(±)-2,5-diethyl-2-phenyl-4-hexenoic acid | 120505-98-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (±)-2,5-diethyl-2-phenyl-4-hexenoic acid
• 英文别名: 2,5-Dimethyl-2-phenyl-4-hexenoic acid；2,5-dimethyl-2-phenylhex-4-enoic acid
• CAS: 120505-98-8
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: YIFORZCYSLIOCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-2,5-diethyl-2-phenyl-4-hexenoic acid 在 hydrochloride dihydrate salt 、 甲基锂 作用下， 生成 2-methyl-5-phenyl-2-hexene
  参考文献：
  名称：

  通过烷基锂诱导的不可烯化羧酸的脱羧作用来稳定化碳负离子。相当于hunsdiecker反应的阴离子

  摘要：

  在高度配位的溶剂中，甲基锂对α-苯基或α-苯硫基羧酸盐片段的亲核攻击而形成的中间二价阴离子，以生成稳定的碳负离子。一旦形成，这些阴离子可以方便地用各种亲电试剂官能化。

  DOI：

  10.1016/s0040-4039(00)80532-8

文献信息

• Kinetic Resolution of Racemic Carboxylic Acids through Asymmetric Protolactonization Promoted by Chiral Phosphonous Acid Diester
  作者：Masayuki Sakuma、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1021/ol401313d

  日期：2013.6.7

  salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S (= kfast/kslow) values. Asymmetric protolactonization also leads to the desymmetrization of achiral carboxylic acids. Notably, chiral phosphonous acid diester not only

  手性phospho盐通过不对称的原内酯化诱导外消旋α-取代的不饱和羧酸的动力学拆分。内酯和回收的羧酸均具有高对映选择性和高S（= k fast / k slow）值。不对称的原内酯化也导致非手性羧酸的去对称化。值得注意的是，手性亚膦酸二酯不仅诱导了对映选择性，而且还促进了原内酰胺化。
• Process for producing alpha-arylalkanoic acid esters
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0074008A2

  公开（公告）日：1983-03-16

  A process for producing an a-arylalkanoic acid ester represented by the general formula wherein Ar represents an aryl group which may optionally be substituted, and R' and R2, independently from each other, represents a lower alkyl group, which comprises reacting a Grignard reagent prepared from an aryl halide of the general formula wherein Ar is as defined above and X1 represents a halogen atom, and magnesium, with an a-haloalkanoic acid ester of the general formula wherein R' and R2 are as defined above, and X2 represents a halogen atom, said reaction of the Grignard reagent with the a-haloalkanoic acid ester of general formula (III) being carried out in the presence of a nickel compound.

  一种生产由通式表示的a-芳基烷酸酯的工艺，通式中Ar代表可选择被取代的芳基，而R'和R2彼此独立地代表低级烷基，该工艺包括将由通式中Ar如上所定义，X1代表卤素原子的芳基卤化物和镁制备的格氏试剂与通式中R'和R2如上所定义，X2代表卤素原子的a-卤代烷酸酯反应，所述格氏试剂与通式(III)的a-卤代烷酸酯的反应在镍化合物存在下进行。
• GILDAY, JOHN P.;RAQUETTE, LEO A., TETRAHEDRON LETT., 29,(1988) N 36, C. 4505-4508
  作者：GILDAY, JOHN P.、RAQUETTE, LEO A.

  DOI：——

  日期：——
• US4433160A
  申请人：——

  公开号：US4433160A

  公开（公告）日：1984-02-21
• Stabilized carbanions by alkyllithium-induced decarboxylation of non-enolizable carboxylic acids. An anionic equivalent to the hunsdiecker reaction
  作者：John P. Gilday、Leo A. Paquette

  DOI：10.1016/s0040-4039(00)80532-8

  日期：1988.1

  Intermediate dianions formed by nucleophilic attack of methyllithium on α-phenyl or α-phenylthio carboxylate salts fragment in highly coordinating solvents to produce stabilized carbanions. Once formed, these anions may be conveniently functionalized with various electrophilic reagents.

  在高度配位的溶剂中，甲基锂对α-苯基或α-苯硫基羧酸盐片段的亲核攻击而形成的中间二价阴离子，以生成稳定的碳负离子。一旦形成，这些阴离子可以方便地用各种亲电试剂官能化。