(R)-1-(4-methylsulfanyl-phenyl)-but-3-en-1-ol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-1-(4-methylsulfanyl-phenyl)-but-3-en-1-ol
• 英文别名: (1R)-1-(4-methylsulfanylphenyl)but-3-en-1-ol
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: FOGSRDGMVWIGPN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯基三氯硅烷 、 4-(甲基巯基)苯甲醛 在 (R)-(+)-甲基对甲苯砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-1-(4-methylsulfanyl-phenyl)-but-3-en-1-ol 、 (1S)-1-(4-methylsulfanylphenyl)but-3-en-1-ol
  参考文献：
  名称：

  Chiral sulfoxides as activators of allyl trichlorosilanes in the stereoselective allylation of aldehydes

  摘要：

  手性芳基甲基亚砜在不对称烯丙基化醛与烯丙基三氯硅烷反应中被证明是有效的催化剂。对于电子贫穷的醛，发现了高的对映选择性。高水平的差向选择性及非线性效应的检测使得反应的一些机理方面得以阐明。

  DOI：

  10.1039/c002988b

文献信息

• Enantioselective catalytic addition of allyl organometallic reagents to aldehydes promoted by [Cr(Salen)]: the hidden role played by weak Lewis acids in metallo-Salen promoted reactions
  作者：Marco Bandini、Pier Giorgio Cozzi、Achille Umani-Ronchi

  DOI：10.1016/s0040-4020(00)01047-4

  日期：2001.1

  from NLE study in the [Cr(Salen)] catalysed addition of allyl halides to aldehydes. The results show the key role played by weak Lewis acids in the catalytic system. Weak Lewis acids such as manganese salts and the [Cr(Salen)X] complex drive the stereochemistry of the reaction toward a high level of diastero- and enantioselectivity. Therefore, the Lewis acids and their properties must be taken into

  在本文中，我们介绍了在[Cr（Salen）]催化的烯丙基卤化物加成醛的动力学分析和NLE研究中获得的数据。结果表明弱路易斯酸在催化体系中起关键作用。弱路易斯酸（如锰盐和[Cr（Salen）X]配合物）使反应的立体化学趋向于高水平的非对映选择性和对映选择性。因此，在金属-萨伦介导的过程的合理设计中必须考虑路易斯酸及其性质。
• The First Catalytic Enantioselective Nozaki-Hiyama Reaction
  作者：Marco Bandini、Pier Giorgio Cozzi、Paolo Melchiorre、Achille Umani-Ronchi

  DOI：10.1002/(sici)1521-3773(19991115)38:22<3357::aid-anie3357>3.0.co;2-w

  日期：1999.11.15

  The Nozaki-Hiyama reaction can be performed in an enantioselective catalytic way! The catalytic system utilizes 10 mol % of an inexpensive chiral [Cr(salen)] complex. The [Cr(salen)]/Mn/Me(3)SiCl system effectively promotes the enantioselective addition of allyl chloride to aliphatic and aromatic aldehydes at room temperature (65-89 % ee, 40-60 % yield).

  Nozaki-Hiyama反应可以对映选择性催化方式进行！催化系统利用10 mol％的廉价手性[Cr（salen）]配合物。[Cr（salen）] / Mn / Me（3）SiCl系统可在室温下（65-89％ee，40-60％的收率）有效地促进烯丙基氯向脂族和芳族醛的对映选择性加成。
• New chiral imino- and amino-sulfoxides as activators of allyl trichlorosilane in the asymmetric allylation of aldehydes
  作者：Vincenzo De Sio、Maria Rosaria Acocella、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetasy.2010.04.015

  日期：2010.6

  Chiral 2-methylsulfinyl benzaldehyde proved to be a valuable starting material for a convenient approach towards a variety of imino- and amino-sulfoxides. The catalytic properties of these new ligands, as potential activators of allyl trichlorosilane, have been exploited in new catalytic procedures for the synthesis of enantioenriched homoallylic alcohols. (C) 2010 Elsevier Ltd. All rights reserved.
• Chiral sulfoxides as activators of allyl trichlorosilanes in the stereoselective allylation of aldehydes
  作者：Vincenzo De Sio、Antonio Massa、Arrigo Scettri

  DOI：10.1039/c002988b

  日期：——

  Chiral aryl methyl sulfoxides proved to be efficient activators in the asymmetric allylation of aldehydes with allyl trichlorosilanes. High enantioselectivity was found in the case of electron-poor aldehydes. The high levels of diastereoselectivity and the detection of nonlinear effects have allowed the elucidation of some mechanistic aspects of the reaction.

  手性芳基甲基亚砜在不对称烯丙基化醛与烯丙基三氯硅烷反应中被证明是有效的催化剂。对于电子贫穷的醛，发现了高的对映选择性。高水平的差向选择性及非线性效应的检测使得反应的一些机理方面得以阐明。