methyl 4-(3-(4-methoxyphenyl)-3-oxopropyl)benzoate | 1334709-36-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: methyl 4-(3-(4-methoxyphenyl)-3-oxopropyl)benzoate
• 英文别名: 4-[3-(4-methoxyphenyl)-3-oxo-propyl]benzoic acid methyl ester；Methyl 4-[3-(4-methoxyphenyl)-3-oxopropyl]benzoate；methyl 4-[3-(4-methoxyphenyl)-3-oxopropyl]benzoate
• CAS: 1334709-36-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: BDHTUDRHWHLYQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对溴苯甲酸甲酯 在 四氢吡咯 、 N-甲基二环己基胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二叔丁基膦-1-苯基吲哚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 methyl 4-(3-(4-methoxyphenyl)-3-oxopropyl)benzoate
  参考文献：
  名称：

  Double Arylation of Allyl Alcohol via a One-Pot Heck Arylation–Isomerization–Acylation Cascade

  摘要：

  A one-pot, two-step catalytic protocol has been developed. A regloselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.

  DOI：

  10.1021/ol202144z

文献信息

• Methanol as hydrogen source: Chemoselective transfer hydrogenation of α,β-unsaturated ketones with a rhodacycle
  作者：Ahmed H. Aboo、Robina Begum、Liangliang Zhao、Zahoor H. Farooqi、Jianliang Xiao

  DOI：10.1016/s1872-2067(19)63367-x

  日期：2019.11

  economic and easy-to-handle hydrogen source. It has rarely been used in transfer hydrogenation reactions, however. We herein report that a cyclometalated rhodium complex, rhodacycle, catalyzes highly chemoselective hydrogenation of α,β-unsaturated ketones with methanol as the hydrogen source. A wide variety of chalcones, styryl methyl ketones and vinyl methyl ketones, including sterically demanding

  摘要 甲醇是一种安全、经济且易于处理的氢源。然而，它很少用于转移氢化反应。我们在此报告了一种环金属化铑配合物，铑环，以甲醇为氢源催化 α,β-不饱和酮的高度化学选择性氢化。多种查耳酮、苯乙烯基甲基酮和乙烯基甲基酮，包括空间要求高的那些，在回流的甲醇中在很短的反应时间内被还原为饱和酮，不需要中间气体保护，也没有羰基部分的还原观察到的。所描述的催化提供了一种实际上简单且操作安全的方法，用于还原 α,β-不饱和酮化合物中的烯键。
• Utility of Organoboron Reagents in Arylation of Cyclopropanols via Chelated Pd(II) Catalysis: Chemoselective Access to β-Aryl Ketones
  作者：Thangeswaran Ramar、Murugaiah A. M. Subbaiah、Andivelu Ilangovan

  DOI：10.1021/acs.joc.0c00160

  日期：2020.6.19

  Organoborane reagents were investigated as coupling partners to cyclopropanol-derived β-ketone enolates in the presence of a chelated Pd(II) catalyst. Efficient coupling of a range of electronically and sterically diverse cyclopropanols and aryl/alkenyl boronic derivatives (39 examples, 65–94% yield) could be achieved with the generation of synthetically important β-aryl ketone intermediates in a chemoselective

  在螯合的Pd（II）催化剂存在下，研究了有机硼烷试剂作为与环丙醇衍生的β-酮烯酸酯的偶联伙伴。通过化学选择性的方式生成具有重要合成意义的重要的β-芳基酮中间体，可以实现多种电子和空间上不同的环丙醇与芳基/烯基硼酸酯衍生物的高效偶联（39个实例，收率65-94％）。这种反应范式将芳基供体伙伴的范围扩大至均烯酸酯，允许开瓶条件，以水为助溶剂并制备与以往方法不同的含卤素β-芳基酮。这种螯合的Pd（II）催化作用似乎不同于Pd（0）途径，
• Solid-Supported Cross-Metathesis and a Formal Alkane Metathesis for the Generation of Biologically Relevant Molecules
  作者：Luciana Méndez、Ernesto G. Mata

  DOI：10.1021/co500176b

  日期：2015.2.9

  Solid-phase synthetic strategies toward the generation of libraries of biologically relevant molecules were developed using olefin cross-metathesis as a key step. It is remarkably the formal alkane metathesis based on a one-pot, microwave-assisted, ruthenium-catalyzed cross-metathesis and reduction to obtain Csp3-Csp3 linkages.
• Double Arylation of Allyl Alcohol via a One-Pot Heck Arylation–Isomerization–Acylation Cascade
  作者：Paul Colbon、Jiwu Ruan、Mark Purdie、Keith Mulholland、Jianliang Xiao

  DOI：10.1021/ol202144z

  日期：2011.10.21

  A one-pot, two-step catalytic protocol has been developed. A regloselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.