2-methyl-2-pentyl-1,3-dithiolane | 81979-61-5

• 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-methyl-2-pentyl-1,3-dithiolane
• CAS: 81979-61-5
• 化学式: C₉H₁₈S₂
• 分子量: 190.374
• InChiKey: HLRYPNJDWGDQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  4
• 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-methyl-2-pentyl-1,3-dithiolane 在 三氯化铁 、 potassium iodide 作用下， 以 甲醇 为溶剂， 反应 5.5h， 以90%的产率得到2-庚酮
  参考文献：
  名称：

  FeCl3/KI 对二硫缩醛的轻松脱保护

  摘要：

  摘要 羰基化合物由相应的二硫缩醛以FeCl3/KI和甲醇为溶剂回流再生。

  DOI：

  10.1081/scc-120016345
• 作为产物：
  描述：

  2-庚酮 、 2,2-dibutyl-1,3,2-dithiastannolane 在 dibutylstannanediyl bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 以74%的产率得到2-methyl-2-pentyl-1,3-dithiolane
  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

• A Facile Deprotection of Dithioacetals by FeCl₃/KI
  作者：Subhash P. Chavan、Priti B. Soni、Ramesh R. Kale、K. Pasupathy

  DOI：10.1081/scc-120016345

  日期：2003.1.4

  Abstract Carbonyl compounds were regenerated from corresponding dithioacetals via refluxing with FeCl3/KI and methanol as a solvent.

  摘要 羰基化合物由相应的二硫缩醛以FeCl3/KI和甲醇为溶剂回流再生。
• Zirconium(IV) chloride-silica catalysed thioacetalisation of carbonyl compounds
  作者：Harish K Patney、Simon Margan

  DOI：10.1016/0040-4039(96)00892-1

  日期：1996.6

  Anhydrous anhydrous zirconium(IV) chloride dispersed on silica gel efficiently thioacetalised a variety of carbonyl compounds in near quantitative yields

  分散在硅胶上的无水无水氯化锆可以以接近定量的收率有效地硫代乙酰化各种羰基化合物
• AN EFFICIENT METHOD FOR THE THIOACETALIZATION OF CARBONYL COMPOUNDS IN THE PRESENCE OF CATALYTIC AMOUNTS OF BENZYLTRIPHENYLPHOSPHONIUM TRIBROMIDE
  作者：A. R. Hajipour、S. A. Pourmousavi、A. E. Ruoho

  DOI：10.1080/00304940709458596

  日期：2007.8

  in multi-step syntheses. Among carbonyl protecting groups, dithioacetals constitute an important class of compounds as acyl anion equivalents' or masked methylene functions in carbon-carbon bond forming reactions. They are versatile2 due to their straightforward preparation and also to their stability under basic or mildly acidic conditions. Although several methods have been reported for protection

  在多步合成中通常需要保护羰基。在羰基保护基团中，二硫代缩醛构成了一类重要的化合物，作为酰基阴离子等价物或碳-碳键形成反应中的掩蔽亚甲基官能团。由于其制备简单，并且在碱性或弱酸性条件下具有稳定性，因此它们用途广泛2。虽然已经报道了几种方法来保护羰基化合物作为二硫代缩醛，3-I7，但其中许多方法都有一定的局限性，例如产率低、反应条件苛刻、反应时间长和试剂昂贵。因此，仍然需要更温和、更简单和更有效的替代方案来保护羰基化合物。该试剂是通过在室温下将 Oxone (2KHSOs*KHS04*K2SO4) 的水溶液滴加到苄基三苯基溴化鏻和 NaBr 的水溶液中来合成的，得到黄色沉淀的定量收率，该沉淀在 279 nm 典型的三溴化物。18 试剂 1 易于处理，非常稳定，可以在工作台上存放数月而不会失去其活性。该试剂是在二氯甲烷中将羰基化合物转化为相应二硫代缩醛的有效催化剂，也是在酮存在下将醛转化为相应二
• An Efficient Method for Thioacetalization of Carbonyl Compounds in the Presence of a Catalytic Amount of Benzyltriphenylphosphonium Tribromide Under Solvent-Free Conditions
  作者：Abdol R. Hajipour、Seied A. Pourmousavi、Arnold E. Ruoho

  DOI：10.1080/10426500601088739

  日期：2007.3.15

  variety of carbonyl compounds have been successfully converted to the corresponding thioacetal derivatives in good to excellent yields on the reaction of carbonyl compounds with 1,2-ethanedithiole, 1,3-propanedithiol, and ethanethiol in the presence of catalytic amount of benzyltriphenylphosphonium tribromide under solvent-free conditions. Some of the major advantages of this method are mild reaction conditions

  在催化量的三溴化苄基三苯基鏻存在下，羰基化合物与 1,2-乙二硫醇、1,3-丙二硫醇和乙硫醇的反应已成功地转化为相应的硫代缩醛衍生物无溶剂条件。这种方法的一些主要优点是反应条件温和、效率高以及与其他报道的方法兼容。此外，在这些实验条件下，双键或酮位的 α 位，甚至芳环中都不会发生溴化。
• Silicasulfuric Acid/NaNO₃ as a New Reagent for the Deprotection of <i>S</i>,<i>S</i>-Acetals under Mild Conditions
  作者：Abdol Hajipour、Amin Zarei、Leila Khazdooz、Arnold Ruoho

  DOI：10.1055/s-2006-926431

  日期：2006.5

  An efficient, mild and chemoselective method for the deprotection of S,S-acetal compounds to their corresponding car­bonyl compounds using silicasulfuric acid/NaNO3 is reported.

  报道了一种高效、温和且化学选择性的方法，用于将S,S-缩醛化合物去保护为其相应的羰基化合物，该方法采用硅硫酸/硝酸钠体系。