(E)-1-ethyl 4-hydrogen 2-succinate | 132608-29-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-ethyl 4-hydrogen 2-succinate
• 英文别名: (E)-1-ethyl 4-hydrogen 2-(cyclohexylphenylmethylene)succinate
• CAS: 132608-29-8
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: UHCBGOMXOMZADY-VLGSPTGOSA-N

物化性质

• 沸点：
  465.4±33.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-1-ethyl 4-hydrogen 2-succinate 在 palladium on activated charcoal 三乙烯二胺 、 盐酸 、 sodium periodate 、 dimethyl sulfide borane 、 氢气 、 lithium cyclohexylisopropylamide 作用下， 以 溶剂黄146 为溶剂， 反应 18.67h， 生成 8-cyclohexyl-3,3a,8,8a-tetrahydro-1H-indeno<1,2-c>furan-1-one
  参考文献：
  名称：

  Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-benzylfuran2(5H)-ones; cyclisation to indenofuranones

  摘要：

  The effect of substitution at the 'central methane' on the photoreactivity of 3-benzylfuran-2(5H)ones 5a-g was investigated. Despite its di-pi-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields. Only the substitution by phenyl caused the di-pi-methane rearrangement to give a cyclopropanofuranone 18g in moderate yield.

  DOI：

  10.1039/p19940001833
• 作为产物：
  描述：

  环己基苯基甲酮 、 丁二酸二乙酯 在 sodium hydride 作用下， 以90%的产率得到(E)-1-ethyl 4-hydrogen 2-succinate
  参考文献：
  名称：

  Furan-2(3H)- and 2(5H)-ones. Part 5. Photoreactions of 3-benzylfuran2(5H)-ones; cyclisation to indenofuranones

  摘要：

  The effect of substitution at the 'central methane' on the photoreactivity of 3-benzylfuran-2(5H)ones 5a-g was investigated. Despite its di-pi-methane structure, photochemical arylation was effected to give substituted indenofuranones 6 in good yields. Only the substitution by phenyl caused the di-pi-methane rearrangement to give a cyclopropanofuranone 18g in moderate yield.

  DOI：

  10.1039/p19940001833

文献信息

• Furan-2(3H)- and -2(5H)-ones. Part 6. Di-π-methane rearrangement of the α-substituted 4-benzylfuran-2(5H)-one system
  作者：Osamu Muraoka、Genzoh Tanabe、Mié Higashiura、Toshie Minematsu、Takefumi Momose

  DOI：10.1039/p19950001437

  日期：——

  The effect of the ‘central methane’ substitution on the di-π-methane rearrangement in 4-benzyl-2,5-dihydrofuran-2-ones 8a–d was investigated. Significant enhancement of efficiency in the rearrangement leading in high combined yields to two isomeric products, endo-12 and exo-12, is discussed in terms of both the substituent effects at the benzylic carbon and the restrained features of the ring-enrolled

  研究了“中央甲烷”取代对4-苄基-2,5-二氢呋喃-2-酮8a - d中二-π-甲烷重排的影响。讨论了重排效率的显着提高，导致高收率合成了两个异构体，endo - 12和exo - 12，分别针对苄基碳上的取代基效应和环式π系统的受限制特征进行了讨论。 。化学选择性差异的起因与3-芳基化合物5的光芳基化产物6相比 还研究了光辐照产生的结果，并通过假定烯酮系统的β位置具有更高的反应性进行了合理化。
• A Breakthrough for the Photochemical Arylation in the 3-(Phenylmethyl)-2(5H)-furanone system Leading to the Tetrahydroindenofuranone System
  作者：Osamu Muraoka、Genzoh Tanabe、Kyoko Sano、Takefumi Momose

  DOI：10.3987/com-92-6034

  日期：——

  The photochemistry of the 'central methane'-substituted 3-benzyl-2(5H)-furanone system (1) is described. Despite its di-pi-methane structure, photochemical arylation was found to predominate in place of the di-pi-methane rearrangement, and gave substituted tetrahydroindenofuranones (2) in good yields.
• Accentuation of the Di-p-Methane Reactivity by Central Carbon Substitution in the 4-(Phenylmethyl)-2(5H)-furanone System
  作者：Osamu Muraoka、Genzoh Tanabe、Takefumi Momose

  DOI：10.3987/com-90-5502

  日期：——