(Z)-Methyl 3-phenyl-2-pentenoate | 84009-51-8

• 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: (Z)-Methyl 3-phenyl-2-pentenoate
• 英文别名: methyl (Z)-3-phenyl-2-pentenoate；3-phenyl-pent-2t-enoic acid methyl ester；3-Phenyl-pent-2t-ensaeure-methylester；methyl (2Z)-3-phenylpent-2-enoate；methyl (Z)-3-phenylpent-2-enoate
• CAS: 84009-51-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ROEVDKBMXAIMTK-KTKRTIGZSA-N

物化性质

• 沸点：
  274.8±10.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (Z)-Methyl 3-phenyl-2-pentenoate 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到2,3-Diethyl-5-oxo-2,3-diphenyl-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Nishiguchi, Ikuzo; Hirashima, Tsuneaki, Angewandte Chemie, 1983, vol. 95, # 1, p. 61 - 62

  摘要：

  DOI：
• 作为产物：
  描述：

  O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 、 苯丙酮 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90%的产率得到(Z)-Methyl 3-phenyl-2-pentenoate
  参考文献：
  名称：

  New reaction mode of the Horner–Wadsworth–Emmons reaction using Sn(OSO2CF3)2 and N-ethylpiperidine

  摘要：

  在甲基双(三氟乙基)膦酸酯2与芳基烷基酮3a～d或醛3f、g的Horner-Wadsworth-Emmons反应中，使用Sn(OSO2CF3)2并在N-乙基哌啶的存在下，观察到了优异的Z或E选择性，这与使用氢化钠的反应模式应有所不同。

  DOI：

  10.1039/a608495h

文献信息

• Formation of unsaturated esters in the single electron transfer reaction of cyclopropanone acetals with quinones under non-irradiated conditions
  作者：Manabu Abe、Akira Oku

  DOI：10.1016/s0040-4039(00)73235-7

  日期：1994.5

  Unsaturated esters were formed from cyclopropanone acetals in the reaction with DDQ or chloranil, where ring-opened CC and CO bonded adducts were the intermediates formed via a SET mechanism resulting in the ester formation.

  在与DDQ或邻苯二甲酰氯的反应中，环丙烷丙酮缩醛形成不饱和酯，其中开环的CC和C bondedO键合的加合物是通过SET机理形成的中间体，导致形成酯。
• (E)-Selective Horner–Wadsworth–Emmons reaction of aryl alkyl ketones with bis(2,2,2-trifluoroethyl)phosphonoacetic acid
  作者：Shigeki Sano、Yuka Takemoto、Yoshimitsu Nagao

  DOI：10.1016/j.tetlet.2003.09.185

  日期：2003.12

  The stereoselective Horner–Wadsworth–Emmons reaction of aryl alkyl ketones with bis(2,2,2-trifluoroethyl)phosphonoacetic acid utilizing lithium hexamethyldisilazide in DMF afforded (E)-α,β-unsaturated carboxylic acids as the major products.

  利用六甲基二硅叠氮化锂在DMF中进行的芳基烷基酮与双（2,2,2-三氟乙基）膦乙酸的立体选择性Horner-Wadsworth-Emmons反应得到（E）-α，β-不饱和羧酸作为主要产物。
• Stereoselective Synthesis of Tetrasubstituted (Z)-Alkenes from Aryl Alkyl Ketones Utilizing the Horner-Wadsworth-Emmons Reaction.
  作者：Shigeki Sano、Tomoka Takehisa、Shiho Ogawa、Kenji Yokoyama、Yoshimitsu Nagao

  DOI：10.1248/cpb.50.1300

  日期：——

  Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate with aryl alkyl ketones by employing Sn(OSO(2)CF(3))(2) and N-ethylpiperidine.

  通过使用Sn（OSO（2）CF（3），将2- [双（2,2,2-三氟乙基）膦酸]丙酸甲酯与芳基烷基酮通过Horner-Wadsworth-Emmons反应轻松制备四取代（Z）-烯烃））（2）和N-乙基哌啶。
• Process for the preparation of an ester of a 3-aryl-substituted acrylic acid
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0279474A1

  公开（公告）日：1988-08-24

  Process for the preparation of an ester of a 3-aryl-­substituted acrylic acid by reacting (a) a substituted aromatic hydrocarbon containing a 1-alkenyl group with one or two hydrogen atoms in beta-position, (b) CO and (c) an alcohol in the presence of a Group 8 noble metal or a compound thereof, a quinone and a redox agent.

  在第 8 族贵金属或其化合物、醌和氧化还原剂的存在下，使(a)含有 1-烯基并在β位有一个或两个氢原子的取代芳香烃、(b)CO 和(c)醇反应制备 3-芳基取代的丙烯酸酯的工艺。
• Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone
  作者：Akira Oku、Manabu Abe、Masaharu Iwamoto

  DOI：10.1021/jo00103a043

  日期：1994.12

  The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron accepters (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e. With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6. In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated. With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occurred. The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors. The mechanism of the reaction with quinones, in particular, was investigated in detail.