2-(5-azidopent-1-ylidene)-1,3-dithiane | 144630-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-(5-azidopent-1-ylidene)-1,3-dithiane
• 英文别名: 2-(5-azidopentylidene)-1,3-dithiane
• CAS: 144630-02-4
• 化学式: C₉H₁₅N₃S₂
• 分子量: 229.37
• InChiKey: LXSAAVCKASMECS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(5-azidopent-1-ylidene)-1,3-dithiane 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 12.08h， 生成 2-哌啶甲醛,1-[(4-甲基苯基)磺酰]-
  参考文献：
  名称：

  Ketene-S,S-acetals as 1,3-dipolarophiles towards azides. A new synthetic entry into cyclic amino acids

  摘要：

  Intramolecular azide cycloaddition reactions of ketene-S,S-acetals proceed to give a reactive imine as the initially-formed intermediate and this mechanism is supported by thermolysis of (18) which gave the stable imine (22). N-Acylation of this intermediate leads to cyclic variants of 2-amino ketene-S,S-acetals (20, 24, 27), which can be viewed as masked alpha-amino acids, and reduction leads to the corresponding dithiane (21, 25, 29a). Both systems have been converted to cyclic alpha-amino acids and the scope, in terms of the ring sizes available, and the limitations of this intramolecular cycloaddition process are discussed.

  DOI：

  10.1016/s0040-4020(01)90368-0
• 作为产物：
  描述：

  bis-(dimethylaluminium)-1,3-propenedithiolate 、 6-叠氮基己酸甲酯 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 以67%的产率得到2-(5-azidopent-1-ylidene)-1,3-dithiane
  参考文献：
  名称：

  Ketene-S,S-acetals as 1,3-dipolarophiles towards azides. A new synthetic entry into cyclic amino acids

  摘要：

  Intramolecular azide cycloaddition reactions of ketene-S,S-acetals proceed to give a reactive imine as the initially-formed intermediate and this mechanism is supported by thermolysis of (18) which gave the stable imine (22). N-Acylation of this intermediate leads to cyclic variants of 2-amino ketene-S,S-acetals (20, 24, 27), which can be viewed as masked alpha-amino acids, and reduction leads to the corresponding dithiane (21, 25, 29a). Both systems have been converted to cyclic alpha-amino acids and the scope, in terms of the ring sizes available, and the limitations of this intramolecular cycloaddition process are discussed.

  DOI：

  10.1016/s0040-4020(01)90368-0

文献信息

• Ketene-S,S-acetals as 1,3-dipolarophiles towards azides. A new synthetic entry into cyclic amino acids
  作者：William O. Moss、Emma Wakefield、Mary F. Mahon、Kieran C. Molloy、Robert H. Bradbury、Neil J. Hales、Timothy Gallagher

  DOI：10.1016/s0040-4020(01)90368-0

  日期：1992.9

  Intramolecular azide cycloaddition reactions of ketene-S,S-acetals proceed to give a reactive imine as the initially-formed intermediate and this mechanism is supported by thermolysis of (18) which gave the stable imine (22). N-Acylation of this intermediate leads to cyclic variants of 2-amino ketene-S,S-acetals (20, 24, 27), which can be viewed as masked alpha-amino acids, and reduction leads to the corresponding dithiane (21, 25, 29a). Both systems have been converted to cyclic alpha-amino acids and the scope, in terms of the ring sizes available, and the limitations of this intramolecular cycloaddition process are discussed.