1-[4-(甲硫基)苯基]-1-丙酮 | 52129-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-(甲硫基)苯基]-1-丙酮
• 中文别名: 6-氯咪唑并[1,2-a]吡啶盐酸
• 英文名称: 1(4-methylthiophenyl)-1-propanone
• 英文别名: 4'-(methylthio)propiophenone；p-methylmercaptopropiophenone；1-(4-(methylthio)phenyl)propan-1-one；4-Methylmercapto-propiophenon；p-Methylthiopropiophenon；1-(4-methylsulfanyl-phenyl)-propan-1-one；1-(4-Methylmercapto-phenyl)-propan-1-on；4-(Methylthio)phenyl-propan-1-one；1-(4-Methylsulfanylphenyl)propan-1-one
• CAS: 52129-99-4
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: FTJGECIARDVRJC-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C
• 沸点：
  184 °C(Press: 20 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-[4-(甲硫基)苯基]-1-丙酮 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 1-[4-(甲基磺酰基)苯基]-1-丙酮
  参考文献：
  名称：

  Methylsulfonyl and Hydroxyl Substituents InduceZ-Stereocontrol in the McMurry Olefination Reaction

  摘要：

  具有甲基磺酰基和羟基取代基的芳基酮，能够引导立体控制，在Zn-TiCl4催化的McMurry反应中选择性地生成Z-烯烃。

  DOI：

  10.1055/s-2004-829087
• 作为产物：
  描述：

  1-[4-(methylthio)phenyl]-1-hydroxypropyl 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-[4-(甲硫基)苯基]-1-丙酮
  参考文献：
  名称：

  Synthesis and serotonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents

  摘要：

  The discovery that some serotonin reuptake transporter (SERT) ligands have the potential to act as pro-apoptotic agents in the treatment of cancer adds greatly to their diverse pharmacological application. 4-Methylthioamphetamine (MTA) is a selective ligand for SERT over other monoamine transporters. In this study, a novel library of structurally diverse 4-MTA analogues were synthesised with or without N-alkyl and/or C-alpha methyl or ethyl groups so that their potential SERT-dependent antiproliferative activity could be assessed.Many of the compounds displayed SERT-binding activity as well as cytotoxic activity. While there was no direct correlation between these two effects, a number of derivatives displayed anti-tumour effects in lymphoma, leukaemia and breast cancer cell lines, showing further potential to be developed as possible chemotherapeutic agents. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.027

文献信息

• Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes
  作者：Peng Lu、Xiang Ren、Haofeng Xu、Dongpo Lu、Yufeng Sun、Zhan Lu

  DOI：10.1021/jacs.1c04773

  日期：2021.8.18

  for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance

  在这里，我们首次报道了铁催化的高度对映选择性氢化的最低限度官能化的 1,1-二取代烯烃，以获得具有完全转化率和优异ee 的手性烷烃。设计并合成了一种新型手性8-恶唑啉亚氨基喹啉配体及其铁配合物。该协议通过使用 1 个大气压的氢气操作简单，并显示出良好的官能团耐受性。氘标记实验提出了一种主要机制。
• Influences of Electronic Effects and Anions on the Enantioselectivity in the Oxazaborolidine-Catalyzed Asymmetric Borane Reduction of Ketones
  作者：Xu、Wei、Zhang

  DOI：10.1021/jo048959i

  日期：2004.10.1

  influence of electronic effects on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been observed and investigated with use of para-substituted acetophenones and propiophenones with a variety of functional groups and B-unsubstituted and B-methoxyoxazaborolidines derived from (S)-2-(diphenylhydroxymethyl)pyrrolidine with borane and trimethyl borate as catalysts

  已经观察到并研究了电子效应对恶唑硼烷催化的不对称硼烷还原酮的对映选择性的影响，并使用了具有各种官能团的对位取代的苯乙酮和丙苯酮，以及衍生自（S的B-未取代的和B-甲氧基恶唑硼烷）-2-（二苯基羟甲基）吡咯烷与硼烷和硼酸三甲酯在甲苯和THF中的催化剂。结果表明，Hammett线性自由能电子对不对称还原中对映选择性的影响得到了观察和合理化。调节催化剂的电子效应可以提高还原反应中的对映选择性。另一个值得注意的发现是，由于阴离子与催化剂中的硼原子配位，因此阴离子对映选择性特别是对B-甲氧基催化剂影响很大。
• Photoredox/nickel-catalyzed hydroacylation of ethylene with aromatic acids
  作者：Lili Zhang、Shuai Chen、Hengchi He、Weipeng Li、Chengjian Zhu、Jin Xie

  DOI：10.1039/d1cc04188f

  日期：——

  We report a general, practical and scalable hydroacylation reaction of ethylene with aromatic carboxylic acids with the synergistic combination of nickel and photoredox catalysis. Under ambient temperature and pressure, feedstock chemicals such as ethylene can be converted into high-value-added aromatic ketones in moderate to good yields (up to 92%) with reaction time of 2–6 hours.

  我们报告了乙烯与芳香族羧酸在镍和光氧化还原催化的协同组合下的通用、实用和可扩展的加氢酰化反应。在环境温度和压力下，原料化学品，如乙烯可在中等至良好的产率（高达92％），用2反应时间被转化成高附加值的芳香族酮- 6小时。
• Rearrangement of <i>N</i>-<i>tert</i>-Butanesulfinyl Enamines for Synthesis of Enantioenriched α-Hydroxy Ketone Derivatives
  作者：Chun-Tian Li、Hui Liu、Yun Yao、Chong-Dao Lu

  DOI：10.1021/acs.orglett.9b03159

  日期：2019.10.18

  hexamethyldisilazide (or potassium tert-butoxide) and methyl triflate gives N-methylated N-tert-butanesulfinyl enamine intermediates that undergo stereoselective [2,3]-rearrangement to afford α-sulfenyloxy ketones with excellent enantiopurities. This cascade of enamination-N-methylation-rearrangement was even used to generate acyclic tertiary α-hydroxy ketones bearing two α-substituents showing negligible

  用六甲基二硅叠氮化钾（或叔丁醇钾）和三氟甲磺酸甲酯处理手性N-叔丁烷亚砜基酮亚胺，可得到N-甲基化的N-叔丁烷亚砜基烯胺中间体，该中间体经立体选择性[2,3]重排可制得具有优异α-亚磺酰氧基酮的化合物对映体。这种级联的N-甲基化重排反应甚至被用于生成带有两个α-取代基的无环叔α-羟基酮，这些α-取代基的体积差异可忽略不计，例如甲基和乙基。
• Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light
  作者：Blaž Grjol、Marjan Jereb

  DOI：10.1007/s11696-021-01711-x

  日期：2021.10

  methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

  摘要在无溶剂反应条件下，研究了可见光诱导的一系列（杂）芳基烷基取代酮与 N-溴代琥珀酰亚胺 (NBS) 的区域选择性转化，这些酮具有多个竞争性反应位点（α-羰基、苄基和芳环）。 (SFRC) 并且在没有惰性气体气氛、自由基引发剂和催化剂的情况下。使用 8 W 节能家用灯进行照射。在整个研究过程中处理了多相反应条件。所有底物在 α-羰基位置均为单溴化或二溴化，此外，在具有苄基碳原子或给电子甲氧基的底物中分别观察到一些苄基或芳族溴化。令人惊讶的是，与（4-甲氧基萘基）烷基酮发生了用溴原子对酰基的原位取代。