2-hydroxy-1,2-bis(4-methylsulfanyl-phenyl)ethanone | 42445-18-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-hydroxy-1,2-bis(4-methylsulfanyl-phenyl)ethanone
• 英文别名: 4,4'-DI(Methylthio)benzoin；2-hydroxy-1,2-bis(4-methylsulfanylphenyl)ethanone
• CAS: 42445-18-1
• 化学式: C₁₆H₁₆O₂S₂
• 分子量: 304.434
• InChiKey: XWGRBLIDRXJFON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1,2-bis(4-methylsulfanyl-phenyl)ethanone 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 37.0h， 生成 4,5-Bis-(4-methanesulfinyl-phenyl)-1,3-dihydro-imidazole-2-thione
  参考文献：
  名称：

  5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents

  摘要：

  A series of substituted 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles were synthesized and evaluated in the rat adjuvant-induced arthritis and mouse oxazolone-induced contact sensitivity assays to determine the potential of these compounds for use as immunoregulatory antiinflammatory agents. This class of compounds was derived by combining salient structural features of the antiinflammatory agent flumizole and the immunoregulatory drug levamisole. Unlike the latter two, a number of compounds in the target series were found to possess the desired combination of activities. Exploration of structure-activity relationships in the adjuvant-induced arthritic rat assay revealed that optimal potency was exhibited by symmetrically substituted 5,6-diaryl compounds having one of the following alkyl heteroatom or halogen functions at the para position: methoxy, ethoxy, methylthio, N-ethyl-N-methylamino, fluoro, or chloro. Scrambling of these two substituent classes to yield the asymmetrically substituted 5,6-diaryl compounds resulted in potent activity only with the 5-alkyl heteroatom, 6-halo-substituted regioisomers. However in the oxazolone-induced contact sensitivity assay, no consistent relationship of variation in activity with structural change was apparent. The initial target compound 5,6-bis(4-methoxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole (1) was compared with its progenitors in additional models of inflammation and immunoregulation.

  DOI：

  10.1021/jm00147a008
• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 在 potassium cyanide 作用下， 以 乙醇 为溶剂， 反应 0.58h， 生成 2-hydroxy-1,2-bis(4-methylsulfanyl-phenyl)ethanone
  参考文献：
  名称：

  α-叠氮基苯乙酮中α裂解与能量转移之间的竞争

  摘要：

  分子建模表明，叠氮化物1b中三重态酮的第一激发态（T 1K）具有（π，π*）构型，其能量比其基态和第二激发态（T 2K）高66 kcal / mol。能量高10 kcal / mol，并具有（n，π*）构型。相比之下，叠氮化物1a的T 1K和T 2K分别以（n，π*）和（π，π*）构型在高于基态74和77 kcal / mol时简并。由于形成了T 1K，叠氮化物1b在甲醇中的激光快速光解（308 nm）产生瞬态吸收（λmax = 450 nm），其衰减速率为2.1×105 s -1形成三重态亚烷基二烯2b（λmax = 320 nm）。测得的腈2b的寿命为16毫秒。相反，叠氮化物1a的激光快速光解（308 nm）由于形成了亚硝基2a（λmax = 320 nm）和苯甲酰基3a（λmax = 370 nm）而产生了瞬态吸收光谱。在甲醇中，3a的衰减为2×10 5 s -1，而亚硝基2a的衰减率为〜91

  DOI：

  10.1021/jo062160k

文献信息

• Base-Promoted Three-Component Cascade Reaction of α-Hydroxy Ketones, Malonodinitrile, and Alcohols: Direct Access to Tetrasubstituted N<i>H</i>-Pyrroles
  作者：Hongjian Liu、Chaorong Qi、Lu Wang、Yanhui Guo、Dan Li、Huanfeng Jiang

  DOI：10.1021/acs.joc.1c00882

  日期：2021.7.16

  malonodinitrile, and alcohols has been developed, providing a direct and efficient route to a range of structurally diverse and synthetically useful 2-alkyloxy-1H-pyrrole-3-carbonitrile derivatives. The reaction involved three different bond (C–C, C–O, and C–N) formations in a single step, and its regioselectivity was depended on the structure of the α-hydroxy ketones employed. The use of easily available

  已经开发了 α-羟基酮、丙二腈和醇的碱促进三组分级联反应，为一系列结构多样且合成有用的 2-烷氧基-1 H-吡咯-3-腈提供了直接有效的途径衍生品。该反应在一个步骤中涉及三种不同的键（C-C、C-O 和 C-N）的形成，其区域选择性取决于所使用的 α-羟基酮的结构。使用容易获得的起始材料、广泛的底物范围、良好的官能团耐受性、操作简单和高原子经济性是新方法的吸引人的特点。
• Nonprostanoid prostacyclin mimetics. 3. Structural variations of the diphenyl heterocycle moiety
  作者：Nicholas A. Meanwell、Michael J. Rosenfeld、Ashok K. Trehan、Jeffrey L. Romine、J. J. Kim Wright、Catherine L. Brassard、John O. Buchanan、Marianne E. Federici、J. Stuart Fleming、Marianne Gamberdella、George B. Zavoico、Steven M. Seiler

