2-methylene-1,4-diphenylbutane-1,4-dione | 89665-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylene-1,4-diphenylbutane-1,4-dione
• 英文别名: 2,3-dibenzoylpropene；2-methylene-1,4-diphenyl-butane-1,4-dione；2-Methylen-1,4-diphenyl-butan-1,4-dion；2-Methylidene-1,4-diphenylbutane-1,4-dione
• CAS: 89665-35-0
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: ZYAYBWXXBGXJMK-UHFFFAOYSA-N

物化性质

• 熔点：
  59.8-60 °C(Solv: ethanol (64-17-5))
• 沸点：
  420.2±45.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylene-1,4-diphenylbutane-1,4-dione 在 盐酸 、 氯仿 作用下， 生成 3-Chloromethyl-2,5-diphenylfuran
  参考文献：
  名称：

  2,3-Dibenzoylpropene. The Addition of Hydrogen Chloride to 1,2-Dibenzoylpropene¹

  摘要：

  DOI：

  10.1021/ja01156a014
• 作为产物：
  描述：

  2-(2-hydroxy-2-phenylcyclopropyl)-1-phenylethan-1-one 在 copper(II) nitrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以73%的产率得到2-methylene-1,4-diphenylbutane-1,4-dione
  参考文献：
  名称：

  Ring-opening of tertiary cyclopropanols derived from β-diketones

  摘要：

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.064

文献信息

• NEW C–C BOND FORMATION WITH PYRIDINIUM METHYLIDE: HYDROMETHYLENATION OF OLEFIN
  作者：Otohiko Tsuge、Shuji Kanemasa、Satoru Kuraoka、Shigeori Takenaka

  DOI：10.1246/cl.1984.281

  日期：1984.2.5

  New C–C bond formation with pyridinium methylide is presented: Pyridinium methylide reacts with electron-deficient olefins providing the next higher homologs of olefins, in which the double bond of starting olefin is saturated and, instead, a C=C double bond is newly formed. This reaction mode has been never reported before in the study of nitrogen ylide and is to be referred to as hydromethylenation

  提出了与甲基化吡啶鎓形成新的 C–C 键：甲基化吡啶鎓与缺电子烯烃反应，提供下一个更高的烯烃同系物，其中起始烯烃的双键饱和，取而代之的是新的 C=C 双键形成。这种反应模式在氮叶立德的研究中从未有过报道，被称为烯烃的加氢甲基化。在碱存在下，发生 1,2-双键迁移，导致起始烯烃的甲基化衍生物。
• Miki, Yasuyoshi; Hachiken, Hiroko; Takemura, Shoji, Heterocycles, 1984, vol. 22, # 4, p. 701 - 703
  作者：Miki, Yasuyoshi、Hachiken, Hiroko、Takemura, Shoji、Ikeda, Masazumi

  DOI：——

  日期：——
• TSUGE, OTOHIKO;KANEMASA, SHUJI;KURAOKA, SATORU;TAKENAKA, SHIGEORI, CHEM. LETT., 1984, N 2, 281-284
  作者：TSUGE, OTOHIKO、KANEMASA, SHUJI、KURAOKA, SATORU、TAKENAKA, SHIGEORI

  DOI：——

  日期：——
• MIKI, YASUYOSHI;HACHIKEN, HIROKO;TAKEMURA, SHOJI;IKEDA, MASAZUMI, HETEROCYCLES, 1984, 22, N 4, 701-703
  作者：MIKI, YASUYOSHI、HACHIKEN, HIROKO、TAKEMURA, SHOJI、IKEDA, MASAZUMI

  DOI：——

  日期：——
• Ring-opening of tertiary cyclopropanols derived from β-diketones
  作者：Le-Zhen Li、Bin Xiao、Qing-Xiang Guo、Song Xue

  DOI：10.1016/j.tet.2006.05.064

  日期：2006.8

  The ring-opening reaction of 1,2-di substituted cyclopropanols, prepared from beta-diketones, mediated by Cu(NO3)(2), p-TsOH, and NaOH is reported. The Cu(II)-mediated ring-opening of cyclopropanols gave alpha-methylene-gamma-diketones in good yields. The reaction took place at the less substituted carbon of the cyclopropanols, involving mild conditions and a simple procedure. The reaction induced by p-TsOH in CH2O2 afforded alpha-methyl-gamma-diketones as the major product with minor amounts of 8-diketones. The 2,3,5-tri substituted furans were obtained in high yields when the ring-opening reaction was mediated by p-TsOH in methanol under reflux conditions. In the presence of sodium hydroxide the reaction proceeded smoothly in preference to the formation of beta-diketones, particularly for substrates with an aromatic group on the cyclopropane. (c) 2006 Elsevier Ltd. All rights reserved.