dodecyl triphenylmethyl sulfide | 145544-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: dodecyl triphenylmethyl sulfide
• 英文别名: 12-(S-trityl)mercaptododecane；1-dodecyl trityl sulfide；1-(Triphenylmethylthio)dodecane；[dodecylsulfanyl(diphenyl)methyl]benzene
• CAS: 145544-33-8
• 化学式: C₃₁H₄₀S
• 分子量: 444.725
• InChiKey: BVDANPKCANPNCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dodecyl triphenylmethyl sulfide 在 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 二氯甲烷 为溶剂， 以61 %的产率得到二月桂基二硫醚
  参考文献：
  名称：

  三苯甲基保护的硫醇和醇的光催化裂解

  摘要：

  我们报告了在 pH 中性条件下三苯甲基硫醚或醚的可见光光催化裂解。该方法导致以中等到极好的收率形成相应的对称二硫化物和醇。该协议只需要添加合适的光催化剂和光使其与多种功能正交，包括酸不稳定保护基团。相同的条件可用于直接将三苯甲基保护的硫醇转化为不对称的二硫化物或硒硫化物，并在固相有机合成中裂解三苯甲基树脂。

  DOI：

  10.1055/a-1979-5933
• 作为产物：
  描述：

  三苯基甲醇 、 十二硫醇 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以100%的产率得到dodecyl triphenylmethyl sulfide
  参考文献：
  名称：

  使用基于三苯甲基的三氟甲磺酸Y催化剂的基于三苯甲基的多合一试剂，由邻甲硅烷基辅助的三氟甲基芳烃的单个CF键的功能化。

  摘要：

  三氟甲基芳烃的单个CF键的催化巯基化和叠氮反应是通过邻甲硅烷基和多合一试剂协助生成的三苯甲基阳离子和亲核试剂。由于温和的条件而没有产生布朗斯台德酸，由三氟甲磺酸催化的反应有效地提供了各种各样的二氟亚甲基，避免了进一步的CF键裂解。

  DOI：

  10.1002/chem.202001315

文献信息

• Dehydration Reactions in Water. Surfactant-type Brønsted Acid-catalyzed Dehydrative Etherification, Thioetherification, and Dithioacetalization in Water
  作者：Shu Kobayashi、Shinya Iimura、Kei Manabe

  DOI：10.1246/cl.2002.10

  日期：2002.1

  Dehydration reactions such as etherification, thioetherification, and dithioacetalization are efficiently catalyzed by a surfactant-type Bronsted acid in water.

  醚化、硫醚化和二硫代缩醛等脱水反应在水中由表面活性剂型布朗斯台德酸有效催化。
• Dehydration Reactions in Water. Brønsted Acid−Surfactant-Combined Catalyst for Ester, Ether, Thioether, and Dithioacetal Formation in Water
  作者：Kei Manabe、Shinya Iimura、Xiang-Min Sun、Shū Kobayashi

  DOI：10.1021/ja026241j

  日期：2002.10.1

  Dehydration reactions in water have been realized by a surfactant-type catalyst, dodecylbenzenesulfonic acid (DBSA). These reactions include dehydrative esterification, etherification, thioetherification, and dithioacetalization. In these reactions, DBSA and substrates form emulsion droplets whose interior is hydrophobic enough to exclude water molecules generated during the reactions. Detailed studies on the esterification revealed that the yields of esters were affected by temperature, amounts of DBSA used, and the substrates. Esters were obtained in high yields for highly hydrophobic substrates. On the basis of the difference in hydrophobicity of the substrates, unique selective esterification and etherification in water were attained. Furthermore, chemospecific, three-component reactions under DBSA-catalyzed conditions were also found to proceed smoothly. This work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.
• Hydrophobic Polymer-Supported Catalyst for Organic Reactions in Water:  Acid-Catalyzed Hydrolysis of Thioesters and Transprotection of Thiols
  作者：Shinya Iimura、Kei Manabe、Shū Kobayashi

  DOI：10.1021/ol026906m

  日期：2003.1.1

  A hydrophobic polystyrene-supported sulfonic acid was found to be effective for hydrolysis of thioesters in pure water. It was revealed that the catalyst was much superior to other Bronsted acid catalysts. Transprotection of thiols from thioesters to thioethers has been successfully performed in water using this catalytic system.
• Synthesis of symmetrical and unsymmetrical alkyl disulfides with attached flavin analog for formation of self-assembled monolayers on gold
  作者：Suk-Wah Tam-Chang、James C Mason

  DOI：10.1016/s0040-4020(99)00836-4

  日期：1999.11

  We describe a general procedure for the synthesis of symmetrical and unsymmetrical disulfides with an attached flavin analog. Self-assembled monolayers of these disulfides on gold have potential applications as pH sensors and electrocatalysts, The use of a self-assembled monolayer prepared from one of these disulfides in probing the pH Of solutions is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.