3,3'-dioxo-3,3'-m-phenylene-di-propionic acid dimethyl ester | 75160-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3'-dioxo-3,3'-m-phenylene-di-propionic acid dimethyl ester
• 英文别名: 1,3-Bis-methoxycarbonylacetyl-benzol；3,3'-Dioxo-3,3'-m-phenylen-di-propionsaeure-dimethylester；Methyl 3-[3-(3-methoxy-3-oxopropanoyl)phenyl]-3-oxopropanoate；methyl 3-[3-(3-methoxy-3-oxopropanoyl)phenyl]-3-oxopropanoate
• CAS: 75160-05-3
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: LNXIVJURFWDDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  过氧化苯甲酸叔丁酯 、 3,3'-dioxo-3,3'-m-phenylene-di-propionic acid dimethyl ester 在 copper(II) bis(tetrafluoroborate) 作用下， 以 水 、 氯苯 为溶剂， 反应 2.0h， 以45%的产率得到dimethyl 3,3′-(1,3-phenylene)bis(2-methyl-3-oxopropanoate)
  参考文献：
  名称：

  tert-Butyl Peroxybenzoate-Promoted α-Methylation of 1,3-Dicarbonyl Compounds

  摘要：

  A tert-butyl peroxybenzoate (TBPB)-promoted direct a-methylation of 1,3-dicarbonyl compounds has been developed, providing alpha-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional alpha-methylation of 1,3-dicarbonyl compounds using methyl iodide.

  DOI：

  10.1021/jo502204a
• 作为产物：
  描述：

  m-phenylenedi-propiolic acid dimethyl ester 在 硫酸 作用下， 生成 3,3'-dioxo-3,3'-m-phenylene-di-propionic acid dimethyl ester
  参考文献：
  名称：

  苯间苯二酚和间苯二甲酰苯胺（25. MitteilungüberStickstoff-Heterocyclen）

  摘要：

  DOI：

  10.1002/hlca.193601901127

文献信息

• Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation
  作者：Kevin M. Allan、Boram D. Hong、Brian M. Stoltz

  DOI：10.1039/b913336d

  日期：——

  A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.

  公开了一种方便的方法，可以通过一锅法将β-酮酯合成3-羟基异喹啉和2-羟基-1,4-萘醌，采用芳烯酰基-烷基化/缩合步骤。当与一步法合成β-酮酯底物结合进行时，该方法仅需从商业可得的羧酸起始材料出发，通过两个步骤即可提供这些多芳香结构的新路线。该方法的实用性在于合成了具 atropisomer 的 P,N-配体 QUINAP。
• Über m-Phenylen-di-propiolsäure und m-Di-acetyl-benzol (25. Mitteilung über Stickstoff-Heterocyclen)
  作者：Paul Ruggli、Alfred Staub

  DOI：10.1002/hlca.193601901127

  日期：——
• <i>tert</i>-Butyl Peroxybenzoate-Promoted α-Methylation of 1,3-Dicarbonyl Compounds
  作者：Songjin Guo、Qian Wang、Yan Jiang、Jin-Tao Yu

  DOI：10.1021/jo502204a

  日期：2014.11.21

  A tert-butyl peroxybenzoate (TBPB)-promoted direct a-methylation of 1,3-dicarbonyl compounds has been developed, providing alpha-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional alpha-methylation of 1,3-dicarbonyl compounds using methyl iodide.