1-(4-[1,3]Dithiolan-2-yl-phenyl)-ethanone | 101033-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-[1,3]Dithiolan-2-yl-phenyl)-ethanone
• 英文别名: 1-[4-(1,3-Dithiolan-2-yl)phenyl]ethanone
• CAS: 101033-05-0
• 化学式: C₁₁H₁₂OS₂
• 分子量: 224.348
• InChiKey: AZDLIIYHKWBEIV-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  388.9±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙酰苯甲醛 、 1,2-乙二硫醇 在 1-(4-sulfonylbutyl)triethylammonium p-toluenesulfonate 作用下， 反应 0.02h， 以90%的产率得到1-(4-[1,3]Dithiolan-2-yl-phenyl)-ethanone
  参考文献：
  名称：

  An Efficient Method for Chemoselective Thioacetalization of Aldehydes in the Presence of a Catalytic Amount of Acidic Ionic Liquid under Solvent-Free Conditions

  摘要：

  合成了一种具有烷基磺酸基团的水稳定型Brønsted酸性离子液体。该离子液体催化硫缩醛化反应顺利进行，以极佳的产率和较短的时间得到1,3-二硫杂环戊烷。本文描述了一种在离子液体（2摩尔%）催化下缓和且化学选择性保护各种醛的硫缩醛化方法。

  DOI：

  10.1055/s-0029-1217550

文献信息

• An Efficient Method for Chemoselective Thioacetalization of Aldehydes in the Presence of a Catalytic Amount of Acidic Ionic Liquid under Solvent-Free Conditions
  作者：Abdol Hajipour、Ghobad Azizi、Arnold Ruoho

  DOI：10.1055/s-0029-1217550

  日期：2009.7

  A water-stable Brønsted acidic ionic liquid with an alkane sulfonic acid group was synthesized. This ionic liquid catalyzed the thioacetalization reaction smoothly to afford 1,3-dithianes in excellent yield and less time. In this article we describe a mild and chemoselective thioacetalization procedure for the protection of various aldehydes in the presence of catalytic amount of ionic liquid (2 mol%).

  合成了一种具有烷基磺酸基团的水稳定型Brønsted酸性离子液体。该离子液体催化硫缩醛化反应顺利进行，以极佳的产率和较短的时间得到1,3-二硫杂环戊烷。本文描述了一种在离子液体（2摩尔%）催化下缓和且化学选择性保护各种醛的硫缩醛化方法。
• A Simple and Efficient Heterogeneous Procedure for Thioacetalization of Aldehydes and Ketones
  作者：Mohammed Hashmat Ali、Maria Goretti Gomes

  DOI：10.1055/s-2005-865303

  日期：——

  A new procedure for the protection of aldehydes and ketones as thioacetals promoted by catalytic amount of p-toluene-sulfonic acid and silica gel has been developed. This procedure offers versatility, short reaction time,excellent yield, good selectivity, and flexibility in terms of choice of solvent that can be utilized in this reaction. The procedure is easy to carry out and does not require aqueous

  已经开发了一种通过催化量的对甲苯磺酸和硅胶促进作为硫缩醛保护醛和酮的新方法。该程序提供了多功能性、反应时间短、产率高、选择性好以及在选择可用于该反应的溶剂方面的灵活性。该程序易于执行，不需要水处理。在大多数情况下，简单的过滤然后去除溶剂会产生纯产品。
• Molten Salt as a Green Reaction Medium: Efficient and Chemoselective Dithioacetalization and Oxathioacetalization of Aldehydes Mediated by Molten Tetrabutylammonium Bromide
  作者：Brindaban C. Ranu、Arijit Das

  DOI：10.1071/ch03318

  日期：——

  Tetrabutylammonium bromide in the molten state has been demonstrated to be a very efficient catalyst and reaction medium for the highly chemoselective dithioacetalization and oxathioacetalization of aldehydes. The tetrabutylammonium bromide is recycled for subsequent reactions.

  熔融状态的四丁基溴化铵已被证明是一种非常有效的催化剂和反应介质，可用于醛的高化学选择性二硫代缩醛化和氧硫代缩醛化。四丁基溴化铵被循环用于后续反应。
• Pr(OTf)₃ as an Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Aldehydes
  作者：Surya De

  DOI：10.1055/s-2004-834858

  日期：——

  Praseodymium triflate has been found to be an efficient and recyclable catalyst for chemoselective protection of aldehydes.

  三氟甲磺酸镨已被发现是一种高效且可循环的催化剂，适用于醛的选择性保护反应。
• Copper(II) tetrafluoroborate as an extremely efficient catalyst for 1,3-dithiolane/dithiane formation from carbonyl compounds under solvent-free conditions at room temperature
  作者：Ram C. Besra、Santosh Rudrawar、Asit K. Chakraborti

  DOI：10.1016/j.tetlet.2005.07.059

  日期：2005.9

  formation from aromatic, heteroaromatic and aliphatic aldehydes and cyclic saturated ketones in 1–5 min under solvent-free conditions at room temperature. The reaction is compatible with other functionalities such as ether, ester, hydroxyl, halide, nitro and cyano groups and exhibits excellent chemoselectivity. α,β-Unsaturated aldehydes/ketones lead to selective formation of 1,3-dithiolanes instead of

  四氟硼酸铜（II）水合物是一种新型且极其有效的催化剂，在室温下无溶剂条件下，可在1-5分钟内由芳族，杂芳族和脂肪族醛类和环状饱和酮形成1,3-二硫杂环戊烷/二硫杂环丁烷。该反应与其他官能团如醚，酯，羟基，卤化物，硝基和氰基相容，并显示出优异的化学选择性。α，β-不饱和醛/酮可导致选择性形成1,3-二硫杂环戊烷而不是迈克尔加成产物。对于带有醛和酮羰基的底物，与醛发生化学选择性的二硫杂环戊烷。