(dodec-1-yl-trisulfanyl)benzene | 1262447-21-1

• 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: (dodec-1-yl-trisulfanyl)benzene
• 英文别名: 1-dodecyl-3-phenyltrisulfane；(Dodecyltrisulfanyl)benzene
• CAS: 1262447-21-1
• 化学式: C₁₈H₃₀S₃
• 分子量: 342.634
• InChiKey: XKZJVCFJGRLZME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-dodecyl 4-methylbenzenesulfonothioate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.18h， 生成 (dodec-1-yl-trisulfanyl)benzene
  参考文献：
  名称：

  Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate

  摘要：

  New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 degrees C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.

  DOI：

  10.1021/acs.joc.8b03262

文献信息

• Efficient Synthesis of Functionalized Unsymmetrical Dialkyl Trisulfanes
  作者：Dariusz Witt、Slawomir Lach

  DOI：10.1055/s-0033-1338966

  日期：——

  We have developed a convenient method for the synthesis of functionalized unsymmetrical dialkyl trisulfanes under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with alkyl disulfanyl anions generated in situ from S-acetyl disulfanyl derivatives and sodium methoxide. The developed method

  我们开发了一种方便的方法，可以在温和的条件下以非常好的收率合成功能化的不对称二烷基三硫烷。所设计的方法基于 (5,5-二甲基-2-硫代-1,3,2-二氧杂膦基-2-基)-二硫烷基衍生物与 S-乙酰二硫烷基衍生物和钠原位生成的烷基二硫烷基阴离子的反应。甲醇。所开发的方法允许制备在三硫烷官能团两侧带有额外羟基、羧基或氨基官能团的不对称三硫烷。
• Novel and Efficient Synthesis of Unsymmetrical Trisulfides
  作者：Dariusz Witt、Slawomir Lach、Magdalena Sliwka-Kaszynska

  DOI：10.1055/s-0030-1259033

  日期：2010.12

  We have developed a convenient method for the synthesis of unsymmetricaltrisulfides under mild conditions in very good yields. The designedmethod is based on the straightforward preparation of 1-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecanefrom readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane,sulfur dichloride (SCl 2 ) and dodecane-1-thiol. The

  我们开发了一种在温和条件下以非常好的产率合成不对称三硫化物的简便方法。设计的方法基于从容易获得的 5,5-二甲基-2-硫烷基中直接制备 1-[(5,5-二甲基-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)trisulfanyl]dodecane- 2-thioxo-1,3,2-dioxaphosphorinane、二氯化硫 (SCl 2 ) 和十二烷-1-硫醇。不对称三硫化物也可以从脂肪族、芳香族硫醇和 L-半胱氨酸衍生物中获得。