(2S,R_S)-1-(4-methylphenyl)sulfinyl-3,3,3-trifluoropropan-2-ol | 113965-66-5

• 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: (2S,R_S)-1-(4-methylphenyl)sulfinyl-3,3,3-trifluoropropan-2-ol
• 英文别名: (Sc,Rs)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanol；(2S)-1,1,1-trifluoro-3-[(R)-(4-methylphenyl)sulfinyl]propan-2-ol
• CAS: 113965-66-5
• 化学式: C₁₀H₁₁F₃O₂S
• 分子量: 252.257
• InChiKey: GLIYKUFNDONAPU-JDNHERCYSA-N

物化性质

• 沸点：
  380.4±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  6

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 (2S,R_S)-1-(4-methylphenyl)sulfinyl-3,3,3-trifluoropropan-2-ol 在 lithium diisopropyl amide 作用下， 生成 1-((R)-(S)-2-Benzyloxy-3,3,3-trifluoro-propane-1-sulfinyl)-4-methyl-benzene
  参考文献：
  名称：

  采用（R ; E）-3,3,3-三氟丙-1-烯基对甲苯基亚砜的高度立体选择性不对称迈克尔加成反应

  摘要：

  由三氟乙酸乙酯分三步制备的（R；E）-3,3,3-三氟丙-1-烯基对甲苯基亚砜在与烯醇盐的迈克尔加成反应中显示出高度的非对映选择性；通过这种方式，可以容易地以高收率和高光学纯度获得光学活性的三氟甲基化的有机分子。

  DOI：

  10.1039/c39870001340
• 作为产物：
  描述：

  (R)-(+)-甲基对甲苯砜 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2S,R_S)-1-(4-methylphenyl)sulfinyl-3,3,3-trifluoropropan-2-ol
  参考文献：
  名称：

  采用（R ; E）-3,3,3-三氟丙-1-烯基对甲苯基亚砜的高度立体选择性不对称迈克尔加成反应

  摘要：

  由三氟乙酸乙酯分三步制备的（R；E）-3,3,3-三氟丙-1-烯基对甲苯基亚砜在与烯醇盐的迈克尔加成反应中显示出高度的非对映选择性；通过这种方式，可以容易地以高收率和高光学纯度获得光学活性的三氟甲基化的有机分子。

  DOI：

  10.1039/c39870001340
• 作为试剂：
  描述：

  Lithium;2-methyl-3,4-dihydronaphthalen-1-olate 在 (2S,R_S)-1-(4-methylphenyl)sulfinyl-3,3,3-trifluoropropan-2-ol 、 lithium bromide 、 lithium tert-butoxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-methyl-1-tetralone 、 (2S)-2-methyl-1-tetralone
  参考文献：
  名称：

  Remarkable effect of lithium bromide in the enantioselective protonation with α-sulfinyl alcohols

  摘要：

  The favourable effect of lithium bromide enhancing the facial enantioselectivity in the protonation of methyl tetralone enolate with alpha-sulfinyl alcohols is described. Theoretical calculations allow to propose a model to explain the stereochemical course of the protonation reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00469-9

文献信息

• Synthesis of (<i>R</i>c,<i>S</i>s)-1,1,1-Trifluoro-3-(<i>p</i>-tolylsulfinyl)-2-propanol by an Asymmetric Reduction with a Yeast,<i>Yamadazyma farinosa</i>, as a Key-step
  作者：Atsushi Sakai、Mikio Bakke、Hiromichi Ohta、Hiroshi Kosugi、Takeshi Sugai

  DOI：10.1246/cl.1999.1255

  日期：1999.11

  (>99% e.e.), an important reagent for the asymmetric protonation of substituted enolates, was prepared (70%) from (S)-methyl p-tolyl sulfoxide. The stereoselectivity of the Yamdazyma farinosa-catalyzed reduction of carbonyl groups, the key step for the introduction of an asymmetric carbon, was greatly affected by the stereochemistry of the asymmetric sulfur atom. The reduction of (S)-1,1,1-trifluor

  (Rc,Ss)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanol (>99% ee)，一种用于取代烯醇不对称质子化的重要试剂，由 (70%) 制备(S)-甲基对甲苯基亚砜。Yamdazyma farinosa 催化的羰基还原是引入不对称碳的关键步骤，其立体选择性受不对称硫原子的立体化学影响很大。(S)-1,1,1-三氟-3-(对甲苯基亚磺酰基)-2-丙酮的还原以相当立体选择性的方式顺利进行，得到所需化合物，而 (Rc, Rs)-和(Sc,Rs)-异构体是从具有相反(R)-构型的底物获得的。
• Homochiral Perfluoroalkyl-Group-Substituted Secondary Alcohols Through Stereoselective Reduction of Perfluoroalkyl 1-(<i>p</i>-Tolylsulfinyl)alkyl Ketones
  作者：Pierfrancesco Bravo、Massimo Frigerio、Giuseppe Resnati

  DOI：10.1055/s-1988-27764

  日期：——

  The reduction of some enantiomerically pure perfluoroalkyl α-(p-tolylsulfinyl) ketones was performed. Alcohols containing perfluoroalkyl and p-tolylsulfinyl groups were obtained with high diastereoselection when a phenyl residue was present on the sulfinylated carbon and with lower diastereoselection in the other cases. Removal of the chiral sulfinyl group from single diastereoisomers gave secondary alcohols containing a perfluoroalkyl group in enantiomerically pure form.

  对某些对映纯的全氟烷基 α-(对甲苯亚磺酰基)酮进行了还原。当亚磺酰基碳上存在苯基残基时，含有全氟烷基和对甲苯亚磺酰基的醇类具有高立体选择性，而在其他情况下具有较低立体选择性。从单一非对映异构体中去除手性亚磺酰基，得到含有全氟烷基的对映纯的仲醇。
• Synthesis of (S)-.beta.,.beta.,.beta.-trifluorolactic acid and (S)-.alpha.-methoxy-.alpha.-(trifluoromethyl)phenylacetic acid from (R)-methyl p-tolyl sulfoxide
  作者：Pierfrancesco Bravo、Massimo Frigerio、Giuseppe Resnati

  DOI：10.1021/jo00300a051

  日期：1990.6
• 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.
• Kosugi, Hiroshi; Hoshino, Kunihide; Uda, Hisashi, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 401 - 402
  作者：Kosugi, Hiroshi、Hoshino, Kunihide、Uda, Hisashi

  DOI：——

  日期：——