3-phenyl-3-hydroxy-2-methylene-propanoic acid allyl ester | 144261-77-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 3-phenyl-3-hydroxy-2-methylene-propanoic acid allyl ester
• 英文别名: Prop-2-enyl 2-[hydroxy(phenyl)methyl]prop-2-enoate
• CAS: 144261-77-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: PDZZTDOETXZDPN-UHFFFAOYSA-N

物化性质

• 沸点：
  347.5±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-hydroxy-2-methylene-propanoic acid allyl ester 在 Ru[(PCy₃)(=CHPh)(N,N'-Me₂-imidazolidin-2-yl)]Cl₂ 作用下， 以 甲苯 为溶剂， 反应 110.0h， 以11%的产率得到[(E)-4-[2-[hydroxy(phenyl)methyl]prop-2-enoyloxy]but-2-enyl] 2-[hydroxy(phenyl)methyl]prop-2-enoate
  参考文献：
  名称：

  Experimental and Theoretical Study on the Olefin Metathesis of Alkenyl Baylis−Hillman Adducts Using Second-Generation Grubbs Catalyst

  摘要：

  We have investigated the olefin metathesis from alkenyl Baylis-Hillman adducts using second-generation Grubbs catalyst. In the experiment, the ring-closing metathesis (RCM) product could not be found, while the cross-metathesis (CM) products were found. The computational studies provided consistent explanations for the experimental result. The most limiting factor for the RCM process using second-generation Grubbs catalyst is caused by the high strain and steric effect in the metallacyclobutane intermediates.

  DOI：

  10.1021/ol048776i
• 作为产物：
  描述：

  2-(羟基苯基甲基)-丙烯酸甲酯 在 氢氧化钾 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 3-phenyl-3-hydroxy-2-methylene-propanoic acid allyl ester
  参考文献：
  名称：

  Experimental and Theoretical Study on the Olefin Metathesis of Alkenyl Baylis−Hillman Adducts Using Second-Generation Grubbs Catalyst

  摘要：

  We have investigated the olefin metathesis from alkenyl Baylis-Hillman adducts using second-generation Grubbs catalyst. In the experiment, the ring-closing metathesis (RCM) product could not be found, while the cross-metathesis (CM) products were found. The computational studies provided consistent explanations for the experimental result. The most limiting factor for the RCM process using second-generation Grubbs catalyst is caused by the high strain and steric effect in the metallacyclobutane intermediates.

  DOI：

  10.1021/ol048776i

文献信息

• The ‘Baylis - Hillman Reaction’ mechanism and applications revisited
  作者：Yves Fort、Marie Christine Berthe、Paul Caubere

  DOI：10.1016/s0040-4020(01)88227-2

  日期：1992.1

  It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.
• Experimental and Theoretical Study on the Olefin Metathesis of Alkenyl Baylis−Hillman Adducts Using Second-Generation Grubbs Catalyst
  作者：Mi Jung Lee、Ka Young Lee、Jin Yong Lee、Jae Nyoung Kim

  DOI：10.1021/ol048776i

  日期：2004.9.1

  We have investigated the olefin metathesis from alkenyl Baylis-Hillman adducts using second-generation Grubbs catalyst. In the experiment, the ring-closing metathesis (RCM) product could not be found, while the cross-metathesis (CM) products were found. The computational studies provided consistent explanations for the experimental result. The most limiting factor for the RCM process using second-generation Grubbs catalyst is caused by the high strain and steric effect in the metallacyclobutane intermediates.