ditert-butyl (2Z)-2-ethylidene-3-methylpentanedioate | 194096-96-3

• 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: ditert-butyl (2Z)-2-ethylidene-3-methylpentanedioate
• CAS: 194096-96-3
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: VDNHFADGKNYLTR-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  ditert-butyl (2Z)-2-ethylidene-3-methylpentanedioate 在 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以88%的产率得到(+/-)-2-(E)-ethylidene-3-methyl-glutaric acid
  参考文献：
  名称：

  Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the S_RN1 Mechanism

  摘要：

  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).

  DOI：

  10.1021/jo962353f
• 作为产物：
  描述：

  1-丁烯-4-酸叔丁酯 在 2-溴吡啶 、 potassium amide 作用下， 生成 (E)-4-Pyridin-2-yl-but-3-enoic acid tert-butyl ester 、 ditert-butyl (2Z)-2-ethylidene-3-methylpentanedioate
  参考文献：
  名称：

  Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the S_RN1 Mechanism

  摘要：

  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).

  DOI：

  10.1021/jo962353f

文献信息

• 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.
• 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：——