2-(10-Methoxy-10H-anthracen-9-ylidene)-malonodinitrile | 169303-61-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(10-Methoxy-10H-anthracen-9-ylidene)-malonodinitrile
• 英文别名: 2-(10-methoxy-10H-anthracen-9-ylidene)propanedinitrile
• CAS: 169303-61-1
• 化学式: C₁₈H₁₂N₂O
• 分子量: 272.306
• InChiKey: IKLBOGSCTNVHFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(10-Methoxy-10H-anthracen-9-ylidene)-malonodinitrile 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以82%的产率得到2-(10-Methoxy-anthracen-9-yl)-malonodinitrile
  参考文献：
  名称：

  2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile: A convenient precursor of 9,10-disubstituted anthracenes

  摘要：

  The acid promoted decomposition of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile in the presence of water, methanol, ethanol, acetic and propionic acid, ethyl thioglycolate, p-thiocresole, and acetyl acetone yielding 9,10-disubstituted 9,10-dihydroanthracenes was investigated. Treatment of the reaction products with tri-ethyl amine followed by hydrochloric acid caused their tautomerization to the corresponding 9,10-disubstituted anthracenes. A mechanism for this:reaction is proposed. The first example of an intermolecular C-C-bond formation during the protic acid promoted decomposition of a diazo compound in the presence of CH-acids was found. An improved procedure for the preparation of the starting diazo compound, which may serve as a convenient precursor of 9,10-disubstituted anthracenes, is described.

  DOI：

  10.1007/bf00807169
• 作为产物：
  描述：

  甲醇 、 2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile 在 硫酸 作用下， 反应 0.33h， 以93%的产率得到2-(10-Methoxy-10H-anthracen-9-ylidene)-malonodinitrile
  参考文献：
  名称：

  2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile: A convenient precursor of 9,10-disubstituted anthracenes

  摘要：

  The acid promoted decomposition of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile in the presence of water, methanol, ethanol, acetic and propionic acid, ethyl thioglycolate, p-thiocresole, and acetyl acetone yielding 9,10-disubstituted 9,10-dihydroanthracenes was investigated. Treatment of the reaction products with tri-ethyl amine followed by hydrochloric acid caused their tautomerization to the corresponding 9,10-disubstituted anthracenes. A mechanism for this:reaction is proposed. The first example of an intermolecular C-C-bond formation during the protic acid promoted decomposition of a diazo compound in the presence of CH-acids was found. An improved procedure for the preparation of the starting diazo compound, which may serve as a convenient precursor of 9,10-disubstituted anthracenes, is described.

  DOI：

  10.1007/bf00807169

文献信息

• Concerning the reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile and related compounds with the cryptohydride system formic acid-triethylamine
  作者：A. F. Vaisburg、A. M. Amer、H. Falk

  DOI：10.1007/bf00807170

  日期：——

  The reaction of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile (1) with the cryptohydride system formic acid - triethylamine was studied. The reaction product turned out to be anthracen-9-yl-acetonitrile (2a) instead of the expected 10-dicyanomethyl-9,10-dihydro-anthracene-9-yl formate. Compounds related to 1 yielded in this reaction the corresponding 10-substituted anthracen-9-yl-acetonitriles. A mechanism of this reaction is proposed. The product of the formic acid promoted decomposition of 1, compound 3b, as well as its tautomer 4b were also obtained.
• 2-(10-Diazo-10H-anthracen-9-ylidene)-malonodinitrile: A convenient precursor of 9,10-disubstituted anthracenes
  作者：A. F. Vaisburg、N. M�ller、H. Falk

  DOI：10.1007/bf00807169

  日期：——

  The acid promoted decomposition of 2-(10-diazo-10H-anthracen-9-ylidene)-malonodinitrile in the presence of water, methanol, ethanol, acetic and propionic acid, ethyl thioglycolate, p-thiocresole, and acetyl acetone yielding 9,10-disubstituted 9,10-dihydroanthracenes was investigated. Treatment of the reaction products with tri-ethyl amine followed by hydrochloric acid caused their tautomerization to the corresponding 9,10-disubstituted anthracenes. A mechanism for this:reaction is proposed. The first example of an intermolecular C-C-bond formation during the protic acid promoted decomposition of a diazo compound in the presence of CH-acids was found. An improved procedure for the preparation of the starting diazo compound, which may serve as a convenient precursor of 9,10-disubstituted anthracenes, is described.