2,2-diphenyl-1,3-dithiane | 10359-08-7

• 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-diphenyl-1,3-dithiane
• 英文别名: 2,2-diphenyl[1,3]dithiane；2,2-diphenyl-[1,3]dithiane；2,2-Diphenyl-[1,3]dithian
• CAS: 10359-08-7
• 化学式: C₁₆H₁₆S₂
• 分子量: 272.435
• InChiKey: QHKITCYPPCMIOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 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：

  2,2-diphenyl-1,3-dithiane 在 methyltriphenylphosphonium tribromide 、 水 作用下， 生成 二苯甲酮
  参考文献：
  名称：

  噻吩的1，3对二硫代苯乙缩醛脱硫缩醛

  摘要：

  三溴甲基三苯基phosph是一种有效的温和的脱硫缩酮化试剂，对2-苯基和2-乙烯基1，3-二噻烷相对于2-烷基1，3-二噻吩具有高选择性，而且所研究的底物没有任何二次溴化反应。用三溴化三甲基苯基铵也反应成功。

  DOI：

  10.1016/s0040-4039(00)84691-2
• 作为产物：
  描述：

  苯甲醛 在 potassium tert-butylate 、 碘 、 palladium diacetate 、 4,6-二(二苯基膦)吩嗪 作用下， 以 氯仿 为溶剂， 反应 27.0h， 生成 2,2-diphenyl-1,3-dithiane
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of 2-Aryl-1,3-dithianes

  摘要：

  Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and diarylmethanes are illustrated. Cross-coupling of a range of aryl dithianes with aryl bromides, including scope and current limitations, is presented.

  DOI：

  10.1021/ol502428h

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。
• Cleavage of 1,3-Dithianes via Acid-Catalyzed Hydrolysis of the Corresponding 1,3-Dithianemonooxides
  作者：Karsten Krohn、Stephan Cludius-Brandt

  DOI：10.1055/s-2008-1067164

  日期：2008.8

  The hydrolysis of 1,3-dithianes to their parent carbonyl compounds via their corresponding monosulfoxides was systemati- cally investigated. The oxidation of the 1,3-dithianes was carried out in high yields using tert-butyl hydroperoxide. Acid-catalyzed hydrolysis of the monosulfoxides to the carbonyl compounds was then performed in excellent yields. The cleavage reactions were monitored by gas chromatography

  系统地研究了 1,3-二噻吩通过其相应的单亚砜水解为其母体羰基化合物。使用叔丁基氢过氧化物以高产率进行 1,3-二噻吩的氧化。然后以优异的产率将单亚砜酸催化水解成羰基化合物。通过气相色谱监测裂解反应，并在电子密度和空间要求不同的底物上研究动力学。这两种效应都不会阻止裂解反应的高总产率。
• 2,6-Dicarboxypyridinium Chlorochromate. An Efficient and Selective Reagent for the Mild Deprotection of Acetals, Thioacetals, and 1,1-Diacetates to Carbonyl Compounds
  作者：Rahman Hosseinzadeh、Mahmood Tajbakhsh、Alireza Shakoori、Mohammad Yazdani Niaki

  DOI：10.1007/s00706-004-0193-7

  日期：2004.10

  chlorochromate (2,6- DCPCC ) was found to be an efficient reagent for the conversion of acetals, thioacetals, and 1,1-diacetates to their corresponding carbonyl compounds under neutral and anhydrous conditions in good to excellent yields. Selective deprotection of acetals or 1,1-diacetates in the presence of thioacetals at room temperature is also observed with this reagent.

  发现2,6-二 羧基吡啶鎓氯铬酸盐（2,6- DCPCC ）是一种在中性和无水条件下以良好或优异的收率将乙缩醛，硫缩醛和1,1-二乙酸酯转化为相应的羰基化合物的有效试剂。用该试剂在室温下也观察到在乙缩醛存在下乙缩醛或1，1-二乙酸酯的选择性脱保护。
• 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。
• The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
  作者：Qun Liu、Guangbo Che、Haifeng Yu、Yingchun Liu、Jingping Zhang、Qian Zhang、Dewen Dong

  DOI：10.1021/jo034702t

  日期：2003.11.1

  equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.

  使用Vilsmeier-Haack通过氯化3-（1,3）-二硫代亚戊基戊烷-2,4-二酮2来合成2- [2-氯-1-（1-氯乙烯基）亚芳基] -1,3-二硫代烷1。试剂产率为99％。在硫代缩醛化反应中，研究了一种新型的无硫，无味的1,3-丙二硫醇当量。在1的存在下，各种类型的醛和酮3以高收率（79-97％）转化为相应的二噻烷4。此外，在该硫代缩醛化反应中，1在醛和酮之间表现出明显的化学选择性。提出了该硫缩醛化反应的机理。