Dioctyl trithiocarbonate | 89622-57-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: Dioctyl trithiocarbonate
• 英文别名: Bis(octylsulfanyl)methanethione
• CAS: 89622-57-1
• 化学式: C₁₇H₃₄S₃
• 分子量: 334.655
• InChiKey: FJCYOJUAUCXOQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  190-193 °C(Press: 0.3 Torr)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯磺酸正辛酯 在 二硫化碳 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以99%的产率得到Dioctyl trithiocarbonate
  参考文献：
  名称：

  An efficient, one-pot synthesis of trithiocarbonates from alcoholic tosylates using the Cs2CO3/CS2 system

  摘要：

  A single-step novel protocol for the preparation of symmetrical trithiocarbonates from a corresponding variety of primary, secondary, and tertiary alcoholic tosylates using the Cs2CO3/CS2 system, was developed. This protocol is mild and more efficient than the reported methods.

  DOI：

  10.1007/s00706-008-0956-7

文献信息

• Comparative study of the13C nuclear magnetic resonance shifts of carbonyl and thiocarbonyl compounds
  作者：Alan R. Katritzky、Stanislaw Sobiak、Charles M. Marson

  DOI：10.1002/mrc.1260260805

  日期：1988.8

  The 13C spectra of nine novel and fifteen known derivatives YC(:X)Z with X = O or S are reported and compared with literature data. Two linear relationships between 13CO and 13CS are established depending on whether or not Y or Z is linked through an O atom to the CX group. General equations for 13CO and 13CS in terms of the attached groups are also deduced. The 13C chemical shifts of n-butyl and n-octyl groups attached to the heteroatoms in this series of compounds are recorded and discussed.

  报道了九种新衍生物和十五种已知衍生物YC(:X)Z（其中X=O或S）的13C谱，并与文献数据进行比较。根据Y或Z是否通过O原子与CX基团相连，建立了两个关于13CO和13CS的线性关系。还推导出关于附着基团的13CO和13CS的一般方程。记录并讨论了这一系列化合物中连接到杂原子的n-丁基和n-辛基的13C化学位移。
• Mild and Efficient One-Step Synthesis of Trithiocarbonates Using Minimum Amount of CS₂
  作者：Takeshi Endo、Naoto Aoyagi、Bungo Ochiai、Hideharu Mori

  DOI：10.1055/s-2006-932480

  日期：——

  Symmetrical dialkyl trithiocarbonates were obtained from various alkyl halides with an equivalent of carbon disulfide and cesium carbonate in polar aprotic solvents, although the conventional synthesis of trithiocarbonates had required large excess amount of carbon disulfide. This reaction proceeds under ambient conditions, for example, at room temperature under an aerial atmosphere, without strong

  尽管三硫代碳酸酯的常规合成需要大量过量的二硫化碳，但在极性非质子溶剂中，由各种烷基卤化物与等量的二硫化碳和碳酸铯得到对称的二烷基三硫代碳酸酯。该反应在环境条件下进行，例如在室温和大气气氛下，没有强碱和相转移催化剂。
• Superbasic system CsOH/DMSO as a reagent for a fast one-step synthesis of symmetrical dialkyl trithiocarbonates
  作者：Ali Yousefi

  DOI：10.1080/17415993.2015.1079912

  日期：2015.11.2

  Symmetrical dialkyl trithiocarbonates were readily synthesized in excellent yields by one-step reaction of carbon disulfide and various alkyl halides under mild reaction conditions in the presence of cesium hydroxide as a super basic system. This method provides a synthesis of symmetrical dialkyl trithiocarbonates in short reaction times without the use of highly toxic starting materials. GRAPHICAL

  在氢氧化铯作为超碱性体系存在下，在温和的反应条件下，通过二硫化碳和各种烷基卤化物的一步反应，可以很容易地以优异的收率合成对称的二烷基三硫代碳酸酯。该方法提供了在短反应时间内合成对称的三硫代碳酸二烷基酯，而无需使用剧毒的起始材料。图形概要
• A Facile KF/Al₂O₃-mediated, One-pot Synthesis of Symmetrical Trithiocarbonates from Alkyl Halides and Carbon Disulfide
  作者：Barahman Movassagh、Mohammad Soleiman-Beigi、Mohammad Nazari

  DOI：10.1246/cl.2008.22

  日期：2008.1.5

  A facile, efficient, and convenient method has been developed for the one-pot synthesis of symmetrical trithiocarbonates from carbon disulfide and various alkyl halides in the presence of KF/Al 2 O 3 in DMF at room temperature.

  已开发出一种简便、高效且方便的方法，用于在室温下在 DMF 中，在 KF/Al 2 O 3 存在下，由二硫化碳和各种烷基卤化物一锅法合成对称的三硫代碳酸酯。
• A Novel One-Step Synthesis of Symmetrical Dialkyl Trithiocarbonates in the Presence of Phase-Transfer Catalysis
  作者：Ali Reza Kiasat、Mehdi Fallah Mehrjardi

  DOI：10.1002/jccs.200800094

  日期：2008.6

  Symmetrical trithiocarbonates were directly obtained, in moderate to excellent isolated yields, by the reaction of various primary, secondary, allylic and benzylic halides or alkyl tosylates with a suspension of granulated KOH and alumina in CS2 under phase-transfer catalysis. In this manner, cyclic trithiocarbonates such as 1,3-dithiolane-2-thione can also be prepared without formation of any polymeric

  在相转移催化下，通过各种伯、仲、烯丙基和苄基卤化物或甲苯磺酸烷基酯与颗粒状 KOH 和氧化铝在 CS2 中的悬浮液反应，直接获得对称三硫代碳酸酯，分离产率适中至极好。以这种方式，环状三硫代碳酸酯如 1,3-二硫杂环戊烷-2-硫酮也可以在不形成任何聚合副产物的情况下制备。