(E)-2-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-dithiane | 65447-84-9

• 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: (E)-2-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-dithiane
• 英文别名: (E)-2,6-Dimethyl-1-(1,3-dithian-2-yl)-1,5-heptadiene；2-[(1E)-2,6-dimethylhepta-1,5-dienyl]-1,3-dithiane
• CAS: 65447-84-9
• 化学式: C₁₃H₂₂S₂
• 分子量: 242.45
• InChiKey: RBHYZSIGEPLTPA-ZRDIBKRKSA-N

物化性质

• 沸点：
  165 °C(Press: 0.1 Torr)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-dithiane 、 叔丁基二甲基氯硅烷 、 正丁基锂 生成 (E)-2-<(tert-butyl)dimethylsilyl>-2-(2',6'-dimethyl-1,'5'-heptadienyl)-1,3-dithiane
  参考文献：
  名称：

  SCHELLER M. E.; IWASAKI G.; FREI B., HELV. CHIM. ACTA, 69,(1986) N 6, 1378-1394

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-丙二硫醇 、 (E)-3,7-二甲基-2,6-辛二烯醛 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以93%的产率得到(E)-2-(2',6'-dimethyl-1',5'-heptadienyl)-1,3-dithiane
  参考文献：
  名称：

  一种由醛和酮制备 1,3-二硫杂环戊烷的温和有效方法

  摘要：

  本文介绍了一种从醛和酮制备 1,3-二噻烷的温和方法。通过使用高氯酸锂作为路易斯酸和丙烷-1,3-二硫醇，即使是高酸性δ-羟基醛也能转化为相应的硫代乙醛。所需产品的收率为 41-98%。

  DOI：

  10.1055/s-2000-6226

文献信息

• Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1021/jo00070a038

  日期：1993.8

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.
• SCHELLER M. E.; IWASAKI G.; FREI B., HELV. CHIM. ACTA, 69,(1986) N 6, 1378-1394
  作者：SCHELLER M. E.、 IWASAKI G.、 FREI B.

  DOI：——

  日期：——
• A Mild and Efficient Method for the Preparation of 1,3-Dithianes from Aldehydes and Ketones
  作者：Lutz F. Tietze、Berthold Weigand、Christian Wulff

  DOI：10.1055/s-2000-6226

  日期：——

  A mild method for the preparation of 1,3-dithianes from aldehydes and ketones is described. By using lithium perchlorate as Lewis acid and propane-1,3-dithiol even highly acid-labile β-hydroxy aldehydes can be transformed into the corresponding thioacetals. The desired products were obtained in 41-98% yield.

  本文介绍了一种从醛和酮制备 1,3-二噻烷的温和方法。通过使用高氯酸锂作为路易斯酸和丙烷-1,3-二硫醇，即使是高酸性δ-羟基醛也能转化为相应的硫代乙醛。所需产品的收率为 41-98%。