n-Butyl tert-butyl disulfide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 有机二硫化物
• 英文名称: n-Butyl tert-butyl disulfide
• 英文别名: 1-tert-butyl-2-butyldisulfane；2,2-Dimethyl-3,4-dithiaoctane；1-(tert-butyldisulfanyl)butane
• 化学式: C₈H₁₈S₂
• 分子量: 178.363
• InChiKey: ZCQXAHUBBUBMMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  n-Butyl tert-butyl disulfide 在 氢气 作用下， 以 丙酮 为溶剂， -78.0 ℃ 、399.97 Pa 条件下， 反应 0.02h， 生成 叔丁基二硫 、 丁硫醇 、 二丁基二硫 、 叔丁基硫醇
  参考文献：
  名称：

  The Regioselective Reaction of Atomic Hydrogen with Unsymmetric Disulfides and Sulfides

  摘要：

  Unsymmetric disulfides undergo solution phase reduction with atomic hydrogen regioselectively by displacement at the least hindered sulfur atom. The cleavage of the sulfur-sulfur bond forms mixtures of two thiol and two thiyl radicals. At the temperature at which the reactions are carried out, the thiyl radicals form symmetric disulfides by thiyl-thiyl radical coupling and not by thiyl radical displacement on the starting material. The reaction of atomic hydrogen with an unsymmetric sulfide is a cleavage that favors the formation of the most stable radical. The reaction of phenyl cyclohexyl sulfide produces benzene, cyclohexane, cyclohexyl thiol, and thiophenol. Benzene and cyclohexyl thiol produced from the cleavage of the phenyl-sulfur bond are proposed to arise from the ct-scission of an intermediate formed by ipso-addition of atomic hydrogen to the benzene ring.

  DOI：

  10.1021/jo00119a027
• 作为产物：
  描述：

  丁硫醇 、 叔丁基硫醇 在 三氯异氰尿酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.08h， 以55.6%的产率得到n-Butyl tert-butyl disulfide
  参考文献：
  名称：

  利用TCCA有效地一锅构建不对称二硫键

  摘要：

  我们在这里报告了不对称二硫化物的一锅法合成，其中三氯异氰尿酸（TCCA）为氧化剂。在方便的条件下，即使没有碱，也能以良好至极好的收率合成芳族-芳族二硫化物和芳族-脂族二硫化物。为了构建具有挑战性的脂族-脂肪族二硫化物，还可以在条件略微改变的情况下获得所需产物的良好收率。此外，反应证明了广泛的底物范围，非常短的反应时间（<5分钟）和简便的程序。

  DOI：

  10.1016/j.tetlet.2016.12.007

文献信息

• Efficient one-pot construction of unsymmetrical disulfide bonds with TCCA
  作者：Feng Yang、Wen Wang、Kaidi Li、Weili Zhao、Xiaochun Dong

  DOI：10.1016/j.tetlet.2016.12.007

  日期：2017.1

  We report herein a one-pot synthesis of unsymmetrical disulfides with trichloroisocyanuric acid (TCCA) as an oxidant. Under facile conditions, aromatic-aromatic disulfides and aromatic-aliphatic disulfides were synthesized in good to excellent yields even without base. For the construction of the challenging aliphatic-aliphatic disulfides, good yields of the desired products were also obtained with

  我们在这里报告了不对称二硫化物的一锅法合成，其中三氯异氰尿酸（TCCA）为氧化剂。在方便的条件下，即使没有碱，也能以良好至极好的收率合成芳族-芳族二硫化物和芳族-脂族二硫化物。为了构建具有挑战性的脂族-脂肪族二硫化物，还可以在条件略微改变的情况下获得所需产物的良好收率。此外，反应证明了广泛的底物范围，非常短的反应时间（<5分钟）和简便的程序。
• Beckwith, Athelstan L. J.; Duggan, Sandhya A. M., Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1509 - 1518
  作者：Beckwith, Athelstan L. J.、Duggan, Sandhya A. M.

  DOI：——

  日期：——
• The Regioselective Reaction of Atomic Hydrogen with Unsymmetric Disulfides and Sulfides
  作者：Dennis D. Tanner、Liying Zhang、Markandu Vigneswaran、Pramod Kandanarachchi

  DOI：10.1021/jo00119a027

  日期：1995.7

  Unsymmetric disulfides undergo solution phase reduction with atomic hydrogen regioselectively by displacement at the least hindered sulfur atom. The cleavage of the sulfur-sulfur bond forms mixtures of two thiol and two thiyl radicals. At the temperature at which the reactions are carried out, the thiyl radicals form symmetric disulfides by thiyl-thiyl radical coupling and not by thiyl radical displacement on the starting material. The reaction of atomic hydrogen with an unsymmetric sulfide is a cleavage that favors the formation of the most stable radical. The reaction of phenyl cyclohexyl sulfide produces benzene, cyclohexane, cyclohexyl thiol, and thiophenol. Benzene and cyclohexyl thiol produced from the cleavage of the phenyl-sulfur bond are proposed to arise from the ct-scission of an intermediate formed by ipso-addition of atomic hydrogen to the benzene ring.
• Ground solid permanganate oxidative coupling of thiols into symmetrical/unsymmetrical disulfides: selective and improved process
  作者：Ngan-Giang Thi Nguyen、Xuan-Triet Nguyen、Ngoc-Huy Nguyen、Thi Xuan Thi Luu、Xuan-Tien Dao

  DOI：10.1080/17415993.2022.2083914

  日期：2022.11.2

  The oxidation of thiols to the symmetrical disulfides by using ground solid potassium permanganate under mild and solvent-free conditions has allowed us to selectively oxidize thiols in the presence of other readily oxidized functional groups such as alcohol, aldehyde, amine and alkene without the risk of producing undesired products via competitive oxidation reactions. Unsymmetrical disulfides have

  通过在温和和无溶剂条件下使用研磨的固体高锰酸钾将硫醇氧化为对称二硫化物，我们可以在其他容易氧化的官能团（如醇、醛、胺和烯烃）存在下选择性地氧化硫醇，而不会产生通过竞争性氧化反应产生不需要的产品。通过混合硫醇的氧化偶联，也以中等至良好的产率获得了不对称二硫化物。此外，在空间要求高的烷硫醇或芳硫醇氧化的情况下，与常规搅拌相比，超声或微波辐照能够缩短反应时间。