(2S,3R)-3-Hydroxy-2-methyl-3-phenyl-thiopropionic acid S-pyridin-2-yl ester

• 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,3R)-3-Hydroxy-2-methyl-3-phenyl-thiopropionic acid S-pyridin-2-yl ester
• 英文别名: S-pyridin-2-yl (2S,3R)-3-hydroxy-2-methyl-3-phenylpropanethioate
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: ZMRUITBTNJKVEZ-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基吡啶 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3R)-3-Hydroxy-2-methyl-3-phenyl-thiopropionic acid S-pyridin-2-yl ester
  参考文献：
  名称：

  Diastereoselective aldol condensation of directly generated titanium enolates of activated esters.

  摘要：

  Simply generated (TiCl4, Et3N, -78-degrees-C) titanium enolates of some thioesters and alpha-thio substituted esters undergo aldol condensations with achiral and chiral aldehydes with low to high stereoselectivity. An H-1-NMR study of the TiCl4/ester complexation and of the enolization process is presented. The relation between the enolate structure and the aldol product stereochemistry is discussed.

  DOI：

  10.1016/s0040-4020(01)81945-1

文献信息

• A CONVENIENT METHOD FOR GENERATION OF TIN(II) THIOESTER ENOLATE AND ITS REACTION WITH ALDEHYDE
  作者：Teruaki Mukaiyama、Noritsugu Yamasaki、Rodney W. Stevens、Masahiro Murakami

  DOI：10.1246/cl.1986.213

  日期：1986.2.5

  Tin(II) enolates of thioesters are conveniently generated by the addition of stannous thiolates to ketenes. The tin(II) enolates thus formed react with aldehydes to afford the corresponding β-hydroxythioesters in a syn-selective manner. And this method is applied to an enantioselective formation of β-hydroxythioesters by the use of a chiral diamine as ligand.

  硫酯的锡 (II) 烯醇化物可以通过将硫醇亚锡添加到烯酮中方便地生成。由此形成的锡 (II) 烯醇化物与醛反应以顺选择性方式提供相应的 β-羟基硫酯。并且该方法通过使用手性二胺作为配体而应用于β-羟基硫酯的对映选择性形成。
• Diastereoselective aldol condensation of silyl ketene acetal of 2-pyridyl thioester with benzaldehyde
  作者：Kwee-Hyun Suh、Dong-Joon Choo

  DOI：10.1016/0040-4039(95)01231-6

  日期：1995.8

  The TiCl4-mediated aldol reaction of the (E)-O-silyl ketene-O,S-acetal derived from 2-pyridyl thioester with benzaldehyde gave exclusively syn-aldol product. In contrast, BF3-mediated reaction afforded the corresponding anti-isomer as a major product. Chelation and acyclic transition state are postulated in order to explain the observed selectivities.

  由2-吡啶基硫酯衍生的（E）-O-甲硅烷基烯酮-O，S-缩醛与苯甲醛的TiCl 4介导的醇醛缩合反应仅得到顺式-醛醇缩合产物。相反，BF 3介导的反应提供了相应的反异构体作为主要产物。假定螯合和无环过渡态是为了解释观察到的选择性。