2-benzyl-2-phenyl-1,3-dithiolane | 88142-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-benzyl-2-phenyl-1,3-dithiolane
• CAS: 88142-08-9
• 化学式: C₁₆H₁₆S₂
• 分子量: 272.435
• InChiKey: RGDIOAYEACHRMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  416.6±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-benzyl-2-phenyl-1,3-dithiolane 在 1,3-二溴-5,5-二甲基海因 、 六氟丙烯 、 二乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以81%的产率得到(1,1-二氟-2-苯基乙基)苯
  参考文献：
  名称：

  宝石-用六氟丙烯-二乙胺试剂和N-碘琥珀酰亚胺或1,3-二溴-5,5-二甲基乙内酰脲对1,3-二硫杂环戊烷进行二氟化

  摘要：

  通过用六氟丙烯-二乙胺/ 1，3-二溴-5，5-二甲基乙内酰脲或N-碘代琥珀酰亚胺/水处理，可以容易地由1，3-二硫杂环戊烷以高收率制备宝石-二氟化合物。

  DOI：

  10.1016/0022-1139(94)03187-5
• 作为产物：
  描述：

  二苯基乙酮 、 1,2-乙二硫醇 在 四氯化钛 作用下， 以 氯仿 为溶剂， 生成 2-benzyl-2-phenyl-1,3-dithiolane
  参考文献：
  名称：

  Stereochemistry of the homolytic heterocyclization of alkynes with 1,2-ethanedithol into 1,4-dithianes

  摘要：

  The homolytic heterocyclization of dialkyl- and diaryl-acetylenes with 1,2-ethanedithiol leads stereoselectively to cis-2,3-disubstituted 1,4-dithianes. The stereochemistry of the reactions is determined by a combination of homolytic trans addition at the triple bond and intramolecular homolytic cis addition at the double bond. The main product of the heterocyclization of dimethyl acetylenedicarboxylate is dimethyl 5,6-dihydro-1,4-dithiin-2,3-dicarboxylate.

  DOI：

  10.1007/bf01172266

文献信息

• Reactivity of Ethanediyl<i>S,S</i>-Acetals; 2. Synthesis of 2,3-Dihydro-1,4-dithiins
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo

  DOI：10.1055/s-1991-26427

  日期：——

  A new, reliable one-step synthesis of 2,3-dihydro-1,4-dithiins from ethanediyl S,S-acetal derivatives of carbonyl compounds is reported.

  报道了一种新颖、可靠的一步合成方法，可以从醛酮化合物的乙烯二基S,S-缩醛衍生物合成2,3-二氢-1,4-二硫烯。
• Ring Expansion Reaction of 1,3-Dithiolanes and 1,3-Oxathiolanes Using Tellurium Tetrachloride
  作者：Hiroyuki Tani、Tokuo Inamasu、Rui Tamura、Hitomi Suzuki

  DOI：10.1246/cl.1990.1323

  日期：1990.8

  On treatment with tellurium tetrachloride in dichloromethane at room temperature, 1,3-dithiolanes and 1,3-oxathiolanes undergo smooth ring expansion to give dihydro-1,4-dithiin and dihydro-1,4-oxathiin derivatives respectively in good to moderate yields.

  在室温下使用氯化四碲 treatment，1,3-二噻环烷和1,3-氧噻环烷在二氯甲烷中平滑地环扩展，分别得到二氢-1,4-二噻并和二氢-1,4-氧噻并，产率从良好到适中。
• The Lithium Diisopropylamide-induced Fragmentation of 1,3-Dithiolane Derivatives of Several Ketones Having α-Hydrogen
  作者：Hideyuki Ikehira、Shigeo Tanimoto、Tatsuo Oida

  DOI：10.1246/bcsj.56.2537

  日期：1983.8

  The reaction of 1,3-dithiolane derivatives of ketones having α-hydrogen with lithium diisopropylamide results in fragmentation to the corresponding thioketone followed by further conversion in a few steps to the other intermediate species which, on trapping with alkyl halide, leads to a vinylic sulfide and/or a sulfide bearing a secondary alkyl group.

  具有 α-氢的酮的 1,3-二硫杂环戊烷衍生物与二异丙基氨基锂的反应导致裂解为相应的硫酮，然后在几个步骤中进一步转化为其他中间体物种，在用烷基卤化物捕获时，产生乙烯基硫化物和/或带有仲烷基的硫化物。
• Novel coupling of dithioacetals with Grignard reagents
  作者：Zhi-Jie Ni、Tien-Yau Luh

  DOI：10.1039/c39870001515

  日期：——

  Dithioacetals react with Grignard reagents in the presence of a catalytic amount of [NiCl2(PPh3)2] to give the corresponding olefinic coupling products in good yields; a mechanism for the reaction is suggested.

  在催化量的[NiCl 2（PPh 3）2 ]存在下，二硫缩醛与格氏试剂反应，以高收率得到相应的烯烃偶联产物。建议了一种反应机理。
• Nickel-catalyzed olefination of cyclic benzylic dithioacetals by Grignard reagents. Scope and mechanism
  作者：Zhi Jie Ni、Nai Wen Mei、Xian Shi、Yih Ling Tzeng、Maw Cherng Wang、Tien Yau Luh

  DOI：10.1021/jo00012a043

  日期：1991.6

  The details of the first nickel-catalyzed olefination of cyclic dithioacetals to form substituted styrenes and aryl-substituted 1,4-pentadienes are described. The reaction represents a new synthetic use of the dithioacetal functionality. Only nickel complexes catalyzed these cross-coupling reactions; palladium complexes displayed no catalytic activity under the reaction conditions employed. Selective coupling occurred. A mechanism for the reaction is proposed. The experimental evidence indicates that, in these nickel-catalyzed couplings, cyclic dithioacetals are more reactive than their acyclic analogues. This increased reactivity appears to be the result of maintaining the two sulfur atoms in close proximity to each other by the use of a short chain of methylene groups.