(S)-1-(4-nitrophenyl)-2-propen-1-ol | 914646-11-0

• 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-nitrophenyl)-2-propen-1-ol
• 英文别名: (1S)-1-(4-nitrophenyl)prop-2-en-1-ol
• CAS: 914646-11-0
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: GZYWUWDTKLRMKY-VIFPVBQESA-N

物化性质

• 熔点：
  48-49 °C
• 沸点：
  328.2±30.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-nitrophenyl)-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 氯霉素
  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-硝基苯基)丙-2-烯-1-醇 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二异丙酯 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 癸烷 为溶剂， 反应 48.5h， 生成 (S)-1-(4-nitrophenyl)-2-propen-1-ol
  参考文献：
  名称：

  New inhibitors of colony spreading in Bacillus subtilis and Bacillus anthracis

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.06.082

文献信息

• Sequential Deoxyfluorination Approach for the Synthesis of Protected α,β,γ-Trifluoro-δ-amino Acids
  作者：Raju Cheerlavancha、Aggie Lawer、Marina Cagnes、Mohan Bhadbhade、Luke Hunter

  DOI：10.1021/ol402756e

  日期：2013.11

  Backbone-homologated amino acids have been synthesized, containing three vicinal fluorine atoms placed stereospecifically along the carbon chain. Different trifluoro stereoisomers are found to have contrasting conformations, consistent with known stereoelectronic effects associated with C–F bonds.

  已经合成了骨架同源氨基酸，其中包含三个沿碳链立体定向放置的邻位氟原子。发现不同的三氟立体异构体具有相反的构象，与与C-F键相关的已知立体电子效应一致。
• Kinetic resolution of allylic alcohols via stereoselective acylation catalyzed by lipase PS-30
  作者：Peiran Chen、Peng Xiang

  DOI：10.1016/j.tetlet.2011.08.093

  日期：2011.11

  By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic allylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 968. Substituent effect is briefly discussed.

  通过使用脂肪酶PS-30作为催化剂，已通过立体选择性酰化反应实现了一系列外消旋烯丙醇的动力学拆分。动力学对映体比率（E）的值达到968。简要讨论了取代基的作用。
• 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.
• A short enantioselective synthesis of (−)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation
  作者：Shyla George、Srinivasarao V. Narina、Arumugam Sudalai

  DOI：10.1016/j.tet.2006.08.019

  日期：2006.10

  An efficient enantioselective synthesis of (−)-chloramphenicol (1) and (+)-thiamphenicol (2) is described. These antibiotics have been synthesized from commercially available 4-nitrobenzaldehyde and 4-(methylthio)benzaldehyde, respectively, using tethered aminohydroxylation and Sharpless asymmetric epoxidation as the chirality inducing steps.

  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。
• 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.