(2RS,5SR)-trans-2,5-dimethyl-1-<1',3'-dioxo-2'-ethyl-3'-hydroxypropyl>pyrrolidine | 135469-55-5

• 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: (2RS,5SR)-trans-2,5-dimethyl-1-<1',3'-dioxo-2'-ethyl-3'-hydroxypropyl>pyrrolidine
• CAS: 135469-55-5；135469-56-6
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: BVEOXUSLINERQI-ZAZKALAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2RS,5SR)-trans-2,5-dimethyl-1-<1',3'-dioxo-2'-ethyl-3'-hydroxypropyl>pyrrolidine 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以84%的产率得到(2RS,5SR)-trans-2,5-dimethyl-1-<1',3'-dioxo-3'-chloro-2'-ethylpropyl>pyrrolidine
  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
• 作为产物：
  描述：

  (2RS,5RS)-trans-2,5-dimethyl-1-<1',3'-dioxo-2'-ethyl-3'-ethoxypropyl>pyrrolidine 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以97%的产率得到(2RS,5SR)-trans-2,5-dimethyl-1-<1',3'-dioxo-2'-ethyl-3'-hydroxypropyl>pyrrolidine
  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