2-(pyrrolidin-2-yl)-1,3-dithiane | 144630-04-6

• 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-(pyrrolidin-2-yl)-1,3-dithiane
• 英文别名: 2-(1,3-dithian-2-yl)pyrrolidine
• CAS: 144630-04-6
• 化学式: C₈H₁₅NS₂
• 分子量: 189.346
• InChiKey: GHXWKSXBAVVEDD-UHFFFAOYSA-N

物化性质

• 沸点：
  308.4±32.0 °C(predicted)
• 密度：
  1.155±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴戊酸甲酯 在 potassium iodide sodium tetrahydroborate 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 95.0h， 生成 2-(pyrrolidin-2-yl)-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 dithioacetals as 1,3-dipolarophiles. Applications to the synthesis of cyclic amino acids
  作者：William O. Moss、Robert H. Bradbury、Neil J. Hales、Timothy Gallagher

  DOI：10.1039/c39900000051

  日期：——

  Intramolecular azide cycloaddition reactions of ketene dithioacetals provide a new route to cyclic amino acids and a stereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyproline (14) based on this methodology is described.

  烯酮二硫缩醛的分子内叠氮化物环加成反应提供了通往环状氨基酸的新途径，并描述了基于该方法的立体选择性合成（2 S，3 S，4 R）-3,4-二羟基脯氨酸（14）。
• Intramolecular Hydroamination of Dithioketene Acetals: An Easy Route To Cyclic Amino Acid Derivatives
  作者：Hai-Chao Xu、Kevin D. Moeller

  DOI：10.1021/ol102193x

  日期：2010.11.19

  Catalytic intramolecular hydroamination of dithioketene acetals was developed for the synthesis of cyclic amino acid derivatives. Triggered by the addition of a catalytical amount of n-BuLi, the reaction proceeds to give proline and pipecolic acid derivatives in excellent yields and diastereoselectivity.

  二硫乙烯酮缩醛的催化分子内加氢胺化作用被开发用于合成环状氨基酸衍生物。通过添加催化量的n- BuLi触发，反应继续以优异的产率和非对映选择性得到脯氨酸和哌啶酸衍生物。
• MOSS, WILLIAM O.;BRADBURY, ROBERT H.;HALES, NEIL J.;GALLAGHER, TIMOTHY, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 51-53
  作者：MOSS, WILLIAM O.、BRADBURY, ROBERT H.、HALES, NEIL J.、GALLAGHER, TIMOTHY

  DOI：——

  日期：——