2-(benzo[d]thiazol-2-ylthio)-1-phenylethan-1-ol | 75219-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-ylthio)-1-phenylethan-1-ol
• 英文别名: 2-(1,3-Benzothiazol-2-ylsulfanyl)-1-phenylethanol
• CAS: 75219-18-0
• 化学式: C₁₅H₁₃NOS₂
• 分子量: 287.406
• InChiKey: NGSHPIXLSKIQKW-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  474.4±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-ylthio)-1-phenylethan-1-ol 在 吡啶 、 MMPP 、 甲基磺酰氯 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 1,5-二苯基-1H-1,2,3-噻唑
  参考文献：
  名称：

  A Metal-Free, Aqueous and General Route to 1,5-Disubstituted-1,2,3-triazoles: ‘Reversed Regioisomeric’ 1,3-Dipolar Cycloaddition of Azides and Vinyl Sulfones

  摘要：

  首次报道了一种无金属的基于乙烯基磺酰的1,5-二取代-1,2,3-三唑的合成方法。这些三唑可以通过在水相中加热回流甲基取代的乙烯基磺酰和有机叠氮化合物的混合物，以区域选择性的方式轻易形成。这条强大且实用的路线有潜力用于合成复杂的1,5-二取代-1,2,3-三唑。

  DOI：

  10.1055/s-0030-1260306
• 作为产物：
  描述：

  2-(1,3-苯并噻唑-2-基硫烷基)-1-苯基乙酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以99%的产率得到2-(benzo[d]thiazol-2-ylthio)-1-phenylethan-1-ol
  参考文献：
  名称：

  酯酶敏感的二氧化硫前药受到朱莉娅（Julia）改性的启发

  摘要：

  二氧化硫（SO 2）是一种内生的气态分子，并正在以潜在的气体传输剂形式出现。在本文中，我们描述了第一批酯酶敏感的前药，该药受改性的Julia烯烃作为SO 2供体的启发。

  DOI：

  10.1039/c7cc05392d

文献信息

• Baker's yeast-induced asymmetric reduction of α-ketosulfides: synthesis of optically active 1-(benzothiazol-2-ylsulfanyl)-2-alkanols, 2-alkanols, and thiiranes
  作者：Leonardo Di Nunno、Carlo Franchini、Angelo Nacci、Antonio Scilimati、Maria Stefania Sinicropi

  DOI：10.1016/s0957-4166(99)00199-8

  日期：1999.5

  enantiomeric excess by baker's yeast-induced asymmetric reduction of 1-(benzothiazol-2-ylsulfanyl)-2-alkanones 1. Conversion of 3 into optically active simple 2-alkanols 4 and thiiranes 2 by reductive desulfurization and base treatment, respectively, is also described. The absolute configuration of the new compounds synthesized has been established by chemical correlation and specific rotation comparison.

  1-（苯并噻唑-2-基硫烷基）-2-链烷醇3是通过贝克酵母诱导的1-（苯并噻唑-2-基硫烷基）-2-链烷酮1的不对称还原以非常高的对映体形式制备的。还描述了分别通过还原性脱硫和碱处理将3转化为旋光的简单2-链烷醇4和噻喃2。通过化学相关性和比旋光度比较，已经确定了合成的新化合物的绝对构型。
• Reaction products of mercaptobenzothiazoles, mercaptothiazolines, and mercaptobenzimidazoles with epoxides as lubricant additives
  申请人：Rowland G. Robert

  公开号：US20050037931A1

  公开（公告）日：2005-02-17

  A composition is disclosed that comprises: (A) a lubricant, and (B) at least one compound selected from the group consisting of alcohols of the formulae: wherein Y is N, O, or S; R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, alkaryl, aryl, alkoxy, and alkyl ester; R 5 is selected from the group consisting of hydrogen, alkyl, alkoxy, a carboxy alkyl group of the structure: (CH 2 ) p CO 2 R 9 where: p is from 1 to 18, and R 9 is hydrocarbyl; R 7 is selected from the group consisting of hydrogen, CH 2 OR 11 , alkyl, and alkenyl, wherein: said alkyl and alkenyl groups are optionally substituted with OH, oxirane, or X; R 11 is selected from the group consisting of alkyl of from 1 to 36 carbon atoms, alkaryl of from 6 to about 50 carbon atoms, and aryl, and may contain ether or ester functionalities; X is of the structure: or R 5 and R 7 are fused together to form a ring of 3-10, preferably 5 or 6, carbon atoms, which may be further substituted with alkyl, cycloalkyl, alkenyl, aryl, or alkoxy groups, and may contain ether or ester functionalities, and R 6 and R 8 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkenyl, aryl, and alkoxy.

