dimethyl 3-methyl-2-phenylpentanedioate | 112473-18-4

• 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: dimethyl 3-methyl-2-phenylpentanedioate
• CAS: 112473-18-4；112473-19-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: NMKRSEJBWRBTIK-UHFFFAOYSA-N

物化性质

• 沸点：
  327.6±30.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 3-methyl-2-phenylpentanedioate 在 lithium aluminium tetrahydride 作用下， 生成 3-methyl-2-phenylpentane-1,5-diol
  参考文献：
  名称：

  Stereochemical differences in the michael addition of phenylacetic acid esters and dialkyl amides to methyl cinnamate or methyl crotonate

  摘要：

  The stereochemistry of the conjugate addition of phenylacetic acid esters and dialkylamides to methyl crotonate is studied. The stereochemical results are compared with these previously obtained for the addition to methyl cinnamate. The differences observed are explained in terms of cyclic transition states with decreasing of the sterical interactions as a result of replacement of a phenyl group by methyl in position 2 of the 1,2-diphenylpropanic skeleton.

  DOI：

  10.1007/bf00818166
• 作为产物：
  描述：

  1,1,1-三甲氧基-2-丁烯 、 (1-methoxy-2-phenylvinyloxy)trimethylsilane 在 triphenylmethyl perchlorate 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到dimethyl 3-methyl-2-phenylpentanedioate
  参考文献：
  名称：

  α,β-Unsaturated Orthoesters as Michael Acceptors. The Trityl Salt-Catalyzed Michael Reaction of α,β-Unsaturated Orthoesters with Silyl Enol Ethers

  摘要：

  在一定量的三苯甲基盐催化下，α,β-不饱和邻位酯与各种硅基烯醇醚发生反应，生成相应的迈克尔加合物，收率很高。

  DOI：

  10.1246/cl.1987.1183

文献信息

• The Michael Reaction of O-Silylated Ketene Acetals with α,β-Unsaturated Esters Promoted by a Catalytic Amount of Aluminum Triflate
  作者：Nobuto Minowa、Teruaki Mukaiyama

  DOI：10.1246/cl.1987.1719

  日期：1987.9.5

  The Michael reaction of O-silylated ketene acetals with α,β-unsaturated ester in the presence of a catalytic amount of aluminum triflate proceeds smoothly under mild conditions to afford the corresponding glutarates in good yields.

  在催化量的三氟甲磺酸铝存在下，O-甲硅烷基化乙烯酮缩醛与α,β-不饱和酯的迈克尔反应在温和条件下顺利进行，以良好的产率得到相应的戊二酸酯。
• α-Ketophosphonates as Ester Surrogates: Isothiourea-Catalyzed Asymmetric Diester and Lactone Synthesis
  作者：Siobhan R. Smith、Stuart M. Leckie、Reuben Holmes、James Douglas、Charlene Fallan、Peter Shapland、David Pryde、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/ol500873s

  日期：2014.5.2

  Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using alpha-keto-beta,gamma-unsaturated phosphonates as alpha,beta-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or enantioenriched functionalized diesters upon ring-opening.
• Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Ping Lu、Jeffrey J. Jackson、John A. Eickhoff、Armen Zakarian

  DOI：10.1021/ja512213c

  日期：2015.1.21

  Michael addition is a premier synthetic method for carbon-carbon and carbon-heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.