3-phenyl-3-hydroxy-2-methylene-propanoic acid phenyl ester | 144261-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-phenyl-3-hydroxy-2-methylene-propanoic acid phenyl ester
• 英文别名: 2-[(hydroxy)(phenyl)methyl]-1-phenoxyprop-2-en-1-one；2-[hydroxy-(phenyl)methyl]acrylic acid phenyl ester；phenyl 2-[hydroxy(phenyl)methyl]acrylate；Phenyl 2-[hydroxy(phenyl)methyl]prop-2-enoate
• CAS: 144261-51-8
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: OGTJZBXJYPDZPB-UHFFFAOYSA-N

物化性质

• 沸点：
  437.9±34.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  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 phenyl ester 在 三乙烯二胺 作用下， 生成 丙烯酸苯酯
  参考文献：
  名称：

  Baylis-Hillman条件下丙烯酸芳基酯的反应

  摘要：

  据报道在Baylis-Hillman反应中使用丙烯酸芳基酯。与它们的烷基对应物相比，这些丙烯酸酯与醛的反应非常快，通常会由于起始加合物与醛的第二个分子的反应而产生环状产物。

  DOI：

  10.1016/0040-4039(96)00115-3
• 作为产物：
  描述：

  苯酚 在 三乙烯二胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 3-phenyl-3-hydroxy-2-methylene-propanoic acid phenyl ester
  参考文献：
  名称：

  Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates

  摘要：

  The catalytic direct alpha-alkylation of aldehydes with 2-(bromomethyl)acrylates has been accomplished, giving rise to alpha-branched and functionalized aldehydes of high diastereo- and enantiopurity. The influence of the nature of the ester group of the acrylates in reaction stereoselectivity and especially in reactivity is investigated. Optimum conditions implicate the use of phenyl acrylates in conjunction with organocatalyst 8. Application of thus obtained adducts in synthesis is illustrated with a concise stereocontrolled preparation of trisubstituted cyclopentenes.

  DOI：

  10.1021/jo202073n

文献信息

• Baylis-Hillman Reaction of Arylaldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate, and Phenyl Thioacrylate
  作者：Min Shi、Chao-Qun Li、Jian-Kang Jiang

  DOI：10.1002/1522-2675(200204)85:4<1051::aid-hlca1051>3.0.co;2-v

  日期：2002.4

  the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone, we found that the diadduct 4 was exclusively formed, and that the yield of 4 can reach 80% with increasing amounts of phenyl vinyl ketone. But, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The substituent effects were also examined, and a plausible reaction mechanism was proposed

  在芳基醛与苯基乙烯基酮的 Baylis-Hillman 反应中，我们发现双加合物 4 是完全形成的，并且随着苯基乙烯基酮用量的增加， 4 的收率可以达到 80%。但是，对于丙烯酸苯酯和硫代丙烯酸苯酯，只能得到正常的 Baylis-Hillman 加合物。还检查了取代基效应，并提出了形成 4 的合理反应机制。
• Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate
  作者：Min Shi、Chao-Qun Li、Jian-Kang Jiang

  DOI：10.3390/71000721

  日期：——

  In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausible reaction

  在芳基醛与苯基乙烯基酮的 Baylis-Hillman 反应中，我们观察到了双加合物 4 的独家形成，并且随着苯基乙烯基酮用量的增加，二加合物的产率可以达到 80%。另一方面，对于丙烯酸苯酯和硫代丙烯酸苯酯，只能得到正常的 Baylis-Hillman 加合物。还检查了取代基的影响，并提出了形成化合物 4 的合理反应机制。
• A remarkable rate acceleration of the Baylis–Hillman reaction
  作者：Wei-Der Lee、Kung-Shuo Yang、Kwunmin Chen

  DOI：10.1039/b103644k

  日期：——

  alpha-naphthyl acrylate with both aliphatic and aromatic aldehydes in the presence of DABCO (30 mol%) afforded the desired (alpha-methylene-beta-hydroxy)esters with reasonable chemical yields (51-88%) within 20 min.

  在 DABCO (30 mol%) 存在下用脂肪族和芳香族醛处理 α-丙烯酸萘酯在 20 分钟内以合理的化学产率 (51-88%) 提供所需的 (α-亚甲基-β-羟基) 酯。
• 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.
• Development of n-Type Semiconductor Based on Cyclopentene- or Cyclohexene-Fused [C₆₀]-Fullerene Derivatives
  作者：Yu Yamane、Kiyotaka Sugawara、Naoshi Nakamura、Shuichi Hayase、Toshiki Nokami、Toshiyuki Itoh

  DOI：10.1021/acs.joc.5b00530

  日期：2015.5.1

  Properties of cydopentene- or cyclohexene-fused [C-60]-fullerene derivatives as the acceptor in photovoltaic cells have been investigated by use of poly(3-hexylthiophene) (P3HT) as the model donor polymer. Several cyclopentene- or cyclohexene-fused [C-60]-fullerene derivatives show high power conversion efficiency (PCB). The highest PCE was obtained for 3',6'-dihydro-4'-phenoxycarbonyl-6'-methylbenzo[1,9][5,6] (C-60-I-h)fullerene (3.2%); this is superior to that of [C-60]-PCBM with the P3HT polymer under the same experimental conditions. PCE of the OPV devices with alkyl-substituted cydohexene-fused [C-60],fullerenes depended on the alkyl substituent on the cyclohexene ring; compounds with substituents of odd-number alkyl groups showed better PCE than those compounds possessing even-number alkyl groups.