1-but-3-enylpyrrolidine-2-carbaldehyde | 135192-15-3

• 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: 1-but-3-enylpyrrolidine-2-carbaldehyde
• CAS: 135192-15-3
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: DJQFPPRAYVOEMV-UHFFFAOYSA-N

物化性质

• 沸点：
  243.9±23.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 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：
  2.0

反应信息

• 作为反应物：
  描述：

  1-but-3-enylpyrrolidine-2-carbaldehyde 在 正丁基锂 、 水 、 六甲基二硅氮烷 作用下， 反应 11.0h， 生成 2-(phenylimino)-1,2,3,4,4a,5,6,10b-octahydroindolizino<8,7-d><1,3>thiazine
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of 1-thia-3-azabutadienes. One-pot synthesis of annulated thiazines from N-(trimethylsilyl)imines and isothiocyanates

  摘要：

  The intramolecular [4 + 2] cycloaddition of 1-thia-3-aza dienes is described. Substituted N-(trimethylsilyl)imines 2 derived from aromatic and heteroaromatic aldehydes 1 react with isothiocyanates to form heterodienes 3, which, although not isolated, undergo intramolecular cycloaddition at 90-degrees-C to yield heteropolycyclic compounds 5 and 7. The process was found to be regioselective and stereospecific; the stereochemistry of the cycloadducts arises from an exo transition state.

  DOI：

  10.1021/jo00019a040
• 作为产物：
  描述：

  methyl N-(3-butenyl)-2-pyrrolidinecarboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.0h， 生成 1-but-3-enylpyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations

  摘要：

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.

  DOI：

  10.1021/jo00008a038

文献信息

• HASSNER, ALFRED;MAURYA, RAKESH;PADWA, ALBERT;BULLOCK, WILLIAM H., J. ORG. CHEM., 56,(1991) N, C. 2775-2781
  作者：HASSNER, ALFRED、MAURYA, RAKESH、PADWA, ALBERT、BULLOCK, WILLIAM H.

  DOI：——

  日期：——
• Cycloadditions. 46. Thermally induced intramolecular oxime olefin cycloadditions leading to N-bridgehead systems. Stereochemistry and molecular mechanics calculations
  作者：Alfred Hassner、Rakesh Maurya、Albert Padwa、William H. Bullock

  DOI：10.1021/jo00008a038

  日期：1991.4

  The intramolecular oxime olefin cycloaddition (IOOC) of proline and pipecolinic acid derivatives proceeds thermally with a high degree of stereoselectivity to provide a new route to functionalized pyrrolizidines, indolizidines, or quinolizidines. The ring closure proceeds with simultaneous stereoselective introduction of three or four stereocenters. Molecular mechanics calculations have been refined to accurately predict not only which stereoisomer is preferred but also the syn and anti coupling constants in these tricyclic molecules.
• Intramolecular Diels-Alder reactions of 1-thia-3-azabutadienes. One-pot synthesis of annulated thiazines from N-(trimethylsilyl)imines and isothiocyanates
  作者：Jose Barluenga、Miguel Tomas、Alfredo Ballesteros、Luis A. Lopez

  DOI：10.1021/jo00019a040

  日期：1991.9

  The intramolecular [4 + 2] cycloaddition of 1-thia-3-aza dienes is described. Substituted N-(trimethylsilyl)imines 2 derived from aromatic and heteroaromatic aldehydes 1 react with isothiocyanates to form heterodienes 3, which, although not isolated, undergo intramolecular cycloaddition at 90-degrees-C to yield heteropolycyclic compounds 5 and 7. The process was found to be regioselective and stereospecific; the stereochemistry of the cycloadducts arises from an exo transition state.