2-Butyl-2-methyl-1,3-dithiane | 150237-23-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-Butyl-2-methyl-1,3-dithiane
• 英文别名: 2-butyl-2-methyl-1,3-dithian；1,3-Dithiane, 2-butyl-2-methyl-
• CAS: 150237-23-3
• 化学式: C₉H₁₈S₂
• 分子量: 190.374
• InChiKey: VYCYDDZQKIGEFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-Butyl-2-methyl-1,3-dithiane 以100%的产率得到(1R,2R)-2-Butyl-2-methyl-[1,3]dithiane 1-oxide
  参考文献：
  名称：

  真菌酶促氧化硫缩醛中前手性硫代烷基的立体选择性

  摘要：

  在蠕虫属菌种的培养物中2-取代的1,3-二硫杂环丁烷的酶促氧化显示赤道氧化和（1 S）-单亚砜产物的立体异构。

  DOI：

  10.1039/c39830000282
• 作为产物：
  描述：

  2-己酮 、 3-(1,3-二噻烷-2-亚基)-2,4-戊二酮 在 盐酸 作用下， 反应 0.92h， 以88%的产率得到2-Butyl-2-methyl-1,3-dithiane
  参考文献：
  名称：

  Chemoselective Thioacetalization Using 3-(1,3-Dithian-2-ylidene)pentane-2,4-dione as an Odorless and Efficient Propane-1,3-dithiol Equivalent under Solvent-Free Conditions

  摘要：

  作为一种非硫醇和无气味的丙烷-1,3-二硫醇等效物，3-(1,3-二噻烯-2-亚基)戊烯-2,4-二酮在无溶剂条件下的酸催化下进行了硫缩醛化研究。多种选定的醛和脂肪酮被高产率转化为相应的二硫缩醛。芳香酮相对较慢的反应速率使得对芳香醛或脂肪酮的选择性保护成为可能，而不仅仅是芳香酮。

  DOI：

  10.1055/s-2006-950298

文献信息

• Entirely Solvent-Free Procedure for the Synthesis of Distillable 1,3-Dithianes Using Lithium Tetrafluoroborate as a Reusable Catalyst
  作者：Tsuneo Sato、Kiyoshi Kazahaya、Shinya Tsuji

  DOI：10.1055/s-2004-829084

  日期：——

  Treatment of various types of aldehydes and ketones with 1,3-propanedithiol in the presence of a catalytic amount of lithium tetrafluoroborate at 25 °C under solvent-free conditions followed by direct purification by distillation of the resulting mixture affords the corresponding 1,3-dithianes in good to excellent yields. Chemoselective protection of keto aldehydes is also successfully achieved over the catalyst. The catalyst can be recovered and reused.

  在无溶剂条件下，将各种类型的醛和酮与1,3-丙二硫醇在催化量的四氟硼酸锂存在下于25°C反应，然后通过直接蒸馏所得混合物进行直接纯化，可以获得相应的1,3-二硫烷，产率为良好至优秀。该催化剂还能成功实现酮醛的选择性保护。催化剂可以回收并重复使用。
• Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent
  作者：Haifeng Yu、Dewen Dong、Yan Ouyang、Qun Liu

  DOI：10.1139/v05-184

  日期：2005.10.1

  Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.

  无味的2-(1,3-二硫杂环戊烷-2-亚基)-3-氧代丁酸(1c)被制备并研究其在羰基化合物的硫缩醛化反应中作为1,3-丙二硫醇当量的应用。结果显示，在室温或回流温度下，存在乙酰氯的情况下，各种羰基化合物2与1c的硫缩醛化反应进行得很顺利，并以高收率(高达99%)得到了相应的二硫代缩醛3。此外，硫缩醛化在醛和酮之间表现出高化学选择性。关键词：化学选择性，2-(1,3-二硫杂环戊烷-2-亚基)-3-氧代丁酸，α-氧代酮烯二硫代缩醛，1,3-丙二硫醇当量，硫缩醛化。
• Chemoselective and Odorless Transthioacetalization of Acetals Using α-Oxo-Ketene Dithioacetals as Thiol Equivalents
  作者：Hai-Feng Yu

  DOI：10.1080/00397911.2011.631075

  日期：2013.5.3

  Abstract Using α-oxo-ketene dithioacetals 1a as odorless thiol equivlents, an efficient and odorless transthioacetalization of acetals 2 has been developed. In the presence of MeCOCl in MeOH, the cleavage of 1a commences to generate thiols at both room and reflux temperatures, and the generated thiols then react with acetals 2 to give correspecting thioacetals 3 in good yield. This transthioacetalization

  摘要 使用 α-氧代-烯酮二硫代缩醛 1a 作为无味的硫醇等价物，已开发出一种有效且无味的缩醛 2 转硫缩醛化反应。在 MeOH 中存在 MeCOCl 的情况下，1a 的裂解开始在室温和回流温度下生成硫醇，然后生成的硫醇与缩醛 2 反应以良好的产率得到相应的硫缩醛 3。这种转硫缩醛化反应的特点是反应条件温和、程序简单、产率高、化学选择性好。值得注意的是，在反应和后处理过程中只能感觉到非常微弱的硫醇气味。图形概要
• 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.
• Chemoselective Thioacetalization in Water:  3-(1,3-Dithian-2-ylidene)pentane- 2,4-dione as an Odorless, Efficient, and Practical Thioacetalization Reagent
  作者：Dewen Dong、Yan Ouyang、Haifeng Yu、Qun Liu、Jun Liu、Mang Wang、Jing Zhu

  DOI：10.1021/jo050271y

  日期：2005.5.1

  A chemoselective thioacetalization utilizing 3-(1,3-dithian-2-ylidene)pentane-2,4-dione as a novel nonthiolic, odorless 1,3-propanedithiol equivalent catalyzed by p-dodecylbenzenesulfonic acid in water has been developed.