-phenylethynyl)anthracene-9,10-dione
• CAS: 115057-71-1
• 化学式: C₂₂H₁₃NO₂
• 分子量: 323.351
• InChiKey: CNVOMYLAPARHAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,10-蒽二酮,1-氨基-2-(苯基乙炔基)- 在 盐酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以78%的产率得到3-Benzoyl-1H-naphtho[2,3-g]indazole-6,11-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1007/bf02495357
• 作为产物：
  描述：

  copper(I) phenylacetylenide 、 1-amino-2-iodo-9,10-anthraquinone 以 吡啶 为溶剂， 反应 2.5h， 以54%的产率得到9,10-蒽二酮,1-氨基-2-(苯基乙炔基)-
  参考文献：
  名称：

  Heterocyclization of o-aminoacetylenylanthraquinones

  摘要：

  DOI：

  10.1007/bf00957311

文献信息

• 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.
• Cyclization of N-(2-R-1-anthraquinonyl)ureas to anthrapyrimidine derivatives
  作者：V. A. Savel'ev、V. A. Loskutov

  DOI：10.1007/bf00472511

  日期：1991.6
• SHVARTSBERG, M. S.;MOROZ, A. A.;PISKUNOV, A. V.;BUDZINSKAYA, I. A., IZV. AN CCCP. CEP. XIM.,(1987) N 11, 2517-2523
  作者：SHVARTSBERG, M. S.、MOROZ, A. A.、PISKUNOV, A. V.、BUDZINSKAYA, I. A.

  DOI：——

  日期：——
• Heterocyclization of o-aminoacetylenylanthraquinones
  作者：M. S. Shvartsberg、A. A. Moroz、A. V. Piskunov、I. A. Budzinskaya

  DOI：10.1007/bf00957311

  日期：1987.11
• 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.