dimethyl 2-(4-oxo-4-phenylbutan-2-yl)malonate | 135741-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2-(4-oxo-4-phenylbutan-2-yl)malonate
• 英文别名: Dimethyl 2-(4-oxo-4-phenylbutan-2-yl)propanedioate
• CAS: 135741-11-6
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: NIAJWNYNWGSBOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苯基环丁烷-1-醇 、 丙二酸二甲酯 在 tetrabutylammonium tetrafluoroborate 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以42%的产率得到dimethyl 2-(4-oxo-4-phenylbutan-2-yl)malonate
  参考文献：
  名称：

  环烷醇开环电化学合成β-功能化酮

  摘要：

  已经研究了环烷醇与亲核试剂的电化学解构官能化，这使得官能化只发生在酮的β-位。底物范围包括范围广泛的环烷醇以及各种以 N、O、C 和 P 为中心的亲核试剂，可方便地使用 β-官能化酮作为产品。机理研究支持生成 α,β-不饱和酮作为关键中间体，然后与亲核试剂进行迈克尔加成。

  DOI：

  10.1021/acs.orglett.2c01649

文献信息

• Palladium(II)-assisted dialkylation and alkylation/acylation of optically active ene carbamates via trialkylorganostannane cross-coupling and carbonylative coupling processes
  作者：John J. Masters、Louis S. Hegedus、Joaquin Tamariz

  DOI：10.1021/jo00019a038

  日期：1991.9

  Alkylation of benzyl vinyl carbamate and propene with the anions of diethyl methylmalonate or dimethyl malonate in the presence of palladium (II) chloride, followed by cross-coupling or carbonylative cross-coupling with organostannanes, effected an overall dialkylation or alkylation/acylation of the monoolefin substrate. Complete control of stereochemistry in this palladium(II)-assisted reaction was observed using optically active ene carbamates affording beta-amino-unsaturated keto esters in good chemical yields and excellent optical purity.
• CaCl₂, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction
  作者：Kristin Lippur、Sandra Kaabel、Ivar Järving、Kari Rissanen、Tõnis Kanger

  DOI：10.1021/acs.joc.5b00769

  日期：2015.6.19

  A mild protocol for the asymmetric Michael addition of dimethyl malonate to various alpha,beta-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.
• Electrochemical Synthesis of β-Functionalized Ketones via Ring-Opening of Cycloalkanols
  作者：Lulu Zhao、Qiwen Zhong、Jian Tian、Mengqi Luo、Chao Yang、Lin Guo、Wujiong Xia

  DOI：10.1021/acs.orglett.2c01649

  日期：2022.6.24

  which allows functionalization to occur exclusively at the β-position of ketones. The substrate scope includes a wide range of cycloalkanols as well as diverse N, O, C, and P-centered nucleophiles, providing ready access to β-functionalized ketones as products. Mechanistic studies support the generation of α,β-unsaturated ketones as key intermediates followed by Michael addition with nucleophiles.

  已经研究了环烷醇与亲核试剂的电化学解构官能化，这使得官能化只发生在酮的β-位。底物范围包括范围广泛的环烷醇以及各种以 N、O、C 和 P 为中心的亲核试剂，可方便地使用 β-官能化酮作为产品。机理研究支持生成 α,β-不饱和酮作为关键中间体，然后与亲核试剂进行迈克尔加成。