(2R,5R)-1-acryloyl-2,5-dimethylpyrrolidine | 129151-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,5R)-1-acryloyl-2,5-dimethylpyrrolidine
• 英文别名: 1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]prop-2-en-1-one
• CAS: 129151-19-5
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: GSMFRHZTGCWYBC-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2R,5R)-1-acryloyl-2,5-dimethylpyrrolidine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 正己烷 、 苯 为溶剂， 反应 9.5h， 生成 (2S,4R)-4-((2R,5R)-2,5-Dimethyl-pyrrolidine-1-carbonyl)-1,7-bis-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-2-ethyl-heptane-1,7-dione
  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

• Stereoselective radical reactions with chiral acrylamides and methacrylamides
  作者：Bernd Glese、Ursula Hoffmann、Martin Roth、Andreas Velt、Caroline Wyss、Margaretha Zehnder、Hendrik Zipse

  DOI：10.1016/s0040-4039(00)60437-9

  日期：1993.4

  Stereoselective radical reactions are observed with chiral methacrylamides 3 and 7. although the π-systems are twisted to a considerable extent.

  观察到手性甲基丙烯酰胺3和7的立体选择性自由基反应。尽管π系统在相当大的程度上扭曲了。
• 1,2- And 1,4-stereoinduction in reactions of chiral radicals
  作者：Bernd Giese、Margareta Zehnder、Martin Roth、Heinz Georg Zeitz

  DOI：10.1021/ja00174a061

  日期：1990.8
• Addition reactions of amide-substituted radicals: control of stereochemistry in acrylamide free-radical additions
  作者：Ned A. Porter、Elizabeth Swann、James Nally、Andrew T. McPhail

  DOI：10.1021/ja00174a060

  日期：1990.8
• PORTER, NED A.;SWANN, ELIZABETH;NALLY, JAMES;MCPHAIL, ANDREW T., J. AMER. CHEM. SOC., 112,(1990) N8, C. 6740-6741
  作者：PORTER, NED A.、SWANN, ELIZABETH、NALLY, JAMES、MCPHAIL, ANDREW T.

  DOI：——

  日期：——