(R_S)-3,3-difluoro-1-<(4-methylphenyl)sulphinyl>-4,4,4-trifluoro-butane-2,2-diol | 105984-81-4

• 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: (R_S)-3,3-difluoro-1-<(4-methylphenyl)sulphinyl>-4,4,4-trifluoro-butane-2,2-diol
• 英文别名: 1,1-difluoro-3-[(R)-(4-methylphenyl)sulfinyl]propane-2,2-diol
• CAS: 105984-81-4
• 化学式: C₁₀H₁₂F₂O₃S
• 分子量: 250.266
• InChiKey: WCZPOPDAPUUSBS-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R_S)-3,3-difluoro-1-<(4-methylphenyl)sulphinyl>-4,4,4-trifluoro-butane-2,2-diol 在 4 Angstroems MS 、 二异丁基氢化铝 作用下， 以60%的产率得到(2S)-1,1-difluoro-3(R)-<(4-methylphenyl)sulfinyl>propan-2-ol
  参考文献：
  名称：

  Stereoselection Parameters and Theoretical Model in the Enantioselective Protonation of Enolates with α-Sulfinyl Alcohols

  摘要：

  The effects of the solvent, temperature, presence of Lithium salts in the medium, and acidity of the proton source on enantioselective protonation with alpha-sulfinyl alcohols 2a-e were studied. Stereoselectivity was generally enhanced when lithium bromide was present in the medium during enolization and also with the use of methylene chloride solutions. Conversely, the optimal reaction temperature varied with the alpha-sulfinyl alcohol used as a proton source, and its effect appears to be related to both the acidity of the proton source and the enolate structure. alpha-Sulfinyl alcohols 2a and 2b gave the best results when the reactions were carried out at -100 degrees C, while the optimal temperature with 2c was -78 degrees C. The same ee values were obtained with 2d and 2e at either -100 or -78 degrees C. In addition, an efficient synthesis of alpha-sulfinyl alcohols 2b and 2e is described.

  DOI：

  10.1021/jo981294y
• 作为产物：
  描述：

  二氟乙酸 、 (R)-(+)-甲基对甲苯砜 生成 (R_S)-3,3-difluoro-1-<(4-methylphenyl)sulphinyl>-4,4,4-trifluoro-butane-2,2-diol
  参考文献：
  名称：

  A Convenient Synthesis of 3-Fluorinated 2-Oxopropyl Sulphoxides from Fluorinated Lithium Acetates and 1-Lithioalkyl Sulphoxides

  摘要：

  光学纯的 4-甲基苯基亚砜甲基和 4-甲基苯基亚砜乙基与二异丙基酰胺锂发生金属化反应，然后与氟化乙酸锂或乙酸酯发生反应。C-酰化反应顺利进行，并具有区域选择性，从而得到高产率的手性 3-氟化 2-氧代丙基 4-甲基苯基亚砜。二甲基亚砜与氟化乙酸锂发生类似反应，可以得到外消旋 3-氟化 2-氧代丙基甲基亚砜。作为产品进一步反应的实例，介绍了 3-氟-2-氧代丙基 4-甲基苯基亚砜的 C-甲基化、S-脱氧和羰基还原反应。

  DOI：

  10.1055/s-1986-31714

文献信息

• Stereoselective synthesis of optically pure γ-fluoro-β-enaminosulfoxides and reduction to γ-fluoro-β-aminosulfoxides
  作者：Pierfrancesco Bravo、Marcello Crucianelli、Matteo Zanda

  DOI：10.1016/0040-4039(95)00422-9

  日期：1995.4

  The aza-Wittig reaction of phospha-λ5-azenes with optically pure γ-fluorosubstituted β-ketosulfoxides leads to the corresponding β-enaminosulfoxides, which were easily isolated in diastereomerically pure form. The stereoselective reduction of the enamine 3cb afforded the optically pure β-sulphinyl-amine 5cb in high overall yield.

