2-(triethylsilyloxy)ethanethiol | 121405-71-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(triethylsilyloxy)ethanethiol
• 英文别名: Ethanethiol, 2-[(triethylsilyl)oxy]-；2-triethylsilyloxyethanethiol
• CAS: 121405-71-8
• 化学式: C₈H₂₀OSSi
• 分子量: 192.398
• InChiKey: QJKQQGJVHRPFPX-UHFFFAOYSA-N

物化性质

• 沸点：
  62-64 °C(Press: 2 Torr)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  10.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(triethylsilyloxy)ethanethiol 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 methyl 2-acetyloxy-2-(2-triethylsilyloxyethylsulfanyl)acetate
  参考文献：
  名称：

  Enzymatic Resolution of α-acetoxysulfides: A new approach to the synthesis of homochiral S,O-Acetals

  摘要：

  A novel enzymatic resolution of alpha-acetoxysulfides using Pseudomonas fluorescens lipase is reported. Selectivity is highly dependent on the substrate and solvent, with enantiomeric excesses of >95% in some cases. We believe these are the first examples of enzymatic resolutions of an S,O-acetal.

  DOI：

  10.1016/0957-4166(95)00248-n
• 作为产物：
  描述：

  三乙基氯硅烷 、 2-巯基乙醇 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 以52%的产率得到2-(triethylsilyloxy)ethanethiol
  参考文献：
  名称：

  Tunable Thioesters as “Reduction” Responsive Functionality for Traceless Reversible Protein PEGylation

  摘要：

  Disulfide has been the only widely used functionality to serve as a reduction responsive trigger in drug delivery. We introduce thioester as a novel thiol responsive chemistry for drug delivery, whose reactivity can be conveniently modulated by choosing the appropriate steric environment around the thioester. Compared with disulfides, thioesters are facile to synthesize and have an order of magnitude broader kinetic tunability. A novel traceless reversible protein PEGylation reagent is developed based on thioester chemistry.

  DOI：

  10.1021/ja405261u

文献信息

• The first examples of dynamic kinetic resolution by enantioselective acetylation of hemithioacetals: An efficient synthesis of homochiral α-Acetoxysulfides
  作者：Stephen Brand、Martin F. Jones、Christopher M. Rayner

  DOI：10.1016/0040-4039(95)01748-7

  日期：1995.11

  fluorescens lipase catalysed irreversible acetylation of a hemithioacetal using vinyl acetate proceeds via a novel dynamic kinetic resolution. Thus a thiol and an aldehyde are mixed together to form a racemic hemithioacetal, essentially a single enantiomer of which is acylated under the reaction conditions. Racemisation of the unrecognised hemithioacetal by a dissociation-recombination process catalysed by

  的荧光假单胞菌的脂肪酶使用的乙酸乙烯酯进行一硫代半缩醛的催化不可逆的乙酰化通过一种新颖的动态动力学拆分。因此，将硫醇和醛混合在一起以形成外消旋的半硫缩醛，其基本上单一的对映体在反应条件下被酰化。通过硅胶催化的解离-重组过程将未被识别的半硫缩醛消旋化，可以使反应中的转化率大于50％。用合适的底物可以获得高产率和对映选择性。
• Enzymatic resolution of α,β-diacetoxysulfides: Synthesis of optically active O,S-acetals by regiospecific enantioselective primary acetate hydrolysis
  作者：Stephen Brand、Martin F. Jones、Christopher M. Rayner

  DOI：10.1016/s0040-4039(97)00672-2

  日期：1997.5

  α,β-Diacetoxy sulphides are precursors of chiral oxathiolanes and have been resolved by Pseudomonas fluorescens lipase catalysed hydrolysis. The resolution proceeds with complete regioselectivity for the primary acetate and excellent enantioselectivity in most cases.

  α，β-二乙酰氧基硫化物是手性草硫杂环戊烷的前体，并已通过荧光假单胞菌脂肪酶催化水解而分解。在大多数情况下，拆分过程具有对伯乙酸盐的完全区域选择性和出色的对映选择性。
• Catalytic Asymmetric Conjugate Addition of Simple Alkyl Thiols to α,β-Unsaturated <i>N</i>-Acylated Oxazolidin-2-ones with Bifunctional Catalysts
  作者：Yan Liu、Bingfeng Sun、Baomin Wang、Matthew Wakem、Li Deng

  DOI：10.1021/ja8085092

  日期：2009.1.21

  In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis

  在这篇通讯中，我们描述了一种前所未有的高度对映选择性催化共轭加成，在酸碱双功能催化的催化下，简单的烷基硫醇与 α,β-不饱和 N-酰化 oxazolidin-2-ones 进行了加成。该反应为合成光学活性手性硫化合物提供了一种有用的催化方法，否则这些化合物很难通过不对称催化制备。该反应的成功发展源于一项发现，即在适当修饰后，在 6' 位带有硫脲官能团的金鸡纳生物碱可以为不对称共轭加成提供高效催化。
• Heteroatomic derivatives of aziridine. 15. Reaction of 1-(triethylsilyl)- and 1-[2-(trialkylsilyl)ethyl]-aziridines with thiols
  作者：M. G. Voronkov、V. I. Knutov

  DOI：10.1007/bf00633163

  日期：1988.7
• BOPOHKOB, M. G.;KNUTOV, V. I., XIMIYA GETEROTSIKL. SOED.,(1988) N 7, 891-893
  作者：BOPOHKOB, M. G.、KNUTOV, V. I.

  DOI：——

  日期：——