methyl 4-phenylpenta-2,3-dienoate | 57585-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-phenylpenta-2,3-dienoate
• 英文别名: 3-Phenyl-3-methyl-allencarbonsaeuremethylester；Methyl-4-phenylpenta-2,3-dienoat；Methyl 4-phenyl-2,3-pentadienoate
• CAS: 57585-09-8
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: ADOJEYYEFWCASS-UHFFFAOYSA-N

物化性质

• 沸点：
  311.5±12.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 4-phenylpenta-2,3-dienoate 在 palladium on barium sulfate 氢气 作用下， 生成 Methyl-4-phenylpent-3-enoat
  参考文献：
  名称：

  Crombie,L. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1090 - 1099

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基丙酰氯 生成 methyl 4-phenylpenta-2,3-dienoate
  参考文献：
  名称：

  Crombie,L. et al., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1090 - 1099

  摘要：

  DOI：

文献信息

• Tandem thia-Michael/Dieckmann condensation of allenyl esters for the regioselective synthesis of trisubstituted thiophenes
  作者：Michiyasu Nakao、Munehisa Toguchi、Yuki Shimabukuro、Shigeki Sano

  DOI：10.1016/j.tetlet.2020.152271

  日期：2020.9

  Tandem thia-Michael/Dieckmann condensation of allenyl esters with methyl mercaptoacetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded 2,3,5-trisubstituted thiophenes regioselectively. On the other hand, 2,3,4-trisubstituted thiophenes were obtained as the sole product by tandem thia-Michael/Dieckmann condensation employing magnesium bromide and triethylamine.

  在1,8-二氮杂双环[5.4.0]十一烷基-7-烯的存在下，烯丙基酯与巯基乙酸甲酯的串联硫杂-迈克尔/狄克曼缩合反应可选择性地提供2,3,5-三取代噻吩。另一方面，使用溴化镁和三乙胺，通过串联硫杂-迈克尔/狄克曼缩合反应，获得了2,3,4-三取代噻吩作为唯一产物。
• Synthesis of Novel 2,3-Disubstituted Thiophenes via Tandem Thia-Michael/Aldol Reaction of Allenyl Esters
  作者：Shigeki Sano、Michiyasu Nakao、Munehisa Toguchi、Ken Horikoshi、Syuji Kitaike

  DOI：10.3987/com-21-14575

  日期：——

  A tandem thia-Michael/aldol reaction of allenyl esters and mercaptoacetaldehyde in the presence of triethylamine provided 2,3,4-trisubstituted tetrahydrothiophenes. Novel 2,3-disubstituted thiophenes were obtained in high yield by the subsequent dehydration of the 2,3,4-trisubstituted tetrahydrothiophenes using p-toluenesulfonic acid monohydrate as an effective catalyst.

  在三乙胺存在下，烯丙酯和巯基乙醛的串联硫杂-迈克尔/羟醛反应提供了 2,3,4-三取代的四氢噻吩。使用对甲苯磺酸一水合物作为有效催化剂，通过随后对 2,3,4-三取代四氢噻吩进行脱水以高产率获得新型 2,3-二取代噻吩。
• Enantioselective preparation of allenecarboxylates by asymmetric horner-wadsworth-emmons reaction
  作者：Kiyoshi Tanaka、Kenji Otsubo、Kaoru Fuji

  DOI：10.1016/0040-4039(96)00672-7

  日期：1996.5

  Optically active 4,4-disubstituted conjugated allenecarboxylates were enantioselectively prepared via CC bond formation through an asymmetric Horner-Wadsworth-Emmons reaction with an optically active phosphonoacetate reagent.

  通过与光学活性膦酰基乙酸酯试剂的不对称Horner-Wadsworth-Emmons反应，通过CC键的形成，对映选择性地制备光学活性的4,4-二取代的共轭烯丙基羧酸酯。
• Synthesis of Allenyl Esters by Horner–Wadsworth–Emmons Reactions of Ketenes Mediated by Isopropylmagnesium Bromide
  作者：Shigeki Sano、Tomoya Matsumoto、Teppei Yano、Munehisa Toguchi、Michiyasu Nakao

  DOI：10.1055/s-0034-1378803

  日期：——

  The synthesis of conjugated allenyl esters (tri-substituted allenes) was achieved by magnesium(II)-mediated Horner-Wadsworth-Emmons reaction of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate with disubstituted ketenes. In addition, a novel access to -fluorinated allenyl carboxamides (tetrasubstituted allenes) is presented.
• Enantioselective synthesis of allenecarboxylates from phenyl acetates through CC bond forming reactions
  作者：Jiro Yamazaki、Toshiyuki Watanabe、Kiyoshi Tanaka

  DOI：10.1016/s0957-4166(01)00114-8

  日期：2001.3

  A variety of optically active 4,4-disubstituted allenecarboxylic acid methyl esters were prepared from simple alpha,alpha -disubstituted phenyl acetate through base treatment of the esters to generate ketenes, followed by successive Horner-Wadsworth-Emmons reaction. The transformation was further developed as a one-pot procedure with satisfactory yields and high enantioselectivity. (C) 2001 EIsevier Science Ltd. All rights reserved.