1,4-二硫杂螺[4.5]癸烷 | 177-16-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 中文名称: 1,4-二硫杂螺[4.5]癸烷
• 英文名称: 1,4-dithiaspiro[4.5]decane
• CAS: 177-16-2
• 化学式: C₈H₁₄S₂
• mdl: MFCD01684021
• 分子量: 174.331
• InChiKey: CWBCHVVTDJAGBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• 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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1,4-二硫杂螺[4.5]癸烷 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以73%的产率得到环己硫醇
  参考文献：
  名称：

  Metalation of 1,3-dithiolanes. Mercaptan synthesis and carbonyl transposition

  摘要：

  DOI：

  10.1021/ja00530a043
• 作为产物：
  描述：

  环己酮二甲缩酮 在 Nafion-H 水 作用下， 以 丙酮 、 苯 为溶剂， 反应 0.5h， 生成 1,4-二硫杂螺[4.5]癸烷
  参考文献：
  名称：

  Catalysis by Solid Superacids; 8¹. Improved Nafion-H²Perfluorinated Resinsulfonic Acid-Catalyzed Preparation of Dimethyl Acetals and Ethylenedithioacetals, and Hydrolysis of Dimethyl Acetals

  摘要：

  DOI：

  10.1055/s-1981-29415

文献信息

• 2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-Bromosuccinimide (NBS) and Bromine as Efficient Catalysts for Dithioacetalization and Oxathioacetalization of Carbonyl Compounds and Transdithioacetalization Reactions
  作者：Nasser Iranpoor、Habib Firouzabadi、Hamid Reza Shaterian、M. A. Zolfigol

  DOI：10.1080/10426500211712

  日期：2002.5.1

  6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high

  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。
• 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。
• Dehydration Reactions in Water. Surfactant-type Brønsted Acid-catalyzed Dehydrative Etherification, Thioetherification, and Dithioacetalization in Water
  作者：Shu Kobayashi、Shinya Iimura、Kei Manabe

  DOI：10.1246/cl.2002.10

  日期：2002.1

  Dehydration reactions such as etherification, thioetherification, and dithioacetalization are efficiently catalyzed by a surfactant-type Bronsted acid in water.

  醚化、硫醚化和二硫代缩醛等脱水反应在水中由表面活性剂型布朗斯台德酸有效催化。
• LiBF₄ Catalyzed Chemoselective Conversion of Aldehydes to 1,3-Oxathiolanes and 1,3-Dithianes
  作者：J. S. Yadav、B. V. S. Reddy、Sushil Kumar Pandey

  DOI：10.1055/s-2001-10780

  日期：——

  Lithium tetrafluoroborate is found to be an efficient catalyst for the chemoselective protection of both aromatic and aliphatic aldehydes as 1,3-oxathiolanes and 1,3-dithianes under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.

  四氟硼酸锂被发现是一种高效的催化剂，可以在温和的反应条件下对芳香醛和脂肪醛进行化学选择性保护，生成1,3-氧硫环烷和1,3-二硫烷。由于反应条件中性，这种方法与酸敏感底物相容。
• α,α-Diacetyl Cyclic Ketene Dithioacetals: Odorless and Efficient Dithiol Equivalents in Thioacetalization Reactions
  作者：Qun Liu、Dewen Dong、Haifeng Yu、Yanbing Yin、Qunxin Fang、Jingping Zhang

  DOI：10.1055/s-2004-822892

  日期：——

  Two novel, non-thiolic, odorless dithiol equivalents, α,α-diacetyl cyclic ketene dithioacetals 2a and 2b, had been developed. A range of carbonyl compounds 3 were converted into corresponding dithioacetals, dithianes 4 and dithiolanes 5, in high yields (up to 99%) in the presence of 2a or 2b. Moreover, 2a and 2b show high chemoselectivity between aldehyde and ketone in thioacetalization.

  开发了两种新型非硫醇类、无臭的二硫醇等效物，即α,α-二乙酰环状酮烯二硫缩酮2a和2b。一系列羰基化合物3在与2a或2b的存在下，高产率（高达99%）地转化为相应的二硫缩酮4和二硫醇环5。此外，2a和2b在硫缩酮化过程中对醛和酮显示出高度的化学选择性。

表征谱图