2-(2-hydroxy-ethylsulfanylmethyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-hydroxy-ethylsulfanylmethyl)phenol
• 英文别名: 1-(2-hydroxyphenyl)-1-S-(2-hydroxyethylthio)methane；1-S-(2-hydroxyethylthio)-1-(2-hydroxyphenyl)methane；2-(2-Hydroxyethylsulfanylmethyl)phenol
• 化学式: C₉H₁₂O₂S
• 分子量: 184.259
• InChiKey: AICIPVUTPNXDPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-methylene-cyclohexa-2,4-dienone 、 2-巯基乙醇 以 phosphate buffer 为溶剂， 生成 2-(2-hydroxy-ethylsulfanylmethyl)phenol
  参考文献：
  名称：

  醌甲基化物上的取代基强烈调节其亲核加合物的形成和稳定性

  摘要：

  醌甲基化物 (QM) 的电子扰动极大地影响了它们的稳定性，进而改变了 QM 与脱氧核苷反应的动力学和产物分布。与这种反应性中间体的缺电子性质一致，给电子取代基是稳定的，而吸电子取代基是不稳定的。例如，dC N3-QM 加合物在观察过程中（7 天）通过抑制 QM 再生的吸电子酯基团的存在而变得稳定。相反，具有供电子甲基的相关加合物非常不稳定，并以大约 5 小时的半衰期再生其 QM。这些效应的普遍性通过一系列替代的醌甲基化物前体 (QMP) 得到证明，这些前体含有各种取代基，这些取代基连接在环外亚甲基的不同位置。通过激光闪光光解测量的取代 QM 的亲核加成速率同样跨越 5 个数量级，富电子物种反应最慢，缺电子物种反应最快。QM 反应的可逆性现在可以针对任何所需的应用进行可预测的调整。

  DOI：

  10.1021/ja062948k

文献信息

• Alkylation of Amino Acids and Glutathione in Water by <i>o</i>-Quinone Methide. Reactivity and Selectivity
  作者：Emilia Modica、Riccardo Zanaletti、Mauro Freccero、Mariella Mella

  DOI：10.1021/jo0006627

  日期：2001.1.1

  o-Quinone methide (1) has been produced in water both thermally and photochemically from (2-hydroxybenzyl)trimethylammonium iodide (2). Michael addition reactions of 1 to various amines, and sulfides, including amino acids and glutathione have been carried out, obtaining alkylated adducts (3-16) in fairly good to quantitative yields. The reaction rate and selectivity of 1 toward nitrogen and sulfur

  由（2-羟基苄基）三甲基碘化碘（2）在水中通过热化学和光化学方法制得邻醌甲基化物（1）。已经进行了1对各种胺和硫化物（包括氨基酸和谷胱甘肽）的迈克尔加成反应，以相当好的定量收率获得了烷基化的加合物（3-16）。通过激光闪光光解技术研究了在不同pH条件下1与氮和硫亲核试剂的反应速率和选择性，与水合反应竞争。从水（kNu = 5.8 M-1 s-1）到最具活性的亲核试剂（2.8 x 10（8）M-1 s-1，2-巯基乙醇在碱性条件下）传递时，观察到的反应性跨越7个数量级。这些是亲核加成母体邻苯醌甲基化物（1）的首次直接反应速率测量。竞争实验为游离1作为中间体参与热和光化学反应提供了强大的动力学支持。此外，通过加热（9、10、13和14）或通过辐射（9、11-13、16），几种烷基化加合物可再生1。烷基化过程的这种热和光化学可逆性为诸如o-QM分子载体之类的加合物的使用和应用开辟了新的前景。
• Latent mercaptans as multi-functional additives for halogen-containing polymer compositions
  申请人：Morton International, Inc.

  公开号：US06326518B1

  公开（公告）日：2001-12-04

  Halogen-containing polymer compositions comprising a latent mercaptan-containing heat stabilizer composition substantially free from the offensive odor typically associated with mercaptans are protected during processing by the degradation products of the latent (i.e., blocked) mercaptan which include a free mercaptan. Other products of the degradation are believed to include carbocations of the blocking moiety which are stabilized by a molecular structure in which the electron deficiency is shared by several groups. The latent mercaptan may be the sole heat stabilizer additive but the free mercaptan released during processing may also synergize the activity of metal-based heat stabilizers such as metal salts and organometallic stabilizers such as organotin carboxylates and mercaptides in the polymer composition. The odor of primary mercaptan-containing heat stabilizers in halogenated polymer compositions is masked by a small amount of a latent mercaptan. The latent mercaptans also serve as intermediates in the preparation of anti-oxidants, anti-microbial agents, photostabilizers, and primary heat stabilizers. Highly effective heat stabilizers are prepared by the condensation of formaldehyde and a para-phenol and further condensation of the crude product with a mercapto-containing compound.

