anti-1-(4-methylsulfonylphenyl)glycerol | 1335232-87-5

• 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: anti-1-(4-methylsulfonylphenyl)glycerol
• 英文别名: (1R,2S)-1-(4-methylsulfonylphenyl)propane-1,2,3-triol
• CAS: 1335232-87-5
• 化学式: C₁₀H₁₄O₅S
• 分子量: 246.284
• InChiKey: HVXLXQOZGAPITO-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  anti-1-(4-methylsulfonylphenyl)glycerol 、 苯甲醛 在 硫酸 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以0.44 g的产率得到[(4S,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  一种简便高效的氟苯尼考不对称合成

  摘要：

  描述了从可商购的4-甲基硫代苯甲醛开始的氟苯尼考的​​简便有效的对映选择性合成。合成的关键特征包括在Sharpless环氧化条件下，将烯丙基醇中的烯丙基和硫醚基团一步氧化为（2 S，3 S）-环氧化合物，以及将（1 R，2 R）-叠氮化物高效转化为一锅操作中通过脱苄基化和叠氮基部分的还原得到氨基醇。 氟苯尼考-尖锐的不对称环氧化-一锅法-S N 2亲核取代-氟化

  DOI：

  10.1055/s-0031-1289858
• 作为产物：
  描述：

  (1R,2S)-1-(4-methylsulfonylphenyl)-1,3-bis(phenylmethoxy)propan-2-ol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 anti-1-(4-methylsulfonylphenyl)glycerol
  参考文献：
  名称：

  一种简便高效的氟苯尼考不对称合成

  摘要：

  描述了从可商购的4-甲基硫代苯甲醛开始的氟苯尼考的​​简便有效的对映选择性合成。合成的关键特征包括在Sharpless环氧化条件下，将烯丙基醇中的烯丙基和硫醚基团一步氧化为（2 S，3 S）-环氧化合物，以及将（1 R，2 R）-叠氮化物高效转化为一锅操作中通过脱苄基化和叠氮基部分的还原得到氨基醇。 氟苯尼考-尖锐的不对称环氧化-一锅法-S N 2亲核取代-氟化

  DOI：

  10.1055/s-0031-1289858

文献信息

• 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.
• A Facile and Efficient Asymmetric Synthesis of Florfenicol
  作者：Fen-Er Chen、Feng Li、Zhong-Hua Wang、Lei Zhao

  DOI：10.1055/s-0031-1289858

  日期：2011.12

  A facile and efficient enantioselective synthesis of flor­fenicol starting from commercially available 4-methylthiobenzaldehyde is described. Key features of the synthesis include a one-step oxidation of allyl and thioether groups in allylic alcohol to form (2S,3S)-epoxide under Sharpless epoxidation conditions and a highly efficient conversion of (1R,2R)-azide into amino alcohol via debenzylation

  描述了从可商购的4-甲基硫代苯甲醛开始的氟苯尼考的​​简便有效的对映选择性合成。合成的关键特征包括在Sharpless环氧化条件下，将烯丙基醇中的烯丙基和硫醚基团一步氧化为（2 S，3 S）-环氧化合物，以及将（1 R，2 R）-叠氮化物高效转化为一锅操作中通过脱苄基化和叠氮基部分的还原得到氨基醇。 氟苯尼考-尖锐的不对称环氧化-一锅法-S N 2亲核取代-氟化