(+)-(S)-2-ethylglutaric acid | 70395-94-7

• 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: (+)-(S)-2-ethylglutaric acid
• 英文别名: d-I+/--AthylglutarsA currencyure；(2S)-2-ethylpentanedioic acid
• CAS: 70395-94-7
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: QHNBKRVBKPWUKG-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  diethyl 2-ethyl-2-(ethoxycarbonyl)glutarate 在 盐酸 作用下， 反应 20.0h， 生成 (+)-(S)-2-ethylglutaric acid
  参考文献：
  名称：

  Free-radical telomerization of chiral acrylamides: control of stereochemistry in additions and halogen-atom transfer

  摘要：

  The free-radical reactions of carbon radicals substituted alpha to a chiral pyrrolidine amide have been studied. The pyrrolidine used was 2,5-dimethylpyrrolidine, available as either the R,R or S,S enantiomer from D- or L-alanine, and the radicals were generated (1) by tin radical abstraction of the halogen from the 2-iodobutyramide of the pyrrolidine, (2) by decomposition of a pyrrolidine amide substituted Barton ester 4, and (3) by radical addition to the acrylamide of the pyrrolidine 3. Addition of chiral-alpha amide radicals to alkenes occurs with a selectivity of approximately 15:1 at room temperature, while bromine- and iodine-atom transfer to these radicals occurs with a selectivity of 10:1 at room temperature. Telomerization of the acrylamide 3 is achieved by photolysis of BrCCl3 in the presence of acrylamide. Telomers are readily formed and the lower telomers, n = 1 to 5, were isolated and characterized. Halogens were removed from the telomers by reduction with tributyltin hydride and in this way, the major diastereomers of the n = 2 and n = 3 telomers were converted to known compounds. Chain-transfer constants for the BrCCl3 telomerization were determined and they range from 0.3 to 0.5 for C(n) = C2 to C5. An analysis of the chiral amide auxiliary is presented that may prove useful in the consideration of other auxiliary groups.

  DOI：

  10.1021/ja00018a044

文献信息

• Free-radical telomerization of chiral acrylamides: control of stereochemistry in additions and halogen-atom transfer
  作者：Ned A. Porter、Robert Breyer、Elizabeth Swann、James Nally、Jyotsna Pradhan、Timothy Allen、Andrew T. McPhail

  DOI：10.1021/ja00018a044

  日期：1991.8

  The free-radical reactions of carbon radicals substituted alpha to a chiral pyrrolidine amide have been studied. The pyrrolidine used was 2,5-dimethylpyrrolidine, available as either the R,R or S,S enantiomer from D- or L-alanine, and the radicals were generated (1) by tin radical abstraction of the halogen from the 2-iodobutyramide of the pyrrolidine, (2) by decomposition of a pyrrolidine amide substituted Barton ester 4, and (3) by radical addition to the acrylamide of the pyrrolidine 3. Addition of chiral-alpha amide radicals to alkenes occurs with a selectivity of approximately 15:1 at room temperature, while bromine- and iodine-atom transfer to these radicals occurs with a selectivity of 10:1 at room temperature. Telomerization of the acrylamide 3 is achieved by photolysis of BrCCl3 in the presence of acrylamide. Telomers are readily formed and the lower telomers, n = 1 to 5, were isolated and characterized. Halogens were removed from the telomers by reduction with tributyltin hydride and in this way, the major diastereomers of the n = 2 and n = 3 telomers were converted to known compounds. Chain-transfer constants for the BrCCl3 telomerization were determined and they range from 0.3 to 0.5 for C(n) = C2 to C5. An analysis of the chiral amide auxiliary is presented that may prove useful in the consideration of other auxiliary groups.