2-(5-Acetoxypentan-1-yl)-1,3-dithiane | 118794-73-3

• 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-Acetoxypentan-1-yl)-1,3-dithiane
• 英文别名: 5-(1,3-Dithian-2-yl)pentyl acetate
• CAS: 118794-73-3
• 化学式: C₁₁H₂₀O₂S₂
• 分子量: 248.411
• InChiKey: BJPJMGKTYGPUOI-UHFFFAOYSA-N

物化性质

• 沸点：
  342.4±22.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-Acetoxypentan-1-yl)-1,3-dithiane 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到6-acetoxy-1-hexanal
  参考文献：
  名称：

  温和的化学选择方案，用于去除由Dess-Martin高碘烷介导的硫代缩酮和硫缩醛。

  摘要：

  [反应：见正文]本文介绍了使用Dess-Martin高碘烷（DMP）试剂去除硫缩醛和硫缩酮的有用方法的开发。与现有方法相比，该协议具有一般的反应性，与各种官能团的相容性以及方便的反应时间。还讨论了化学选择性实验，涉及的功能可能会被DMP氧化，底物对水解速率的定性影响以及硫代乙缩醛向乙缩醛的直接转化。

  DOI：

  10.1021/ol027518n
• 作为产物：
  描述：

  6-acetoxyhexanol 在 dibutylstannanediyl bis(trifluoromethanesulfonate) pyridinium chlorochromate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 生成 2-(5-Acetoxypentan-1-yl)-1,3-dithiane
  参考文献：
  名称：

  Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates

  摘要：

  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.

  DOI：

  10.1021/jo00070a038

文献信息

• Activation and synthetic applications of thiostannanes. Conversion of aldehydes and acetals into 1,3-dithianes with high chemodifferentiation
  作者：Tsuneo Sato、Enji Yoshida、Takamichi Kobayashi、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)80396-2

  日期：1988.1

  Novel method for transforming aldehydes and acetals into 1,3-dithianes has been achieved with the aid of organotin thioalkoxides and organotin triflates. Under these reaction conditions, various acid-sensitive groups are tolerated. Differentiation between aromatic or aliphatic aldehydes and acetals has been realized.

  借助于有机锡硫代醇盐和有机锡三氟甲磺酸酯，已经实现了将醛和乙缩醛转化为1，3-二硫杂环己烷的新方法。在这些反应条件下，可以耐受各种酸敏感性基团。已经实现了芳族或脂族醛与缩醛之间的区分。
• A simple method of dethioacetalization
  作者：Gilbert Stork、Kang Zhao

  DOI：10.1016/s0040-4039(00)95181-5

  日期：1989.1
• STORK, GILBERT;ZHAO, KANG, TETRAHEDRON LETT., 30,(1989) N, C. 287-290
  作者：STORK, GILBERT、ZHAO, KANG

  DOI：——

  日期：——
• SATO, TSUNEO;YOSHIDA, ENJI, KOBAYASHI TAKAMICHI;OTERA, JUNZO;NOZAKI, HITO+, TETRAHEDRON EDRON LETT., 29,(1988) N 32, C. 3971-3974
  作者：SATO, TSUNEO、YOSHIDA, ENJI, KOBAYASHI TAKAMICHI、OTERA, JUNZO、NOZAKI, HITO+

  DOI：——

  日期：——