3,3',4,4'-Tetrakis(isopentyloxy)benzil | 153399-67-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,3',4,4'-Tetrakis(isopentyloxy)benzil
• 英文别名: 1,2-Bis[3,4-bis(3-methylbutoxy)phenyl]ethane-1,2-dione
• CAS: 153399-67-8
• 化学式: C₃₄H₅₀O₆
• 分子量: 554.767
• InChiKey: GCWRFDIMSBQHRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3',4,4'-Tetrakis(isopentyloxy)benzil 在 三氟代氧化钒(V) 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到2,3,6,7-Tetrakis(isopentyloxy)phenanthrene-9,10-dione
  参考文献：
  名称：

  Synthesis of alkyl- and alkoxy-substituted benzils and oxidative coupling to tetraalkoxyphenanthrene-9,10-diones

  摘要：

  Intermolecular Friedel-Crafts acylation of various substituted alkyl- or alkoxybenzenes with oxalyl chloride using carbon disulfide as solvent gave rise to the benzils 1a-k. Subsequent intramolecular oxidative coupling with either thallium(III) oxide/trifluoroacetic acid or vanadium(V) oxyfluoride/boron trifluoride diethyl etherate resulted in the corresponding phenanthrene-9,10-diones 2a-d. It has been shown that oxygen functionalities at the 3, 3', 4, and 4' positions are necessary for coupling to occur. These substituted benzils and phenanthrene-9,10-diones constitute precursors for ligands in the field of discotic metallomesogens or polymeric mesogens.

  DOI：

  10.1021/jo00082a022
• 作为产物：
  描述：

  邻苯二酚 在 三氯化铝 、 potassium carbonate 作用下， 以 二硫化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3,3',4,4'-Tetrakis(isopentyloxy)benzil
  参考文献：
  名称：

  Synthesis of alkyl- and alkoxy-substituted benzils and oxidative coupling to tetraalkoxyphenanthrene-9,10-diones

  摘要：

  Intermolecular Friedel-Crafts acylation of various substituted alkyl- or alkoxybenzenes with oxalyl chloride using carbon disulfide as solvent gave rise to the benzils 1a-k. Subsequent intramolecular oxidative coupling with either thallium(III) oxide/trifluoroacetic acid or vanadium(V) oxyfluoride/boron trifluoride diethyl etherate resulted in the corresponding phenanthrene-9,10-diones 2a-d. It has been shown that oxygen functionalities at the 3, 3', 4, and 4' positions are necessary for coupling to occur. These substituted benzils and phenanthrene-9,10-diones constitute precursors for ligands in the field of discotic metallomesogens or polymeric mesogens.

  DOI：

  10.1021/jo00082a022

文献信息

• Synthesis of alkyl- and alkoxy-substituted benzils and oxidative coupling to tetraalkoxyphenanthrene-9,10-diones
  作者：Bernhard Mohr、Volker Enkelmann、Gerhard Wegner

  DOI：10.1021/jo00082a022

  日期：1994.2

  Intermolecular Friedel-Crafts acylation of various substituted alkyl- or alkoxybenzenes with oxalyl chloride using carbon disulfide as solvent gave rise to the benzils 1a-k. Subsequent intramolecular oxidative coupling with either thallium(III) oxide/trifluoroacetic acid or vanadium(V) oxyfluoride/boron trifluoride diethyl etherate resulted in the corresponding phenanthrene-9,10-diones 2a-d. It has been shown that oxygen functionalities at the 3, 3', 4, and 4' positions are necessary for coupling to occur. These substituted benzils and phenanthrene-9,10-diones constitute precursors for ligands in the field of discotic metallomesogens or polymeric mesogens.