2-propyl-1,3-dithiolane | 5616-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-propyl-1,3-dithiolane
• CAS: 5616-57-9
• 化学式: C₆H₁₂S₂
• 分子量: 148.293
• InChiKey: YFPNQWYEDBOBMI-UHFFFAOYSA-N

物化性质

• 沸点：
  63-65 °C(Press: 3 Torr)
• 密度：
  1.046±0.06 g/cm3(Predicted)
• 保留指数：
  1176;1188;1202;1188

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 可旋转键数：
  2
• 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-propyl-1,3-dithiolane 在 水 作用下， 以 乙醇 为溶剂， 以86%的产率得到正丁醛
  参考文献：
  名称：

  Iodine–alumina as an efficient and useful catalyst for the regeneration of carbonyl functionality from the corresponding 1,3-oxathiolanes and 1,3-dithiolanes in aqueous system

  摘要：

  A simple and useful method has been demonstrated for the deprotection of 1,3-oxathiolanes and 1,3-dithiolanes to the corresponding carbonyl compounds in excellent yield by employing catalytic amount (30 mol %) of iodine supported on neutral alumina in ethanol-water or water. The major advantages of this protocol are mild reaction conditions, less reaction time, easy to handle, high yields, inexpensive reagent and environmentally benign. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.084
• 作为产物：
  描述：

  1,2-乙二硫醇 、 正丁醛 在 praseodymium(III) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到2-propyl-1,3-dithiolane
  参考文献：
  名称：

  Pr(OTf)₃ as an Efficient and Recyclable Catalyst for Chemoselective Thioacetalization of Aldehydes

  摘要：

  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。

  DOI：

  10.1055/s-2004-834858

文献信息

• Transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones catalysed by natural kaolinitic clay
  作者：G. K. Jnaneshwara、N. B. Barhate、A. Sudalai、V. H. Deshpande、R. D. Wakharkar、A. S. Gajare、M. S. Shingare、R. Sukumar

  DOI：10.1039/a706475f

  日期：——

  Natural kaolinitic clay efficiently catalyses the transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones with ethane-1,2-dithiol and propane-1,3-dithiol to produce the corresponding dithiolanes in high yields.

  天然高岭土能高效催化缩醛、缩酮、肟、烯胺和甲苯磺酰腙与乙二硫醇和丙三硫醇的反式双硫缩醛化反应，以高产率生成相应的二硫杂环戊烷。
• Natural kaolinitic clay: A remarkable reusable solid catalyst for the selective functional protection of aldehydes and ketones
  作者：Datta Ponde、H.B. Borate、A. Sudalai、T. Ravindranathan、V.H. Deshpande

  DOI：10.1016/0040-4039(96)00888-x

  日期：1996.6

  Natural kaolinitic clay possessing transition metals such as Fe and Ti in its lattice has been found to catalyze efficiently the chemoselective acetalization and thioacetalization of variety of carbonyl compounds with ethane-1,2-diol and ethane-1,2-dithiolrespectively.

  已经发现在其晶格中具有过渡金属例如Fe和Ti的天然高岭土粘土分别有效地催化各种羰基化合物与乙烷-1,2-二醇和乙烷-1,2-二硫醇的化学选择性缩醛化和硫代缩醛化。
• Trichloroisocyanuric Acid as a Mild and Efficient Catalyst for Thioacetalization and Transthio-acetalization Reactions
  作者：H. Firouzabadi、N. Iranpoor、H. Hazarkhani

  DOI：10.1055/s-2001-17451

  日期：——

  Trichloroisocyanuric acid (1), a cheap industrial chemical, catalyzes mild and efficient thioacetalization and transthioacetalization reactions. In addition, this catalyst is very selective for this purpose.

  三氯异氰尿酸（1），一种廉价的工业化学品，催化温和且高效的硫缩醛化和硫转移缩醛化反应。此外，该催化剂在这一用途上具有非常高的选择性。
• Ruthenium(III) Chloride-Catalyzed Thioacetalization of Carbonyl Compounds: Scope, Selectivity, and Limitations
  作者：Surya?Kanta De

  DOI：10.1002/adsc.200404323

  日期：2005.4

  A variety of carbonyl compounds can be easily and rapidly converted to the corresponding cyclic and acylic dithioacetals in the presence of a catalytic amount of ruthenium chloride in acetonitrile at room temperature. Some of the major advantages of this protocol are high chemoselectivity, operational simplicity, very short reaction times, high yields, and also compatibility with other protecting groups

  在室温下，在乙腈中催化量的氯化钌存在下，各种羰基化合物可以轻松快速地转化为相应的环状和酰基二硫缩醛。该方案的一些主要优点是化学选择性高，操作简便，反应时间短，产率高以及与其他保护基团的相容性。
• The Reaction of 2-Ethoxy-1,3-dithiolane with Carbonyl Compounds
  作者：Shigeo Jo、Shigeo Tanimoto、Tatsuo Oida、Masaya Okano

  DOI：10.1246/bcsj.54.1434

  日期：1981.5

  The reaction of 2-ethoxy-1,3-dithiolane with carbonyl compounds such as aldehydes and ketones was investigated. The reaction proceeded smoothly in the presence of the HgCl2-catalyst to afford 2-substituted and 2,2-disubstituted 1,3-dithiolanes. The reaction also offers an interesting alternative to the previously reported methods of synthesizing 1,3-dithiolanes which involve the acid-catalyzed reaction of carbonyl compounds with 1,2-ethanedithiol.

  研究了2-乙氧基-1,3-二硫烷与醛和酮等羰基化合物的反应。在HgCl2催化剂的存在下，反应顺利进行，得到2-取代和2,2-双取代的1,3-二硫烷。该反应还为合成1,3-二硫烷提供了一种有趣的替代方案，与先前报道的羰基化合物与1,2-乙二硫醇的酸催化反应方法相比。