  揭示了一种包括：（A）润滑剂和（B）选自以下羟基化合物组合的至少一种化合物的组成物：其中Y为N、O或S；R1、R2、R3和R4独立地选自氢、烷基、环烷基、烯烃基、烷基芳基、芳基、烷氧基和烷基酯基组合的群；R5选自氢、烷基、烷氧基、结构为(CH2)pCO2R9的羧基烷基组（其中：p为1至18，R9为烃基）；R7选自氢、CH2OR11、烷基和烯烃基，其中：所述烷基和烯烃基可以选择性地用OH、环氧乙烷或X取代；R11选自由1至36个碳原子的烷基、由6至约50个碳原子的烷基芳基和芳基组成的组合，并且可能含有醚或酯官能团；X的结构为：或R5和R7被融合在一起形成由3-10个、优选5或6个碳原子的环，该环可能进一步用烷基、环烷基、烯烃基、芳基或烷氧基取代，并且可能含有醚或酯官能团，R6和R8独立地选自氢、烷基、环烷基、烯烃基、芳基和烷氧基组合的群。
• Visible-Light-Induced Organophotocatalytic Difunctionallization: Open-Air Hydroxysulfurization of Aryl Alkenes with Aryl Thiols
  作者：Jee Eun Hong、Yeonghun Jung、Dahye Min、Minji Jang、Soomin Kim、Jiyong Park、Yohan Park

  DOI：10.1021/acs.joc.2c00595

  日期：2022.6.3

  situ generated hydroperoxyl radicals from O2 in air react with benzylic radicals, which restrains the reaction between benzylic radicals and the acidic form of thiols in a classical thiol–ene radical reaction. We show that difunctionalization is possible due to the choice of bases, diluted substrate concentrations, increment in catalyst loading, and selection of suitable aryl thiols under aerobic conditions

  在此，我们报道了一种区域选择性可见光诱导的有机光氧化还原催化双官能化方法，以芳基烯烃和芳基硫醇为底物制备 β-羟基硫化物。该反应提供了广泛的芳基烯烃（从简单的苯乙烯到复杂的生物活性化合物）和芳基硫醇（从各种杂芳族硫醇到非杂芳族硫醇）的底物范围（总共 45 个实例，产率高达 88%）。基于结合的实验和计算研究，我们证明了从 O 2原位产生的氢过氧自由基在空气中与苄基自由基反应，从而抑制了经典硫醇-烯自由基反应中苄基自由基与硫醇的酸性形式之间的反应。我们表明，由于碱的选择、稀释的底物浓度、催化剂负载量的增加以及在有氧条件下选择合适的芳基硫醇，双功能化是可能的。考虑到杂芳族硫醇的生物学重要性以及缺乏安装它们的方法，我们的方法提供了一个衍生各种含有芳族元素的 β-羟基硫化物的平台。
• 10.1021/acs.joc.4c00276
  作者：Yu, Enbo、Li, Jun、Wang, Yue、Chen, Ya、Xiao, Fuhong、Deng, Guo-Jun

  DOI：10.1021/acs.joc.4c00276

  日期：——

  A copper-catalyzed three-component coupling reaction of styrene oxide, aryl iodide, and carbon disulfide for the construction of β-hydroxysulfides has been developed. In this process, readily available CS2 was used as the sulfur source to construct C–S bonds for the synthesis of phenyl-β-hydroxysulfides and (benzo[d]thiazol)-β-hydroxysulfides. This process features mild reaction conditions, simple

  开发了用于构建β-羟基硫化物的铜催化氧化苯乙烯、芳基碘和二硫化碳的三组分偶联反应。在此过程中，使用容易获得的CS 2作为硫源来构建C-S键，用于合成苯基-β-羟基硫化物和(苯并[ d ]噻唑)-β-羟基硫化物。该工艺反应条件温和、操作简单、底物范围广（>50例）。
• Thermolysis of β-hydroxysulfides bearing several heteroaromatics
  作者：Nobuhiko Yamada、Masayoshi Mizuochi、Hiroyuki Morita

  DOI：10.1016/j.tet.2007.01.043

  日期：2007.4

  Thermolyses of beta-hydroxysulfides 2, bearing groups, such as 2-benzothiazolyl and 4-(4-methyl)-4H-1,2,4-triazolyI groups, were studied and found to afford the corresponding substituted styrenes 5 and hydroxy heteroaromatics in good yields, respectively. The product distribution change in the course of the thermolysis of 2a was also studied. The olefin products 5a were considered to be formed by the thermal desulfurization of the corresponding thiiranes 4a initially formed via the five-membered spiro intermediate 6a. (c) 2007 Elsevier Ltd. All rights reserved.