5-ethyl 1-methyl 2-benzylidenepentanedioate | 128059-69-8

• 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: 5-ethyl 1-methyl 2-benzylidenepentanedioate
• 英文别名: 5-O-ethyl 1-O-methyl 2-benzylidenepentanedioate
• CAS: 128059-69-8；128059-70-1
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: ZBOYDSJNONQBGL-UHFFFAOYSA-N

物化性质

• 沸点：
  140-150 °C(Press: 1.60 Torr)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-(羟基苯基甲基)-丙烯酸甲酯 、 原乙酸三乙酯 在 sodium hydrogen sulfate 、 silica gel 作用下， 反应 1.0h， 以89%的产率得到5-ethyl 1-methyl 2-benzylidenepentanedioate
  参考文献：
  名称：

  Treatment of Baylis–Hillman adducts with triethyl orthoacetate in the presence of heterogeneous catalysts: a method for the stereoselective synthesis of two different types of trisubstituted alkenes

  摘要：

  Baylis-Hillman adducts on treatment with triethyl orthoacetate in the presence of HC104-SiO2 afford the corresponding allyl ethyl ethers while in the presence of NaHSO4SiO2 undergo the Johnson-Claisen rearrangement to form ethyl alk-4-enoates. Thus two different types of trisubstituted alkenes are produced in a stereoselective manner using two different hetereogeneous catalysts. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.060

文献信息

• Michael Addition of Methyl 2-(Trimethylsilyl)propenoate with Organomagnesiums or Organolithiums Leading to 1:1 and/or 2:1 Adducts and Subsequent Peterson Olefination by Condensation with Carbonyl Compounds
  作者：Junji Tanaka、Shuji Kanemasa、Yusuke Ninomiya、Otohiko Tsuge

  DOI：10.1246/bcsj.63.466

  日期：1990.2

  Michael addition of methyl 2-(trimethylsilyl)propenoate with organomagnesiums or organolithiums leads to 1:1 and/or 1:2 adduct anions which can be utilized in the subsequent step of Peterson olefination with carbonyl compounds. The 1:1/1:2 ratio depends upon the nature of donor molecules, the reaction conditions such as reaction temperature, polarity of solvent, and rate of addition of the acceptor

  2-(三甲基甲硅烷基)丙烯酸甲酯与有机镁或有机锂的迈克尔加成产生1:1和/或1:2的加合物阴离子，其可用于与羰基化合物的彼得森烯化的后续步骤。1:1/1:2 的比例取决于供体分子的性质、反应条件如反应温度、溶剂极性和受体分子的加入速率。过量使用受体会导致选择性形成 1:2 和/或 1:3 加合物。
• Treatment of Baylis–Hillman adducts with triethyl orthoacetate in the presence of heterogeneous catalysts: a method for the stereoselective synthesis of two different types of trisubstituted alkenes
  作者：Biswanath Das、Anjoy Majhi、Joydeep Banerjee

  DOI：10.1016/j.tetlet.2006.08.060

  日期：2006.10

  Baylis-Hillman adducts on treatment with triethyl orthoacetate in the presence of HC104-SiO2 afford the corresponding allyl ethyl ethers while in the presence of NaHSO4SiO2 undergo the Johnson-Claisen rearrangement to form ethyl alk-4-enoates. Thus two different types of trisubstituted alkenes are produced in a stereoselective manner using two different hetereogeneous catalysts. (c) 2006 Elsevier Ltd. All rights reserved.