1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol | 701935-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol
• 英文别名: 1-(4-methylsulfonylphenyl)-2-propen-1-ol；1-(4-Methanesulfonylphenyl)prop-2-en-1-ol；1-(4-methylsulfonylphenyl)prop-2-en-1-ol
• CAS: 701935-65-1
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: NKGKSQYGRPVLOT-UHFFFAOYSA-N

物化性质

• 熔点：
  56.5-57.5 °C
• 沸点：
  400.8±37.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol 在 4 A molecular sieve 、 N,N-二异丙基乙胺 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium hydroxide 、 potassium osmate(VI) 、 L-(+)-diisopropyl tartrate 、 次氯酸叔丁酯 作用下， 以 甲醇 、 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 甲砜霉素
  参考文献：
  名称：

  使用束缚的氨基羟化反应短时对映体合成（-）-氯霉素和（+）-噻吩酚

  摘要：

  描述了一种有效的对映选择性合成（-）-氯霉素（1）和（+）-噻吩酚（2）。这些抗生素已分别通过束缚的氨基羟基化和Sharpless不对称环氧化作为手性诱导步骤，分别由市售的4-硝基苯甲醛和4-（甲硫基）苯甲醛合成。

  DOI：

  10.1016/j.tet.2006.08.019
• 作为产物：
  描述：

  1-[4-(甲基硫烷基)苯基]-2-丙烯-1-醇 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以95%的产率得到1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol
  参考文献：
  名称：

  使用束缚的氨基羟化反应短时对映体合成（-）-氯霉素和（+）-噻吩酚

  摘要：

  描述了一种有效的对映选择性合成（-）-氯霉素（1）和（+）-噻吩酚（2）。这些抗生素已分别通过束缚的氨基羟基化和Sharpless不对称环氧化作为手性诱导步骤，分别由市售的4-硝基苯甲醛和4-（甲硫基）苯甲醛合成。

  DOI：

  10.1016/j.tet.2006.08.019

文献信息

• Palladium-Catalyzed Oxidative Nonclassical Heck Reaction of Arylhydrazines with Allylic Alcohols via C–N Bond Cleavage: Access to β-Arylated Carbonyl Compounds
  作者：Xiaoshuo Wang、Xiaojing Wang、Hongwu Pan、Xiayi Ming、Zhenming Zhang、Tao Wang

  DOI：10.1021/acs.joc.2c01115

  日期：2022.8.5

  An efficient palladium-catalyzed oxidative nonclassical Heck reaction of arylhydrazines with allylic alcohols via C–N bond cleavage has been successfully developed. This method provides a series of β-arylated carbonyl compounds with broad functional group tolerance under base-free, simple, and mild open air reaction conditions. In the reaction, arylhydrazines with the smaller molecular weight of the

  已经成功地开发了一种有效的钯催化的芳基肼与烯丙醇通过 C-N 键断裂的氧化非经典 Heck 反应。该方法在无碱、简单和温和的露天反应条件下提供了一系列具有广泛官能团耐受性的β-芳基化羰基化合物。在该反应中，离去基团分子量较小的芳基肼被用作“绿色”芳基化试剂，在空气中释放出副产物N 2和水。机理研究表明，涉及芳基自由基过程和 Pd-H 复合迁移重新插入。此外，抗心律失常药物普罗帕酮的合成以该转化为关键步骤完成。
• Copper/Ruthenium Relay Catalysis for Stereodivergent Access to δ‐Hydroxy α‐Amino Acids and Small Peptides
  作者：Cong Fu、Ling He、Xin Chang、Xiang Cheng、Zuo‐Fei Wang、Zongpeng Zhang、Vladimir A. Larionov、Xiu‐Qin Dong、Chun‐Jiang Wang

  DOI：10.1002/anie.202315325

  日期：2024.2.12

  An atom- and step-economical and redox-neutral cascade reaction enabled by dual-metal relay catalysis by merging borrowing-hydrogen and Michael addition reactions provided access to all stereoisomers of 2-amino-5-hydroxyvaleric acid derivatives with 1,4-non-adjacent stereocenters. Concise stereodivergent synthesis of key intermediates for the synthesis of biologically important chiral molecules further

  通过合并借氢和迈克尔加成反应，通过双金属接力催化实现原子和步骤经济且氧化还原中性的级联反应，提供了获得 2-氨基-5-羟基戊酸衍生物与 1,4-non 的所有立体异构体的途径-相邻的立体中心。用于合成生物学上重要的手性分子的关键中间体的简洁立体发散合成进一步展示了该方法的合成效用。
• A short stereoselective synthesis of (−)-chloramphenicol and (+)-thiamphenicol
  作者：G. Bhaskar、V. Satish Kumar、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2004.03.007

  日期：2004.4

  A common strategy for the synthesis of (-)-chloramphenicol and (+)-thiamphenicol is described. These antibiotics have been synthesized from commercially available 4-nitrobenzaldehyde and 4-(methylthio)benzaldehyde in three and four steps, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
• New inhibitors of colony spreading in Bacillus subtilis and Bacillus anthracis
  作者：Xin Hao、Tam Nguyen、Daniel B. Kearns、Carolynn C. Arpin、Ray Fall、Tarek Sammakia

  DOI：10.1016/j.bmcl.2011.06.082

  日期：2011.9

  We have recently characterized sliding motility in Bacillus subtilis strains that lack functional flagella, and here describe the discovery of inhibitors of colony spreading in these strains as well as the aflagellate pathogen, Bacillus anthracis. Aflagellate B. subtilis strains were used to screen for new types of antibacterials that might inhibit colony spreading on semi-solid media. From a diverse set of organic structures, p-nitrophenylglycerol (NPG), an agent used primarily in clinical laboratories to control Proteus swarming, was found to inhibit colony spreading. The four stereoisomers of NPG were synthesized and tested, and only the 1R,2S-(1R-anti) and 1R,2R-(1R-syn) NPG isomers had significant activity in a quantitative colony spreading assay. Twenty-six NPG analogs and related structures were synthesized and tested to identify more active inhibitors. p-Methylsulfonylphenylglycerol (p-SPG), but not its ortho or meta analogs, was found to be the most effective of these compounds, and synthesis and testing of all four p-SPG stereoisomers showed that the 1R-anti-isomer was the most active with an average IC50 of 16 mu M (3-5 mu g mL (1)). For B. anthracis, the colony-spreading IC50 values for 1R-anti-SPG and 1R-anti-NPG are 12 mu M (2-4 mu g mL (1)) and >150 mu M, respectively. For both Bacillus species tested, 1R-anti-SPG inhibits colony spreading of surface cultures on agar plates, but is not bacteriostatic or bacteriocidal in liquid cultures. Work is in progress to find the cellular target(s) of the NPG/SPG class of compounds, since this could lead to an understanding of the mechanism(s) of colony spreading as well as design and development of more potent inhibitors for the control of B. anthracis surface cultures. (C) 2011 Elsevier Ltd. All rights reserved.