(S)-1-(4-methylsulfonylphenyl)-2-propen-1-ol | 914646-16-5

• 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: (S)-1-(4-methylsulfonylphenyl)-2-propen-1-ol
• 英文别名: (1S)-1-(4-methylsulfonylphenyl)prop-2-en-1-ol
• CAS: 914646-16-5
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: NKGKSQYGRPVLOT-JTQLQIEISA-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：

  (S)-1-(4-methylsulfonylphenyl)-2-propen-1-ol 在 N,N-二异丙基乙胺 sodium hydroxide 、 potassium osmate(VI) 、 次氯酸叔丁酯 作用下， 以 甲醇 、 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 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：

  4-(甲基巯基)苯甲醛 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 Oxone 、 L-(+)-diisopropyl tartrate 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 26.5h， 生成 (S)-1-(4-methylsulfonylphenyl)-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

• Asymmetric Synthesis of Florfenicol by Dynamic Reductive Kinetic Resolution with Ketoreductases
  作者：Jie Zou、Guowei Ni、Jiawei Tang、Jun Yu、Luobin Jiang、Dianwen Ju、Fuli Zhang、Shaoxin Chen

  DOI：10.1002/ejoc.201800658

  日期：2018.9.30

  Chemoenzymatic synthesis: The preparation of florfenicol features the use of enzymatic dynamic reductive kinetic resolution (DYRKR) to establish the two stereocenters of the cis‐1,2‐amino alcohol intermediate with >99 % ee and a diastereomeric ratio (dr) of 99 %. The treatment of aziridines and cyclic sulfates with Et3N‐3HF was used to introduce the fluorine atom with high regioselectivity.

  化学酶促合成：氟苯尼考的​​制备方法是利用酶促动态还原动力学拆分（DYRKR）来建立顺式1,2-氨基醇中间体的两个立体中心，其ee大于99％  ，非对映体比率（dr）为99％ 。用Et 3 N-3HF处理氮丙啶和环硫酸盐可以高区域选择性地引入氟原子。
• 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.