(+/-)-2-(E)-ethylidene-3-methyl-glutaric acid | 78217-22-8

• 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-(E)-ethylidene-3-methyl-glutaric acid
• 英文别名: (+/-)-2-(E)-Aethyliden-3-methyl-glutarsaeure；(2E)-2-ethylidene-3-methylpentanedioic acid
• CAS: 78217-22-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: YWWMXUSXCHIVFX-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethyl 4-methylpent-2-ene-3,5-dicarboxylate 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (+/-)-2-(E)-ethylidene-3-methyl-glutaric acid
  参考文献：
  名称：

  Catalytic Dimerization of Crotonates

  摘要：

  A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene ((IPr2Me2)-Pr-i) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.

  DOI：

  10.1021/acscatal.5b00930

文献信息

• Ethylenic acyl cyanides III : base induced self-condensation of ethylenic acyl cyanides.
  作者：Abdelkebir Jellal、Maurice Santelli

  DOI：10.1016/s0040-4039(00)88040-5

  日期：1983.1

  Tertiary amines promote formation of ethylenic acyl cyanide enolates which add with high chemo-selectivity on acyl cyanides giving unsaturated δ-lactones.

  叔胺促进烯属酰基氰化物烯醇化物的形成，其对酰基氰化物具有高化学选择性，从而产生不饱和的δ-内酯。
• Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the S_RN1 Mechanism
  作者：Jim-Wah Wong、Kenneth J. Natalie、Godson C. Nwokogu、Jyothi S. Pisipati、Patrick T. Flaherty、Thomas D. Greenwood、James F. Wolfe

  DOI：10.1021/jo962353f

  日期：1997.9.1

  Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the S(RN)1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).
• Base-catalyzed reactions of .alpha.,.beta.-unsaturated esters and nitriles. 4. Dimerization of .beta.-alkyl-substituted acrylates
  作者：Joseph Shabtai、Eva Ney-Igner、Herman Pines

  DOI：10.1021/jo00332a006

  日期：1981.9
• SHABTAI, J.;NEY-IGNER, E.;PINES, H., J. ORG. CHEM., 1981, 46, N 19, 3795-3802
  作者：SHABTAI, J.、NEY-IGNER, E.、PINES, H.

  DOI：——

  日期：——
• Catalytic Dimerization of Crotonates
  作者：James C. A. Flanagan、Eun Joo Kang、Nathaniel I. Strong、Robert M. Waymouth

  DOI：10.1021/acscatal.5b00930

  日期：2015.9.4

  A room-temperature dimerization of crotonates into 2-ethylidene-3-methylpentanedioates provides a sustainable route to difunctional monomers for step-growth polymerizations. We report two such dimerizations: (1) an organocatalytic dimerization using the N-heterocyclic carbene 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene ((IPr2Me2)-Pr-i) and (2) a rapid dimerization (under 15 s to full conversion) using potassium t-butoxide in THF. In addition to unsaturated diesters, the resulting dimers can be easily converted to other step-growth monomers; namely, their corresponding diacids and saturated diesters.