(2R)-diethyl-2-ethyl-1,4-succinate | 58310-00-2

• 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: (2R)-diethyl-2-ethyl-1,4-succinate
• 英文别名: R-(+)-2-ethyldimethylsuccinate；(R)-2-Ethylbernsteinsaeuredimethylester；dimethyl (2R)-2-ethylbutanedioate
• CAS: 58310-00-2
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: RZZLQHQXWZLBCJ-ZCFIWIBFSA-N

物化性质

• 沸点：
  99 °C(Press: 14 Torr)
• 密度：
  1.041 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  6
• 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
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-diethyl-2-ethyl-1,4-succinate 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 吡啶 、 乙醚 、 乙醇 为溶剂， 反应 10.0h， 生成 R-(-)-N-benzyl-3-ethylpyrrolidine
  参考文献：
  名称：

  Bettoni, Giancarlo; Cellucci, Carla; Berardi, Francesco, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 603 - 605

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙基戊-4-烯酸 生成 (2R)-diethyl-2-ethyl-1,4-succinate
  参考文献：
  名称：

  Akermark,B., Acta Chemica Scandinavica (1947), 1962, vol. 16, p. 599 - 606

  摘要：

  DOI：

文献信息

• Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries
  作者：Jing Lin、Wing Hong Chan、Albert W.M. Lee、Wai Yeung Wong

  DOI：10.1016/s0040-4020(99)00872-8

  日期：1999.12

  The use of enantiomerically pure sultams (+)-1 and (−)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α-bromopropanoate or α-bromobutanoate

  完整描述了对映体纯的阿马酚（+）- 1和（-）- 1作为不对称烷基化反应的实际手性助剂。衍生自助剂的N-酰化产物用六甲基二硅叠氮化钠脱质子，然后用烷基卤化物处理，得到具有高非对映选择性的产物。用过量的外消旋α-溴丙酸酯或α-溴丁酸酯处理时，相应的N-酰基sultam的烯酸酯经历高度非对映选择性烷基化，以提供完全绝对控制两个连续手性中心的产物。
• Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Chiral Auxiliary:  Stereoselective Alkylation of α-Bromo Amides with Malonic Ester Enolates
  作者：Akira Kubo、Hitoshi Kubota、Masami Takahashi、Ken-ichi Nunami

  DOI：10.1021/jo970484q

  日期：1997.8.1

  Stereoselective carbon-carbon bond formation by dynamic kinetic resolution using tert-butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. Reaction of a diastereomeric mixture of tert-butyl (4S)-3-[(2RS)-2-bromoacyl]-1-methyl-2-oxoimidazolidine-4-carboxylates (2) with a malonic ester enolate in HMPA predominantly afforded tert-butyl (4S)-3-[(2R)-2-alkyl-3,3-bis(alkoxycarbonyl)propionyl]-1-methyl-2-oximidazolidine-4-carboxylate [(S,R)-8] in good yields. The stereoselectivity of this reaction was in accordance with our working hypothesis based on the conformational analysis of 2 and elucidated the unique characteristics of 1 as a novel chiral auxiliary for dynamic kinetic resolution. The alkylated products (S,R)-8ej,k were easily converted to chiral cx-alkyl succinic acid derivatives and chiral beta-amino acid derivatives, both of which have been known as key building blocks for the syntheses of a variety of biologically active compounds.
• BETTONI G.; CELLUCCI C.; BERARDI F., J. HETEROCYCL. CHEM., 1980, 17, NO 3, 603-605
  作者：BETTONI G.、 CELLUCCI C.、 BERARDI F.

  DOI：——

  日期：——