(+)-3-(phenylthio)-3-phenylpropionic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+)-3-(phenylthio)-3-phenylpropionic acid
• 英文别名: (-)-3-phenyl-3-(phenylthio)propanoic acid；(3S)-3-phenyl-3-phenylsulfanylpropanoic acid
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: CDSMEKVWCGNQNJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-D-3-O-[(E)-phenyl-prop-2-enoyl]-4-O-trimethylacetyl-1,2:5,6-di-O-isopropylidene-chiro-inositol 在 氢氧化钾 、 正丁基锂 作用下， 以 甲醇 、 正己烷 为溶剂， 生成 (+)-3-(phenylthio)-3-phenylpropionic acid
  参考文献：
  名称：

  作为手性模板的肌醇：将1，4-缀合物加到束缚的肉桂酸酯中。

  摘要：

  将硫代亲核试剂向含有肉桂基Michael受体的手性肌醇中加成1,4-进行了出色的非对映化学诱导和良好的收率。裂解肌醇助剂可提供> 99％ee的β-硫代氢肉桂酸。

  DOI：

  10.1039/b408467e

文献信息

• Chiral auxiliaries and uses thereof
  申请人：Greatrex Ben William

  公开号：US11384094B2

  公开（公告）日：2022-07-12

  The present invention relates to chiral auxiliaries and the syntheses thereof and uses thereof.

  本发明涉及手性助剂及其合成和用途。
• Catalytic Asymmetric 1,6-Michael Addition of Arylthiols to 3-Methyl-4-nitro-5-alkenyl-isoxazoles with Bifunctional Catalysts
  作者：Qing-Lan Pei、Hong-Wei Sun、Zhi-Jun Wu、Xi-Lin Du、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1021/jo2012779

  日期：2011.10.7

  An enantioselective 1,6-Michael addition reaction of arylthiols to a wide range of 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by readily available Takemoto's thiourea catalyst has been developed. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds bearing a 4-nitroisoxazol-5-yl moiety in high to excellent yields (up to 97%) and high enantioselectivities (up to 91% ee). Significantly, the potential utilities of the protocol had been further demonstrated by gram-scale reaction and the versatile conversions of some resulting products into other functionalized and useful compounds.
• CHIRAL AUXILIARIES AND USES THEREOF
  申请人：GREATREX Ben William

  公开号：US20200270267A1

  公开（公告）日：2020-08-27

  The present invention relates to chiral auxiliaries and the syntheses thereof and uses thereof.
• Inositols as chiral templates: 1,4-conjugate addition to tethered cinnamic esters
  作者：Ghislaine Cousins、Andrew Falshaw、John O. Hoberg

  DOI：10.1039/b408467e

  日期：——

  The 1,4-addition of thio nucleophiles to chiro-inositols containing a cinnamyl Michael acceptor proceeded with excellent diastereochemical induction and good yields. Cleavage of the inositol auxiliary provides beta-thio hydrocinnamic acids in >99% ee's.

  将硫代亲核试剂向含有肉桂基Michael受体的手性肌醇中加成1,4-进行了出色的非对映化学诱导和良好的收率。裂解肌醇助剂可提供> 99％ee的β-硫代氢肉桂酸。