2-亚甲基-1,3-二硫杂环戊烷 | 26728-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 中文名称: 2-亚甲基-1,3-二硫杂环戊烷
• 英文名称: 2-methylene-1,3-dithiolane
• 英文别名: Methylenedithiolane；2-methylene-[1,3]dithiolane；2-methylidene-1,3-dithiolane
• CAS: 26728-22-3
• 化学式: C₄H₆S₂
• 分子量: 118.224
• InChiKey: YIKPJSQNULCKHB-UHFFFAOYSA-N

物化性质

• 沸点：
  228℃
• 密度：
  1.19
• 闪点：
  105℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-亚甲基-1,3-二硫杂环戊烷 在 acid 作用下， 以 水 、 乙腈 为溶剂， 生成 ethanedithiol monoacetate
  参考文献：
  名称：

  Acid-catalyzed hydrolysis of 2-methylene-1,3-dithiolane. Complete analysis of a three-stage reaction mechanism

  摘要：

  DOI：

  10.1021/ja00335a045
• 作为产物：
  描述：

  2-methyl-1,3-dithiolan-2-yl perchlorate 在 水 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以1.5 g的产率得到2-亚甲基-1,3-二硫杂环戊烷
  参考文献：
  名称：

  Cyclic dithio-carbenium ion salts and their conversion to ketene dithioacetals

  摘要：

  DOI：

  10.1016/s0040-4039(00)87425-0

文献信息

• Isolation of Dithiolanylium Salts and Their Conversion to Ketene Dithioacetals and Ortho Esters
  作者：Tadashi Okuyama、Wataru Fujiwara、Takayuki Fueno

  DOI：10.1246/bcsj.59.453

  日期：1986.2

  prepared by the reaction of 1,2-ethanedithiol with acyl chlorides in the presence of perchloric acid. Treatments of 1 with triethylamine gave 2-alkylidene-1,3-dithiolane (2) when the 2-substituent was a primary or secondary alkyl group. 2-Aryl derivatives of 1 were converted to ortho esters by the reaction with methanol in the presence of silver nitrate. 1,3-Dithian-2-ylium perchlorates and 2-alkylidene-1

  在高氯酸的存在下，通过 1,2-乙二硫醇与酰氯的反应制备了各种 2-取代的 1,3-二硫戊环-2-鎓高氯酸盐 (1)。当 2-取代基是伯或仲烷基时，用三乙胺处理 1 得到 2-亚烷基-1,3-二硫戊环 (2)。1 的 2-芳基衍生物通过在硝酸银存在下与甲醇反应转化为原酸酯。1,3-Dithian-2-ylium 高氯酸盐和 2-alkylidene-1,3-dithianes 也类似地从 1,3-丙二硫醇制备。
• A short and efficient synthesis of ketene O,O- and S,S-acetals under focused microwave irradiation and solvent-free conditions
  作者：Angel Díaz-Ortiz、Pilar Prieto、André Loupy、David Abenhaïm

  DOI：10.1016/0040-4039(96)00110-4

  日期：1996.3

  A new methodology leading to ketene O,O- and S,S-acetals is reported. The title compounds were prepared from the corresponding halogenated precursors under microwave irradiation in the absence of solvent within 5–25 minutes with excellent yields. Yields obtained under microwaves are by far the best when compared to those obtained by ultrasound or classical heating in the same conditions of time and

  报道了导致烯酮O，O-和S，S-乙缩醛的新方法。标题化合物是由相应的卤代前体在无溶剂下于5-25分钟内在微波辐射下制备的，具有优异的收率。与在相同的时间和温度条件下通过超声或经典加热获得的产率相比，在微波下获得的产率迄今为止是最好的。
• Asymmetric [2 + 2] cycloaddition reaction catalyzed by a chiral titanium reagent
  作者：Koichi Narasaka、Yujiro Hayashi、Hideshi Shimadzu、Shigeo Niihata

  DOI：10.1021/ja00049a020

  日期：1992.11

  In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.
• Ketene Thioacetals from α-Chloromercaptals
  作者：Franco Bellesia、Monica Boni、Franco Ghelfi、Ugo M. Pagnoni

  DOI：10.1080/00397919308011176

  日期：1993.12

  Excellent yields of ketene thioacetals are obtained from 2-(1-chloroalkyl)-1,3-dithiolanes or 2-(1-chloroalkyl)-1,3-dithianes.
• Exploratory Synthetic Studies Involving the Tricyclo[9.3.0.02,8]tetradecane Ring System Peculiar to the Cyathins
  作者：Karl R. Dahnke、Leo A. Paquette

  DOI：10.1021/jo00083a034

  日期：1994.2

  Following an improved preparation of 2-methylene-1,3-dithiolane, this ketene acetal was shown to undergo inverse-electron-demand Diels-Alder cycloaddition to tropone. Regiocontrolled copper hydride reduction and resolution via sulfoximine adducts was readily achieved to give (-)-9. Addition to 9 of the chiral nonracemic vinyl bromides 21 and 22 proceeded with endo capture of the nucleophilic vinyllithium to give carbinols that underwent anionic oxy-Cope rearrangement at somewhat elevated temperatures. The [3,3] sigmatropic event delivered cis,syn,cis-tricyclo[9.3.0.0(2,8)]tetradecnones possessing structural frameworks related to the cyathins. Once 31 was in hand, it proved an easy matter to introduce added unsaturation and oxygen substituents. The tendency of certain derivatives for transannular cyclization was made quite apparent. Attempts to introduce a C(6)-alpha-methyl substituent was not achieved, chiefly as the result of the overall molecular concavity of this class of intermediates. A variety of reactions aimed at enhancing the level of functionality in rings B and C was explored and processes conducive to the attainment of these goals were developed.