2-(2-bromophenyl)-1,3-dithiolane | 113509-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-bromophenyl)-1,3-dithiolane
• 英文别名: 1,3-Dithiolane, 2-(2-bromophenyl)-
• CAS: 113509-22-1
• 化学式: C₉H₉BrS₂
• 分子量: 261.206
• InChiKey: HQOUJFQRGCDKRL-UHFFFAOYSA-N

物化性质

• 沸点：
  340.0±42.0 °C(Predicted)
• 密度：
  1.554±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(2-bromophenyl)-1,3-dithiolane 在 silica gel 、 ferric nitrate 作用下， 以 正己烷 为溶剂， 反应 0.17h， 生成 邻溴苯甲醛
  参考文献：
  名称：

  DETHIOACETALIZATION OF DITHIOLANES WITH FERRIC NITRATE AND SILICA GEL IN HEXANE

  摘要：

  DOI：

  10.1080/00304949709355223
• 作为产物：
  描述：

  1,2-乙二硫醇 、 邻溴苯甲醛 在 1-丁基-3-甲基咪唑溴盐 作用下， 反应 0.33h， 以85%的产率得到2-(2-bromophenyl)-1,3-dithiolane
  参考文献：
  名称：

  离子液体[bmim] Br为可循环催化介质的羰基化合物化学选择性硫代乙酰化研究

  摘要：

  已经制备了基于1-正丁基-3-甲基咪唑鎓阳离子的离子液体，并将其用作羰基化合物的化学选择性硫缩醛化的有效催化介质。此外，已经证明了该离子液体介质的再循环和再利用。此外，使用这种催化介质不仅避免了废物的产生，而且还提供了危害最小的绿色工艺。

  DOI：

  10.1002/adsc.200303171

文献信息

• Transition metal promoted reactions. 30. Cyclopropyl anion as an allyl anion synthon. Novel synthesis of butadienes by nickel-catalyzed coupling of cyclopropyl Grignard reagents with dithioacetals
  作者：Dennis K. P. Ng、Tien Yau Luh

  DOI：10.1021/ja00207a029

  日期：1989.12

  Resolution of the reaction mixture and isolation of the triester product can be accomplished by using HPLC (4.6 X 250 mm Hypersil-ODS with 0.02 M KH2P04, pH 5.5, and a methanol gradient). Modification of the phosphorothioate was observed to be more efficient for the single-stranded d[CGCA(s)AAAAAGCG] fragment than the self-complementary eicosomer, d[CGTACTAGTT(s)AACTAGTACG] . This difference in reactivity

  反应混合物的拆分和三酯产物的分离可以通过使用HPLC（4.6 X 250 mm Hypersil-ODS，具有0.02 M KH 2 PO 4 ，pH 5.5和甲醇梯度）来完成。观察到硫代磷酸酯的修饰对于单链 d[CGCA(s)AAAAAGCG] 片段比自身互补的低分子异构体 d[CGTACTAGTT(s)AACTAGTACG] 更有效。当反应混合物在 50 ℃加热时，这种反应性差异被部分克服。在不存在硫代磷酸二酯的情况下，使用天然寡脱氧核苷酸的对照反应不会产生任何显着的标记。'2未标记的十二聚体螺旋，d [CGCA(s) AAAAAGCG].d[CGCTTTTTTGCG]，表现出的 T 为 55" C，这与 T 无法区分，PROXYL 标记（图 1 中的 a）或药物标记（图 1 中的 b）螺旋获得的值。与未标记的片段（T ，= 67”C）相比，具有两个标记的自身互补的ε-异构体 d[CG
• Ni, Zhi-Jie; Yang, Pin-Fan; Ng, Dennis K. P., Journal of the American Chemical Society, 1990, vol. 112, # 25, p. 9356 - 9364
  作者：Ni, Zhi-Jie、Yang, Pin-Fan、Ng, Dennis K. P.、Tzeng, Yih-Ling、Luh, Tien-Yau

  DOI：——

  日期：——
• 1,3,4-Thiadiazol-2-ylphenyl-1,2,4,5-tetrazines: efficient synthesis via Pinner reaction and their luminescent properties
  作者：Anna Maj、Agnieszka Kudelko、Marcin Swiatkowski

  DOI：10.24820/ark.5550190.p011.476

  日期：——
• 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.
• Intramolecularly Sulfur-Stabilized Silicon Cations as Lewis Acid Catalysts
  作者：Volker H. G. Rohde、Phillip Pommerening、Hendrik F. T. Klare、Martin Oestreich

  DOI：10.1021/om500570d

  日期：2014.7.14

  The synthesis and spectroscopic characterization of previously unprecedented sulfur-stabilized silicon cations are reported. Several 1,3-dithiolan-2-yl- and 1,3-dithian-2-yl-substituted silanes were prepared and successfully transformed into the corresponding silicon cations by hydride abstraction. The silicon-sulfur interaction creates three consecutive stereocenters at three different elements. It is remarkable that the present stereocenter at the silicon atom determines the stereochemical outcome at the formerly prochiral sulfur and carbon atoms with excellent diastereoselectivity. All sulfur-stabilized silicon cations are shown to be potent catalysts in a challenging Diels-Alder reaction. Moreover, structurally related oxazoline-stabilized silicon cations were generated and characterized but found to be unreactive.