  phospha-的氮杂Wittig反应λ 5 -azenes与光学纯γ-β氟取代的- ketosulfoxides通向相应β-enaminosulfoxides，将其容易地在对映异构纯形式分离。烯胺3cb的立体选择性还原以高的总收率提供了光学纯的β-亚磺酰基胺5cb。
• New fluorinated chiral synthons
  作者：Pierfrancesco Bravo、Alessandra Farina、Massimo Frigerio、Stefano Valdo Meille、Fiorenza Viani、Vadim Soloshonok

  DOI：10.1016/0957-4166(94)80049-9

  日期：1994.6

  The syntheses of new optically pure poly-halo and poly-fluoro oxiranes 5b-e by addition of diazomethane on the corresponding beta-keto-gamma-fluorosubstituted sulphoxide intermediates, both in keto 3, hydrate 4 or in keto/ hydrate form are described. Syntheses of sulphur-free fluorinated oxiranes 18b-e, beta-hydroxy-beta-trifluoromethyl amine 21d, alpha-hydroxy-alpha-trifluoromethyl-beta-amino acid 24d, alpha-trifluoromethyl-alpha,beta-dihydroxy acid 25d and beta,gamma-dihpdroxy-beta-trifluoro- and -chlorodifluoromethyl amines 26c and 26d are shown as examples of their chemical versatility
• Stereoselection Parameters and Theoretical Model in the Enantioselective Protonation of Enolates with α-Sulfinyl Alcohols
  作者：Gregorio Asensio、Pedro Aleman、Jesus Gil、Luis R. Domingo、Mercedes Medio-Simon

  DOI：10.1021/jo981294y

  日期：1998.12.1

  The effects of the solvent, temperature, presence of Lithium salts in the medium, and acidity of the proton source on enantioselective protonation with alpha-sulfinyl alcohols 2a-e were studied. Stereoselectivity was generally enhanced when lithium bromide was present in the medium during enolization and also with the use of methylene chloride solutions. Conversely, the optimal reaction temperature varied with the alpha-sulfinyl alcohol used as a proton source, and its effect appears to be related to both the acidity of the proton source and the enolate structure. alpha-Sulfinyl alcohols 2a and 2b gave the best results when the reactions were carried out at -100 degrees C, while the optimal temperature with 2c was -78 degrees C. The same ee values were obtained with 2d and 2e at either -100 or -78 degrees C. In addition, an efficient synthesis of alpha-sulfinyl alcohols 2b and 2e is described.
• A Convenient Synthesis of 3-Fluorinated 2-Oxopropyl Sulphoxides from Fluorinated Lithium Acetates and 1-Lithioalkyl Sulphoxides
  作者：Pierfrancesco Bravo、Elena Piovosi、Giuseppe Resnati

  DOI：10.1055/s-1986-31714

  日期：——

  Optically pure methyl 4-methylphenyl sulphoxide and ethyl 4-methylphenyl sulphoxide are metallated with lithium diisopropylamide and then subjected to the reaction with fluorinated lithium acetates or acetic esters. C-Acylation proceeds smoothly and regioselectively to give high yields of chiral 3-fluorinated 2-oxopropyl 4-methylphenyl sulphoxides. The analogous reaction of dimethyl sulphoxide with fluorinated lithium acetates affords good yields of racemic 3-fluorinated 2-oxopropyl methyl sulphoxides. As examples of further reactions of the products, C-methylation, S-deoxygenation, and carbonyl reduction of 3-fluoro-2-oxopropyl 4-methylphenyl sulphoxide are described.

  光学纯的 4-甲基苯基亚砜甲基和 4-甲基苯基亚砜乙基与二异丙基酰胺锂发生金属化反应，然后与氟化乙酸锂或乙酸酯发生反应。C-酰化反应顺利进行，并具有区域选择性，从而得到高产率的手性 3-氟化 2-氧代丙基 4-甲基苯基亚砜。二甲基亚砜与氟化乙酸锂发生类似反应，可以得到外消旋 3-氟化 2-氧代丙基甲基亚砜。作为产品进一步反应的实例，介绍了 3-氟-2-氧代丙基 4-甲基苯基亚砜的 C-甲基化、S-脱氧和羰基还原反应。