3-phenylprop-1-en-2-yl benzoate | 1197032-27-1

• 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: 3-phenylprop-1-en-2-yl benzoate
• 英文别名: 4-phenylprop-1-en-2-yl benzoate
• CAS: 1197032-27-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: PWNQAGHCEXUEAM-UHFFFAOYSA-N

物化性质

• 沸点：
  371.0±35.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylprop-1-en-2-yl benzoate 在 甲醇 、 C₃₈H₄₆O₃P₂*C₇H₈*Rh⁽¹⁺⁾*BF₄^(1-) 、 氢气 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、400.01 kPa 条件下， 反应 40.0h， 生成 (R)-1-苯基-2-丙醇
  参考文献：
  名称：

  1-烷基乙烯基苯甲酸酯的高度对映选择性加氢：手性2-烷基醇的简单，非酶促途径

  摘要：

  走向手性！描述了通过使用带有P bearingOP配体的Rh催化剂对烯醇酯1的高度对映选择性催化氢化（参见方案； NBD ＝降冰片二烯）。该催化体系具有广泛的范围，并允许制备具有高对映选择性的各种带有各种烷基或苄基的手性酯2。这些酯可以很容易地转化为高度对映体富集的2-链烷醇。

  DOI：

  10.1002/chem.201303500
• 作为产物：
  描述：

  4-苯基-1-丁炔 、 苯甲酸 在 六氟磷酸银 、 三苯基膦氯金 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以77%的产率得到3-phenylprop-1-en-2-yl benzoate
  参考文献：
  名称：

  Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes

  摘要：

  Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products via the Markonikov products

  DOI：

  10.1021/jo101543q

文献信息

• Trifluoromethanesulfonic Acid Catalyzed Isomerization of Kinetic Enol Derivatives to the Thermodynamically Favored Isomers
  作者：Phil Ho Lee、Dongjin Kang、Subin Choi、Sunggak Kim

  DOI：10.1021/ol2012132

  日期：2011.7.1

  Trifluoromethanesulfonic acid catalyzed isomerization of kinetic enol derivatives to the thermodynamically favored isomers was developed. Under the present conditions, kinetic enol phosphates, enol acetates and benzoates, and enol sulfonates were smoothly isomerized to produce the corresponding thermodynamically favored isomers in good to excellent yields.

  开发了三氟甲磺酸催化的动力学烯醇衍生物异构化为热力学上有利的异构体。在当前条件下，将动力学的烯醇式磷酸酯，烯醇式乙酸酯和苯甲酸酯和烯醇磺酸酯平滑地异构化，以良好至极好的收率生产相应的热力学上有利的异构体。
• Ruthenium(IV)-Catalyzed Markovnikov Addition of Carboxylic Acids to Terminal Alkynes in Aqueous Medium
  作者：Victorio Cadierno、Javier Francos、José Gimeno

  DOI：10.1021/om1010325

  日期：2011.2.28

  promote the selective Markovnikov addition of both aromatic and aliphatic carboxylic acids to a large variety of terminal alkynes, enynes, and diynes as well as propargylic alcohols. In this way, a wide number of enol esters and β-oxo esters could be synthesized in moderate to good yields under mild conditions (60 °C) in an aqueous medium.

  二聚的双（烯丙基）合钌（IV）配合物[的RuCl（μ-Cl）的（η 3：η 3 -C 10 ħ 16）} 2 ]（C 10 H ^ 16 = 2,7-二甲-2,6-二烯-1,8-二基）（5）和单核几个物种的反式-将[RuCl 2（η 3：η 3 -C 10 ħ 16）（L）]（L =二电子给体配体）（6）衍生的从5起已检查过使用水作为绿色反应介质将羧酸加成到末端炔烃上的催化剂。在活动和区域选择性方面的最佳结果与单核获得衍生物的反式-将[RuCl 2（η 3：η 3 -C 10 ħ 16）（PPH 3）]（6A），这是能够促进选择性Markovnikov加成芳族和脂族羧酸都可以用于各种末端炔烃，烯炔和二炔以及炔丙醇。以此方式，可以在温和条件下（60℃）在水性介质中以中等至良好的产率合成大量的烯醇酯和β-氧代酯。
• Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes
  作者：Jia-Feng Chen、Changkun Li

  DOI：10.1021/acs.orglett.8b02824

  日期：2018.11.2

  A cobalt-catalyzed highly regio- and stereoselective hydro-oxycarbonylation of alkynes is reported. Both terminal and internal alkynes can react with carboxylic acids to afford enol esters in high yields. The catalyst generated from Co(BF4)2, tridentate phosphine ligand L5, and zinc in situ exhibits much higher reactivity than the corresponding cobalt/diphosphine complex.

  据报道，炔烃具有钴催化的高度区域和立体选择性的氢氧羰基化作用。末端炔烃和内部炔烃均可与羧酸反应，以高收率得到烯醇酯。由Co（BF 4）2，三齿膦配体L5和原位锌生成的催化剂比相应的钴/二膦配合物具有更高的反应性。
• Asymmetric Hydrogenation of 1-Alkyl and 1-Aryl Vinyl Benzoates: A Broad Scope Procedure for the Highly Enantioselective Synthesis of 1-Substituted Ethyl Benzoates
  作者：Patryk Kleman、Pedro J. González-Liste、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/cs501402z

  日期：2014.12.5

  The enantioselective hydrogenation of enol esters of formula CH2=C(OBz)R with rhodium catalysts based on phosphine phosphite ligands (P-OP) has been studied. The reaction has a broad scope, and it is suitable for the preparation of products possessing a wide variety of R substituents. For the cases where R is a primary alkyl, high catalyst activity (S/C = 500) and enantioselectivities (95-99% ee) were obtained with a catalyst characterized by an ethane backbone and a PPh2 fragment. In contrast, for R = t-Bu, a catalyst possessing a benzene backbone provided the best results (97% ee). Derivatives with a cycloalkyl R substituent were particularly difficult substrates for this reaction. A broader catalyst screening was required for these substrates, which identified a catalyst possessing a P(m-xylyl)(2) fragment as the most appropriate one, affording enantioselectivities between 90 and 95% ee. Outstanding enantioselectivities (99% ee) and high catalyst activity (S/C = 500-1000) were also obtained in the case of substrates bearing a Ph or a fluoroaryl R substituent. In addition, the system is also appropriate for the preparation of other synthetically useful esters as those for R = benzyl, 2-phenylethyl or N-phthalimido alkyl chains. Likewise, the hydrogenation of divinyl dibenzoates proceeded with very high diastero- and enantioselectivity, generating rather low amounts of the meso isomer (3-6%). On the other hand, substrates with Br and MeO substituents at the phenyl benzoate ring, suitable for further functionalization, have also been examined. The results obtained indicate no detrimental effect of these substituents in the hydrogenation. Alternatively, the methodology has been applied to the highly enantioselective synthesis of deuterium isotopomers of 1-octyl benzoate bearing CDH2, CD2H, or CD3 fragments. Finally, as a practical advantage of the present system, it has been observed that the high performance of the catalysts is retained in highly concentrated solutions or even in the neat substrate, minimizing both the amount of solvent added and the volume of the reaction.
• Gold(I)-Catalyzed Addition of Carboxylic Acids to Alkynes
  作者：Bathoju Chandra Chary、Sunggak Kim

  DOI：10.1021/jo101543q

  日期：2010.11.19

  Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products via the Markonikov products