2-prop-1-enyl-1,3-dithiolane | 61685-38-9

• 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-prop-1-enyl-1,3-dithiolane
• 英文别名: 2-(Prop-1-en-1-yl)-1,3-dithiolane
• CAS: 61685-38-9
• 化学式: C₆H₁₀S₂
• 分子量: 146.277
• InChiKey: SMYVRWWDRWWULL-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 5 Torr)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-prop-1-enyl-1,3-dithiolane 在 水 作用下， 以 乙醇 为溶剂， 以89%的产率得到丁烯-2-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 、 丁烯-2-醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以94%的产率得到2-prop-1-enyl-1,3-dithiolane
  参考文献：
  名称：

  2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为羰基化合物二硫代缩醛化和氧硫代缩醛化以及转二硫代缩醛化反应的有效催化剂

  摘要：

  使用 2,4,4,6-四溴-2,5-环己二烯酮 (TABCO)、N-溴代琥珀酰亚胺 (NBS) 和溴作为有效催化剂将羰基化合物转化为环状和无环二硫缩醛和 1,3-描述了在温和反应条件下的硫杂环戊烷。这些催化剂还用于在硫醇存在下以高产率有效地将缩醛、二缩醛、缩酮、酰基、烯胺、腙和肟转二硫缩醛。

  DOI：

  10.1080/10426500211712

文献信息

• 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。
• Selective Catalytic Transesterification, Transthiolesterification, and Protection of Carbonyl Compounds over Natural Kaolinitic Clay
  作者：Datta E. Ponde、Vishnu H. Deshpande、Vivek J. Bulbule、Arumugam Sudalai、Anil S.Gajare

  DOI：10.1021/jo971404l

  日期：1998.2.1

  Transesterification and transthiolesterification of beta-keto esters with variety of alcohols and thiols and selective protection of carbonyl functions with various protecting groups catalyzed by natural kaolinitic clay are described. The clay has been found to be an efficient catalyst in transesterifying long chain alcohols, unsaturated alcohols, and phenols to give their corresponding beta-keto esters in high yields. For the first time, transthiolesterification of beta-keto esters with a variety of thiols has been achieved under catalytic conditions. Clay also catalyzes selective transesterification of beta-keto esters by primary alcohols in the presence of secondary and tertiary alcohols giving corresponding beta-keto esters. A systematic study involving the reactivity of different nucleophiles (alcohols, amines, and thiols) toward beta-keto esters is also described. Sterically hindered carbonyl groups as well as alpha,beta-unsaturated carbonyl groups underwent protection without the deconjugation of the double bond. Chemoselective protection of aldehydes in the presence of ketones has also been achieved over natural kaolinitic clay.
• Selective protection of carbonyl compounds. Silica gel treated with thionyl chloride as an effective catalyst for thioacetalization
  作者：Yasuhiro Kamitori、Masaru Hojo、Ryoichi Masuda、Tadashi Kimura、Tatsushi Yoshida

  DOI：10.1021/jo00359a009

  日期：1986.5
• Sabde; Naik; Hegde, Journal of Chemical Research - Part S, 1996, # 11, p. 494 - 495
  作者：Sabde、Naik、Hegde、Hegde

  DOI：——

  日期：——
• Chou, Wen-Chih; Yang, Sheng-Ann; Fang, Jim-Min, Journal of the Chemical Society. Perkin transactions I, 1994, # 5, p. 603 - 610
  作者：Chou, Wen-Chih、Yang, Sheng-Ann、Fang, Jim-Min

  DOI：——

  日期：——