(RsSc)-1-(p-tolylsulfinyl)-2-phenyl-2-propanol | 52117-57-4

• 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: (RsSc)-1-(p-tolylsulfinyl)-2-phenyl-2-propanol
• 英文别名: <2S,(S)R>-2-phenyl-1-p-tolylsulfinylpropan-2-ol；<2S,(S)R>-2-phenyl-1-(4'-methylphenylsulfinyl)-2-propanol；(2S)-1-[(R)-(4-methylphenyl)sulfinyl]-2-phenylpropan-2-ol
• CAS: 52117-57-4
• 化学式: C₁₆H₁₈O₂S
• 分子量: 274.384
• InChiKey: QGVFYRLKYHUTKS-VQIMIIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  三甲基铝 、 (R)-p-tolylsulfinylacetophenone 在 zinc(II) chloride 作用下， 生成 (RsSc)-1-(p-tolylsulfinyl)-2-phenyl-2-propanol 、 (RsRc)-1-(p-tolylsulfinyl)-2-phenyl-2-propanol
  参考文献：
  名称：

  Catalytic activity of chiral β-hydroxysulfoxides in the enantioselective addition of diethylzinc to benzaldehyde.

  摘要：

  The first examples of the use of readily available beta-hydroxysulfoxides 1-8 as chiral catalysts in the enantioselective addition of diethylzinc to benzaldehyde are reported. The increase of the steric hindrance around the chiral ligand OH group improves the e.e. of the obtained 1-phenylpropanol, which is higher with tertiary alcohols (25-45%) than with secondary ones (<23%). The addition of MeAl3 also affords better e.e. (55%).

  DOI：

  10.1016/s0957-4166(00)80181-0

文献信息

• Substituent Effect on the Enantioface-Differentiating Reaction of (<i>R</i>)-[Lithiomethyl<i>p</i>-Tolyl Sulfoxide] with<i>m</i>- or<i>p</i>-Substituted Acetophenones
  作者：Norio Kunieda、Junzo Nokami、Masayoshi Kinoshita

  DOI：10.1246/bcsj.65.526

  日期：1992.2

  When lithiomethyl p-tolyl sulfoxide derived from (R)-(+)-[methyl p-tolyl sulfoxide] was allowed to react with acetophenones which have a variety of m- or p-substituents, the corresponding diastereometic mixture of β-hydroxy sulfoxides (RsSc and RsRc) was produced. The degree of enantioselectivity was affected by the nature of the substituent on benzene ring. The logarithms of the RsSc/RsRc values thus

  当衍生自 (R)-(+)-[甲基对甲苯亚砜]的硫代甲基对甲苯亚砜与具有多种间或对位取代基的苯乙酮反应时，相应的β-羟基亚砜的非对映混合物(RsSc 和 RsRc) 产生。对映选择性的程度受苯环上取代基的性质影响。由此获得的 RsSc/RsRc 值的对数与哈米特的 σ 值具有良好的相关性，提供了一条负直线。已经根据反应的立体化学来源讨论了结果。
• Diastereofacial Control in the Reaction of (R)-α-(<i>p</i>-Tolylsulfinyl)acetophenones with Several Organometallics
  作者：Tamotsu Fujisawa、Atsushi Fujimura、Yutaka Ukaji

  DOI：10.1246/cl.1988.1541

  日期：1988.9.5

  controlled addition of organometallics to optically active β-ketosulfoxide was achieved to furnish both diastereomers of β-hydroxy sulfoxide depending on the selection of organometallic reagents. Trichloromethyltitanium added to (R)-α-(p-tolylsulfinyl)acetophenones to give (RsRc)-β-hydroxy sulfoxides, while (RsSc)-β-hydroxy sulfoxides were obtained by utilizing trimethylaluminum. The utility of the present

  根据有机金属试剂的选择，实现了有机金属向旋光β-酮亚砜的非对映控制加成以提供β-羟基亚砜的两种非对映异构体。三氯甲基钛加入到（R）-α-（对甲苯基亚磺酰基）苯乙酮中得到（RsRc）-β-羟基亚砜，而（RsSc）-β-羟基亚砜则是利用三甲基铝得到的。本反应的效用在sydowic酸的两种对映异构体的合成中得到证明。
• Stereoselective reactions of AlMe3 with chiral acyclic β-ketosulfoxides.
  作者：M.Carmen Carreño、José L García Ruano、M.Carmen Maestro、Manuel Pérez González、Ana B Bueno、Jean Fischer

  DOI：10.1016/s0040-4020(01)80254-4

  日期：1993.1

  The results obtained in the addition reactions of AlMe3 to acyclic beta-ketosulfoxides 1-5 are described. In the presence of ZnX2 (X=Cl,Br) reactions proceed in high yield. The diastereoselectivities achieved, ranging from 70% to 90%, make these reactions useful for the asymmetric synthesis of tertiary methyl carbinols.