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

中文名称
——
中文别名
——
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
(2R,5R)-1-acryloyl-2,5-dimethylpyrrolidine化学式
CAS
129151-19-5
化学式
C9H15NO
mdl
——
分子量
153.224
InChiKey
GSMFRHZTGCWYBC-HTQZYQBOSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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偶氮二异丁腈三正丁基氢锡 作用下, 以 正己烷 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
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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:——
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同类化合物

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