(S_S*,2R*)-1-<(4-methylphenyl)sulfinyl>propan-2-ol

• 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_S*,2R*)-1-<(4-methylphenyl)sulfinyl>propan-2-ol
• 英文别名: (2S)-1-[(R)-(4-methylphenyl)sulfinyl]propan-2-ol
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: NBKKIONKSZXVKW-TVQRCGJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S_S*,2R*)-1-<(4-methylphenyl)sulfinyl>propan-2-ol 在 4-二甲氨基吡啶 、 zinc(II) iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 (1S*,2R*)-1,2-bis-(tert-butyldimethylsiloxy)-1-<(4-methylphenyl)sulfanyl>propane
  参考文献：
  名称：

  Kita, Yasuyuki; Shibata, Norio; Yoshida, Naoki, Journal of the Chemical Society. Perkin transactions I, 1994, # 22, p. 3335 - 3342

  摘要：

  DOI：
• 作为产物：
  描述：

  (R_S)-1-(p-tolylsulfinyl)-propan-2-ol 生成 (S_S*,2R*)-1-<(4-methylphenyl)sulfinyl>propan-2-ol
  参考文献：
  名称：

  Selective lipase-catalyzed acylation of epimeric α-sulfinyl alcohols: an efficient method of separation

  摘要：

  A facile and efficient separation of mixtures of epimeric cc-sulfinyl alcohols 2:3 can be accomplished by selective lipase-catalyzed acylation with neat vinyl acetate. Pseudomonas cepacia and Candida rugosa lipase showed opposite epimer differentiation in the esterification. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00026-9

文献信息

• Herstellung enantiomerenreiner Sulfoxide aus Milchsäure und 3-Hydroxybuttersäure: Isopropenyl-tolyl-sulfoxid und 2-(Phenylsulfinyl) acrylester
  作者：Richard Breitschuh、Dieter Seebach

  DOI：10.1055/s-1992-26328

  日期：——

  Preparation of Enantiomerically Pure Sulfoxides from Lactic Acid and 3- Hydroxybutyric Acid. Isopropenyl Tolyl Sulfoxide and 2-(Phenylsulfinyl) acrylate The EPC-synthesis of sulfoxides from readily available starting materials ("chiral pool") is demonstrated for the first time. Cyclic and open-chain thioethers derived from lactic and 3-hydroxybutyric acid are oxidized to sulfoxides, and the resulting products isolated in diastereomerically and enantiomerically pure form. Simple, large-scale conversions lead to methyl (S)-2-(phenylsulfinyl)acrylate and to (R)-isopropenyl tolyl sulfoxide from the corresponding (S)-lactate. Oxidation with tert-butyl hydroperoxide of chiral P-tolylthio-substituted propanols and butanols catalyzed by the addition of 1 % bis(2,4-pentadione)oxyvanadium(IV) (VOacac2) is diastereoselective (2:1 to 5.5: 1).

  以乳酸和 3- 羟基丁酸为原料制备对映体纯硫醚。异丙烯基甲苯基亚砜和 2-(苯基亚磺酰基)丙烯酸酯 首次证明了用易获得的起始材料（"手性池"）进行亚砜的 EPC 合成。从乳酸和 3- 羟基丁酸中提取的环状和开链硫醚被氧化成硫醚，并分离出非对映和对映体纯的产物。通过简单、大规模的转化，可以从相应的(S)-乳酸酯制备出(S)-2-(苯基亚磺酰基)丙烯酸甲酯和(R)-异丙烯酰基甲苯亚砜。在加入 1 % 双(2,4-戊二酮)氧钒(IV) (VOacac2) 催化下，手性 P-甲苯硫代丙醇和丁醇与叔丁基过氧化氢的氧化反应是非对映选择性的（2:1 至 5.5:1）。
• Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides
  作者：Satwinder Singh、Subodh Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0957-4166(01)00434-7

  日期：2001.9

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Diastereoselective oxidation of β-hydroxysulfides with TBHP: a comparative study of titanocenes and Ti(Oi-Pr)4 as catalysts
  作者：Giorgio Della Sala、Stefania Labano、Alessandra Lattanzi、Arrigo Scettri

  DOI：10.1016/s0040-4020(02)00686-5

  日期：2002.8
• Kita, Yasuyuki; Shibata, Norio; Yoshida, Naoki, Journal of the Chemical Society. Perkin transactions I, 1994, # 22, p. 3335 - 3342
  作者：Kita, Yasuyuki、Shibata, Norio、Yoshida, Naoki、Fujita, Shigekazu

  DOI：——

  日期：——
• Selective lipase-catalyzed acylation of epimeric α-sulfinyl alcohols: an efficient method of separation
  作者：Mercedes Medio-Simón、Jesús Gil、Pedro Aleman、Teresa Varea、Gregorio Asensio

  DOI：10.1016/s0957-4166(99)00026-9

  日期：1999.2

  A facile and efficient separation of mixtures of epimeric cc-sulfinyl alcohols 2:3 can be accomplished by selective lipase-catalyzed acylation with neat vinyl acetate. Pseudomonas cepacia and Candida rugosa lipase showed opposite epimer differentiation in the esterification. (C) 1999 Elsevier Science Ltd. All rights reserved.