2-(1-methyl-6-(N-methylamino)hex-3(Z)-enyl)-1,3-dioxolane | 145126-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(1-methyl-6-(N-methylamino)hex-3(Z)-enyl)-1,3-dioxolane
• 英文别名: (Z)-6-(1,3-dioxolan-2-yl)-N-methylhept-3-en-1-amine
• CAS: 145126-63-2
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: POJUKVTYPKMRKK-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-6-(N-methylamino)hex-3(Z)-enyl)-1,3-dioxolane 在 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 25.0~350.0 ℃ 、2.67 Pa 条件下， 反应 0.5h， 生成 4-butyl-3-(ethoxycarbonyl)-1-methyl-6-(2'-(1'',3''-dioxolanyl)propyl)-1,4-diazabicyclo<4.3.0>nonan-2-one
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

  摘要：

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.

  DOI：

  10.1021/jo00052a015
• 作为产物：
  描述：

  2-[(E)-5-phenylpent-4-en-2-yl]-1,3-dioxolane 在 四氧化锇 吡啶 、 lead(IV) acetate 、 sodium hexamethyldisilazane 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 5.33h， 生成 2-(1-methyl-6-(N-methylamino)hex-3(Z)-enyl)-1,3-dioxolane
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles

  摘要：

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.

  DOI：

  10.1021/jo00052a015

文献信息

• Henke Brad R., Kouklis Andrew J., Heathcock Clayton H., J. Org. Chem., 57 (1992) N 26, S 7056-7066
  作者：Henke Brad R., Kouklis Andrew J., Heathcock Clayton H.

  DOI：——

  日期：——
• Intramolecular 1,3-dipolar cycloaddition of stabilized azomethine ylides to unactivated dipolarophiles
  作者：Brad R. Henke、Andrew J. Kouklis、Clayton H. Heathcock

  DOI：10.1021/jo00052a015

  日期：1992.12

  The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of doubly-stabilized azomethine ylides to unactivated olefinic, acetylenic, and aromatic dipolarophiles is reported. The azomethine ylides studied were generated by flash vacuum pyrolysis of their corresponding aziridines and were found to add stereospecifically in good to excellent yields to a variety of unactivated dipolarophiles. Generation of the diazabicyclo[3.3.0]octane (e.g., 15a,b), diazabicyclo[4.3.0]nonane (e.g., 4,13), and diazabicyclo[5.3.0]decane (e.g., 15c) ring systems are possible using this technology. In addition, the first examples of cycloaddition of a stabilized azomethine ylide to benzene dipolarophiles are reported. Cycloadditions of this type generate highly functionalized triciclic systems with complete relative stereocontrol at the newly formed stereocenters (e.g., 24-26). Finally, it has been shown that cycloadducts 31 and 32 are in equilibrium, presumably by way of the intermediate azomethine ylide 33, under conditions of flash vacuum pyrolysis.