  DOI：10.1021/jm00097a007

  日期：1992.9

  4,5-Diphenyl-2-oxazolenonanoic acid (2) and 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetic acid (3) were previously identified as nonprostanoid prostacyclin (PGI2) mimetics that inhibit ADP-induced aggregation of human platelets in vitro. The effects on biological activity of substitution and structural modification of the 4- and 5-phenyl rings of 3 was examined. Potency showed a marked sensitivity

  4,5-二苯基-2-恶唑壬酸（2）和2- [3- [2-（4,5-二苯基-2-恶唑基）乙基]苯氧基]乙酸（3）先前被确定为非前列腺素前列环素（PGI2 ）在体外抑制ADP诱导的人类血小板聚集的模拟物。考察了3的4-和5-苯基环对取代和结构修饰的生物活性的影响。效能显示出对将取代基引入这些芳族环的显着敏感性，并且只有双-4-甲基衍生物9j（IC50 = 0.34 microM）与母体结构3（IC50 = 1.2 microM）相比具有增强的效能。在苯环的邻位或间位取代，被噻吩基或环己基部分取代，或限制在平面菲系统中产生的化合物不是ADP诱导的血小板聚集的有效抑制剂。相比之下，杂环部分的变化表明，SAR的严格性要低得多，并且发现许多5和6元杂环可有效替代2和3的恶唑环。二苯甲基部分可作为4,5-的有效等排体自13aad以来的二苯环杂环化合物显示出与3相似的血小板抑制活性。除了3,4,5-三苯基吡唑衍生物13g以外，与类似取代的3
• 5,6-Phenyl-2,3-dihydroimidazo [2,1-b] thiazoles
  申请人：SmithKline Corporation

  公开号：US04263311A1

  公开（公告）日：1981-04-21

  The compounds are 5,6-phenyl-2,3-dihydroimidazo[2,1-b]thiazoles which have antiarthritic activity. A preferred compound is 5,6-bis(p-anisyl)-2,3-dihydroimidazo[2,1-b]thiazole.

  这些化合物是5,6-苯基-2,3-二氢咪唑[2,1-b]噻唑的衍生物，具有抗关节炎活性。其中一种优选的化合物是5,6-双(对甲氧基苯基)-2,3-二氢咪唑[2,1-b]噻唑。
• 2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents
  作者：Palwinder Singh、Anu Mittal、Satwinderjeet Kaur、Wolfgang Holzer、Subodh Kumar

  DOI：10.1039/b803608j

  日期：——

  2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofuran-3-ols were designed and synthesized by the allylations of benzoins followed by iodocyclization and nucleophilic replacement reactions with ethanthiol. These molecules exhibit IC50 for COX-2 at <10 nM concentration and exhibit average GI50 over all the 59 human tumor cell lines at μM concentration.

  通过安息香类化合物的烯丙基化反应，然后与乙硫醇进行碘代环化和亲核置换反应，设计并合成了 2,3-二芳基-5-乙硫甲基四氢呋喃-3-醇。这些分子对 COX-2 的 IC50 小于 10 nM，对所有 59 种人类肿瘤细胞株的平均 GI50 为 μM。
• Compound, Photopolymerization Initiator Containing Said Compound, and Photosensitive Resin Composition Containing Said Photopolymerization Initiator
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US20200392079A1

  公开（公告）日：2020-12-17

  This compound which has excellent solvent solubility and compatibility with a resin, and which can generate bases and radicals with high efficiency by being irradiated with active energy rays, is represented by formula (1), where, in formula (1), R 1 , R 2 , R 3 , R 5 and R 6 represent a hydroxy group or an alkoxy group; the R 4 's independently represent an organic group containing a thioether bond; R 7 and R 9 independently represent a hydrogen atom or an alkyl group with 1 to 4 carbons; R 8 represents an alkylene group or an arylene group; and X represents an oxygen atom or a sulfur atom. A photopolymerization initiator can include said novel compound; and a photosensitive resin composition can include said photopolymerization initiator, from which a cured product can be obtained that has high sensitivity and no metal corrosion.

  这种化合物具有优异的溶剂溶解性和与树脂的兼容性，可以通过受到活性能量辐射而高效地产生碱基和自由基。该化合物由公式（1）表示，其中在公式（1）中，R1、R2、R3、R5和R6代表羟基或烷氧基；R4分别表示含硫醚键的有机基团；R7和R9分别代表氢原子或1至4个碳的烷基基团；R8代表烷基或芳基；X代表氧原子或硫原子。一种光聚合引发剂可以包括上述新化合物；一种光敏树脂组合物可以包括上述光聚合引发剂，从中可以得到高灵敏度且无金属腐蚀的固化产物。