  含卤素聚合物组合物包括一种潜在的巯基含量热稳定剂组合物，该组合物基本上不含有通常与巯基相关的刺激性气味，通过潜在（即被阻断的）巯基的降解产物，包括一个自由的巯基，在处理过程中受到保护。降解的其他产物被认为包括阻断部分的碳正离子，其中的电子亏损由几个基团共享的分子结构稳定。潜在的巯基可以是唯一的热稳定剂添加剂，但在处理过程中释放的自由巯基也可以协同金属基热稳定剂（如金属盐）和有机金属稳定剂（如有机锡羧酸盐和巯基化合物）在聚合物组合物中的活性。小量的潜在巯基掩盖了卤代聚合物组合物中含有的主要巯基热稳定剂的气味。潜在巯基还可作为抗氧化剂、抗微生物剂、光稳定剂和主要热稳定剂的制备中间体。通过甲醛和对苯酚的缩聚，并进一步与含巯基的化合物缩聚，可以制备高效的热稳定剂。
• LATENT MERCAPTANS AS MULTI-FUNCTIONAL ADDITIVES FOR HALOGEN-CONTAINING POLYMER COMPOSITIONS
  申请人：——

  公开号：US20020068780A1

  公开（公告）日：2002-06-06

  Halogen-containing polymer compositions comprising a latent mercaptan-containing heat stabilizer composition substantially free from the offensive odor typically associated with mercaptans are protected during processing by the degradation products of the latent (i.e., blocked) mercaptan which include a free mercaptan. Other products of the degradation are believed to include carbocations of the blocking moiety which are stabilized by a molecular structure in which the electron deficiency is shared by several groups. The latent mercaptan may be the sole heat stabilizer additive but the free mercaptan released during processing may also synergize the activity of metal-based heat stabilizers such as metal salts and organometallic stabilizers such as organotin carboxylates and mercaptides in the polymer composition. The odor of primary mercaptan-containing heat stabilizers in halogenated polymer compositions is masked by a small amount of a latent mercaptan. The latent mercaptans also serve as intermediates in the preparation of anti-oxidants, anti-microbial agents, photostabilizers, and primary heat stabilizers. Highly effective heat stabilizers are prepared by the condensation of formaldehyde and a para-phenol and further condensation of the crude product with a mercapto-containing compound.

  含卤素的聚合物组合物包括一种潜在的巯基含量热稳定剂组合物，该组合物基本上不含通常与巯基相关的刺激性气味，通过潜在（即阻塞）巯基的降解产物，包括自由巯基，来保护加工过程中的聚合物组合物。降解的其他产物被认为包括阻塞基的碳正离子，其由多个基团共享电子亏损的分子结构稳定。潜在巯基可以是唯一的热稳定剂添加剂，但在加工过程中释放的自由巯基也可以协同金属基热稳定剂（如金属盐）和有机金属稳定剂（如有机锡羧酸盐和巯基化合物）的活性。在卤化聚合物组合物中，主要巯基含量热稳定剂的气味被少量潜在巯基掩盖。潜在巯基还可用作抗氧化剂、抗微生物剂、光稳定剂和主要热稳定剂的制备中间体。通过甲醛和对苯酚的缩聚，并将粗品与含巯基化合物进一步缩聚，制备出高效的热稳定剂。
• Latent mercaptan stabilizers for improved weatherability of clear halogen-containing polymer compositions
  申请人：MORTON INTERNATIONAL, INC.

  公开号：EP1004624A1

  公开（公告）日：2000-05-31

  Stabilizer compositions useful for protecting clear polyvinyl chloride and other clear halogen-containing polymer compositions used in the manufacture of exterior weatherable products against discoloration and degradation caused by exposure to ultraviolet light and weathering in addition to heat comprising a latent mercaptan which degrades during processing of the composition at an elevated temperature to liberate a free mercaptan, in combination with a synergistic amount of a free phenyl salicylate compound. The latent mercaptan may be the sole heat stabilizer additive in the stabilizer composition, but the free mercaptan released during processing may also synergize the activity of organic-based or metal-based heat stabilizers such as metal salts and organometallic stabilizers such as organotin carboxylates and organotin mercaptides in the polymer composition. Clear polyvinyl chloride and other clear halogen-containing polymer compositions containing these compounds are also provided which exhibit improved ultraviolet light stability and weatherability without detracting from their thermal performance.

  用于保护透明聚氯乙烯和其他透明含卤聚合物组合物的稳定剂组合物，这些组合物可用于制造室外耐候产品，防止因暴露于紫外线和风化以及热量而引起的褪色和降解，该组合物包括一种潜硫醇，在组合物加工过程中，该潜硫醇在高温下降解，释放出游离硫醇，并与一定量的游离水杨酸苯化合物协同作用。潜硫醇可以是稳定剂组合物中唯一的热稳定剂添加剂，但在加工过程中释放的游离硫醇也可以协同聚合物组合物中的有机基或金属基热稳定剂（如金属盐和有机金属稳定剂（如有机锡羧酸盐和有机锡硫醇盐））的活性。 此外，还提供了含有这些化合物的透明聚氯乙烯和其他透明含卤聚合物组合物，它们具有更好的紫外线稳定性和耐候性，而不会影响其热学性能。
• A halogen-containing polymer composition stabilized by a latent mercaptan and a mixture of a zinc carboxylate and zinc chloride
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1201706A1

  公开（公告）日：2002-05-02

  Flexible, semi-rigid, and rigid vinyl chloride polymer compositions containing a heat stabilizer comprising a latent mercaptan and a mixture of zinc chloride and a zinc carboxylate are substantially free from the offensive odor typically associated with mercaptans and are protected during processing by the degradation products of the latent (i.e., blocked) mercaptan which include a free mercaptan. The free mercaptan thus released enhances the activity of the mixture of zinc chloride and zinc carboxylate.

  软质、半硬质和硬质氯乙烯聚合物组合物含有一种热稳定剂，该热稳定剂包括一种潜伏硫醇以及氯化锌和羧酸锌的混合物，基本上没有通常与硫醇有关的刺激性气味，并且在加工过程中受到潜伏硫醇（即封存硫醇）降解产物（包括游离硫醇）的保护。游离硫醇的释放增强了氯化锌和羧酸锌混合物的活性。