methyl (Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enoate | 42443-26-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enoate
• 英文别名: methyl (Z)-2-(4-methoxyphenyl)-3-phenyl-acrylate；Methyl 2-(4-methoxyphenyl)-3-phenylacrylate
• CAS: 42443-26-5
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: UUZQFUIWMMQNPD-VBKFSLOCSA-N

物化性质

• 沸点：
  407.6±33.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯乙酸甲酯 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 水 、 triethylphosphonium tetrafluoroborate 、 四丁基碘化铵 、 lithium carbonate 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲苯 、 乙腈 为溶剂， 反应 36.0h， 生成 methyl (Z)-2-(4-methoxyphenyl)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Ru-Catalyzed C–H Arylation of Acrylic Acids with Aryl Bromides

  摘要：

  DOI：

  10.1021/acs.orglett.2c01043

文献信息

• Stereo- and Regioselective Palladium-Catalysed Hydroarylation and Hydrovinylation of Functionalised Alkynes: a Route to Substituted <i>Z</i>-2-Cinnamyl Esters, 3-Chromen-2-ols, and Coumarins
  作者：Sandro Cacchi、Giancarlo Fabrizi、Leonardo Moro、Paola Pace

  DOI：10.1055/s-1997-1040

  日期：——

  The palladium-catalysed hydroarylation and hydrovinylation of methyl 3-phenylpropynoate and 3,3-diethyoxy-1-(o-tetrahydropyranyloxy)phenyl-1-propyne with aryl and vinyl halides or triflates in the presence of Pd(OAc)2 and KOOCH has been studied. The reaction affords stereoselectively syn addition products. The regiochemical outcome appears to be controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon far from the aromatic ring ligated to the acetylenic carbon. The reaction can be applied to the synthesis of 3-substituted-3-chromen-2-ols and 3-substituted coumarins.

  钯催化的甲基3-苯基丙炔酸酯和3,3-二乙氧基-1-(o-四氢吡喃氧基)苯基-1-丙炔与芳基和乙烯基卤化物或三氟甲磺酸盐在Pd(OAc)2和KOOCH存在下的氢芳基化和氢乙烯基化反应已被研究。反应选择性地得到顺式加成产物。区域化学结果似乎受空间效应控制，新的碳-碳键优先在远离与炔碳连接的芳环的碳上生成。该反应可应用于3-取代的3-色满-2-醇和3-取代的香豆素的合成。
• General, Robust, and Stereocomplementary Preparation of α,β-Disubstituted α,β-Unsaturated Esters
  作者：Hidefumi Nakatsuji、Hiroshi Nishikado、Kanako Ueno、Yoo Tanabe

  DOI：10.1021/ol9013359

  日期：2009.10.1

  for α,β-disubstituted α,β-unsaturated esters is performed via three general and robust reaction sequences: (i) Ti−Claisen condensation (formylation) of esters to give α-formyl esters (12 examples, 60−99%), (ii) (E)- and (Z)-stereocomplementary enol p-toluenesulfonylation (tosylation) using TsCl−N-methylimidazole (NMI)−Et3N and LiOH (24 examples, 82−99%), and (iii) stereoretentive Suzuki−Miyaura cross-coupling

  α，β-二取代的α，β-不饱和酯的（E）-和（Z）-立体互补制备方法是通过三个常规且稳健的反应顺序进行的：（i）酯的Ti-Claisen缩合（甲酰化）得到α -甲酰基酯（12个例子，60-99％），（ii）（E）-和（Z）-立体互补烯醇对甲苯磺酰化（甲苯磺酸化），使用TsCl- N-甲基咪唑（NMI）-Et 3 N和LiOH（24实例82-99％）和（iii）立体保持Suzuki-Miyaura交叉耦合（18实例64-96％）。
• A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles
  作者：Daniel J. Kerr、Jonathan M. White、Bernard L. Flynn

  DOI：10.1021/jo100736p

  日期：2010.11.5

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
• Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381
  作者：Kerr, Daniel J.、Metje, Christiane、Flynn, Bernard L.

  DOI：——

  日期：——
• Garay, Raul O.; Cadaleiro, Mercedes C., Journal of Chemical Research, Miniprint, 1988, # 12, p. 2962 - 2971
  作者：Garay, Raul O.、Cadaleiro, Mercedes C.

  DOI：——

  日期：——