4-甲基苯硫代磺酸 S-己基酯 | 28519-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基苯硫代磺酸 S-己基酯
• 中文别名: 4-甲基苯硫代磺酸S-己基酯
• 英文名称: 4-Methylbenzolthiosulfonsaeure-S-hexylester
• 英文别名: S-hexyl 4-methylbenzenesulfonothioate；hexyl 4'-methylbenzenethiosulfonate；n-Hexyl-p-toluolthiolsulfonat；S-Hexyl p-toluenethiosulfonate；1-hexylsulfanylsulfonyl-4-methylbenzene
• CAS: 28519-32-6
• 化学式: C₁₃H₂₀O₂S₂
• 分子量: 272.433
• InChiKey: YCOCBHPNOONOQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-甲基苯硫代磺酸 S-己基酯 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 hexyl 5,9,13-trimethyl-1(E),4(E),8(E),12-tetradecatraienyl sulfide
  参考文献：
  名称：

  Squalene synthetase inhibitors: synthesis of sulfonium ion mimics of the carbocationic intermediates

  摘要：

  Synthesis of sulfonium ion mimics 15 and 16 of the carbocationic intermediates 3 and 7, respectively, presumed to be involved in the squalene synthetase catalyzed rearrangement of farnesyl pyrophosphate (1), is reported. Synthesis of 15 involved combination of homogeranyl sulfide with with ethyl alpha-bromoacetate through use of the thallium salt or via the combination of the copper enolate of ethyl acetate and homogeranyl thiosulfonate. Alkylation of the resulting thioester with farnesyl bromide followed by reduction of the ester moiety provided the required alcohol. The sulfur was methylated with iodomethane in a solution of CH3CN and THF to yield 15. Dialkylation of acetylene with farnesyl bromide and homogeranyl thiosulfonate followed by reduction of the triple bond gave vinyl sulfides, which were methylated with iodomethane in the presence of silver perchlorate to give 16.

  DOI：

  10.1021/jo00012a016
• 作为产物：
  描述：

  1-己硫醇 、 4-methylbenzenediazonium tetrafluoroborate 在 双(二氧化硫)-1,4-二氮杂双环[2.2.2]辛烷加合物 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 0.5h， 以62%的产率得到4-甲基苯硫代磺酸 S-己基酯
  参考文献：
  名称：

  通过插入二氧化硫的无金属合成硫代磺酸盐

  摘要：

  开发了一种简单且无催化剂的策略，使用容易获得的DABCO⋅（SO 2）2作为固体和稳定的二氧化硫替代物来合成不对称硫代磺酸盐。通过具有良好官能团耐受性的自由基途径获得了相应的硫代磺酸盐。该策略为合成化学和药物化学领域中构建各种有用的硫代磺酸盐提供了一种有前途的合成方法，并扩展了仍然有限的二氧化硫固定策略的数量。

  DOI：

  10.1002/adsc.201900157

文献信息

• Synthesis of (Furyl)Methyl Disulfides via Tandem Reaction of Conjugated Ene-Yne-Ketones with Acetyl-Masked Disulfide Nucleophiles
  作者：Xianhang Zhou、Yuhao Jiang、Jiaxin Li、Jinsong Wang、Jianxin Chen、Yue Yu、Hua Cao

  DOI：10.1021/acs.joc.3c02684

  日期：——

  In this study, we outline a general method for the construction of various (furyl)methyl disulfides from acetyl-masked disulfide nucleophiles and ene-yne-ketones. This protocol is feathered by metal-free, simple experimental conditions, high efficiency, and scalable potential, which make it attractive and practical.

  在这项研究中，我们概述了从乙酰基掩蔽的二硫化物亲核试剂和烯炔酮构建各种（呋喃基）甲基二硫化物的通用方法。该协议具有无金属、实验条件简单、效率高和可扩展潜力等特点，使其具有吸引力和实用性。
• Sulfonyl-Promoted Michaelis–Arbuzov-Type Reaction: An Approach to S/Se–P Bonds
  作者：Suhail A. Rather、Mohammad Yaqoob Bhat、Feroze Hussain、Qazi Naveed Ahmed

  DOI：10.1021/acs.joc.1c01681

  日期：2021.10.1
• Scholz, Dieter, Liebigs Annalen der Chemie, 1984, # 2, p. 259 - 263
  作者：Scholz, Dieter

  DOI：——

  日期：——
• Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate
  作者：Doaa Ali、Roger Hunter、Catherine H. Kaschula、Stephen De Doncker、Sophie C. M. Rees-Jones

  DOI：10.1021/acs.joc.8b03262

  日期：2019.3.1

  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.
• Alkyl and Aryl Thiolsulfonates
  作者：James P. Weidner、Seymour S. Block

  DOI：10.1021/jm00335a028

  日期：1964.9