1-((S)-甲磺酰基)-丙烷 | 26613-86-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 中文名称: 1-((S)-甲磺酰基)-丙烷
• 英文名称: 1-((S)-Methanesulfinyl)-propane
• 英文别名: 1-[(S)-methylsulfinyl]propane
• CAS: 26613-86-5
• 化学式: C₄H₁₀OS
• 分子量: 106.189
• InChiKey: WOBARLJSXVAEGX-LURJTMIESA-N

物化性质

• 沸点：
  212.0±9.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正辛基丙基硫醚 在 双氧水 、 (S,S)-4,4'-azanediylbis(2,6-bis(2,4,6-triheptylphenyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide) 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以98%的产率得到1-((S)-甲磺酰基)-丙烷
  参考文献：
  名称：

  具有可调节限制和酸度的亚胺二磷酸型布朗斯台德酸的统一方法

  摘要：

  我们设计并实现了一种高效且操作简单的单烧瓶合成基于亚胺二磷酸盐的布朗斯台德酸。该方法通过六氯双磷鎓盐的连续氯化物取代进行，提供对亚胺二磷酸盐 (IDP)、亚氨基亚胺二磷酸盐 ( i IDP) 和亚胺二磷亚胺酸盐 (IDPi) 的快速访问。这些特殊的酸催化剂具有广泛的酸度范围（在 MeCN 中p K a从~11 到 <2）和易于调节的受限活性位点。我们的方法能够获得以前难以捉摸的具有特别高结构限制的催化剂支架，其中一个催化甲基n的第一个高度对映选择性 (>95:5 er) 磺化-丙基硫醚。此外，该方法提供了一种新颖、合理设计的超酸性催化剂基序，即亚氨基二磷（亚氨基磺酰基亚氨基）亚胺酸酯（IDPii），其极端反应性超过了常用的超布朗斯台德酸，如三氟甲磺酸。一种此类 IDPii 催化剂的独特反应性已在甲硅烷基乙烯酮缩醛与作为亲电烷基化试剂的甲醇的第一次 α-甲基化反应中得到证明。

  DOI：

  10.1021/jacs.1c07067

文献信息

• Kinetic resolution of sulfoxides with high enantioselectivity by a new homologue of methionine sulfoxide reductase B
  作者：Yuyan Zhao、Xu Jiang、Shihuan Zhou、Jin Tian、Piao Yang、Yanli Chen、Quan Zhang、Xianlin Xu、Yong-Zheng Chen、Jiawei Yang

  DOI：10.1039/d3ob00402c

  日期：——

  activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the S configuration were prepared in approximately 50% yield and 92–99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L−1). This study presents an efficient route for the enzymatic preparation of (S)-sulfoxides

  光学纯亚砜是值得注意的化合物，在各个工业领域都有广泛的应用。在这里，我们报告了一种甲硫氨酸亚砜还原酶 B (MsrB) 同系物，它在外消旋 ( rac ) 亚砜的动力学拆分中表现出高对映选择性和广泛的底物范围。这种 MsrB 同系物，命名为li MsrB，是从Limnohabitans sp. 中鉴定出来的。103DPR2 并显示出良好的活性以及对一系列芳族、杂芳族、烷基和硫代烷基亚砜的对映选择性。S构型的手性亚砜通过动力学拆分以高达 90 mM（11.2 g L -1). 本研究提出了一种通过动力学拆分酶促制备 ( S )-亚砜的有效途径。
• Synthesis of Chiral Sulfoxides by A Cyclic Oxidation‐Reduction Multi‐Enzymatic Cascade Biocatalysis
  作者：Jin Tian、Shihuan Zhou、Yanli Chen、Yuyan Zhao、Song Li、Piao Yang、Xianlin Xu、Yongzheng Chen、Xiaoling Cheng、Jiawei Yang

  DOI：10.1002/chem.202304081

  日期：2024.4.2

  An unconventional biocatalytic oxidation-reduction cascade system with cofactor regeneration was established for the synthesis of enantiopure sulfoxides using prochiral sulfildes as substrates. Heteroaryl alkyl, aryl alkyl and dialkyl sulfoxides in R configuration were prepared in >90 % conversion with >90 % ee through the cascade catalysis of MsrA, Fus-SMO and three other auxiliary enzymes (Trx, Trx-R

  建立了一种具有辅因子再生的非常规生物催化氧化还原级联系统，用于以前手性硫醚为底物合成对映体纯亚砜。通过 MsrA、Fus-SMO 和其他三种辅助酶（Trx、Trx-R 和 GDH）的级联催化，制备了R构型的杂芳基烷基、芳基烷基和二烷基亚砜，转化率 >90% ， ee >90%。
• New oxyfunctionalization capabilities for .omega.-hydroxylases. Asymmetric aliphatic sulfoxidation and branched ether demethylation
  作者：Andreas G. Katopodis、Homer A. Smith、Sheldon W. May

  DOI：10.1021/ja00211a033

  日期：1988.2.3
• Asymmetric synthesis of alkane- and arenesulfinates of diacetone-D-glucose (DAG): an improved and general route to both enantiomerically pure sulfoxides
  作者：I. Fernandez、N. Khiar、J. M. Llera、F. Alcudia

  DOI：10.1021/jo00051a022

  日期：1992.12

  Diacetone-D-glucose (DAG), a commercially available, sugar-derived secondary alcohol, was found to react with alkane- and arenesulfinyl chlorides in the presence of a tertiary amine in a very useful manner. When i-Pr2Net is used as the base, (-)-(S)-alkane- and arenesulfinates are obtained in 50-90% yield with 89-greater-than-or-equal-to 95% de. Simply changing the base from i-Pr2NEt to Py affords (+)-(R)-alkane- and arenesulfinates in 56-87% yield with 70-greater-than-or-equal-to 95% de. The de's were determined by H-1 NMR. Optically pure alkane- and arenesulfinates are obtained either by recrystallization or by column chromatography. These sulfinates were transformed into various enantiomerically pure sulfoxides (alkyl alkyl and alkyl aryl) by reaction with different Grignard reagents. This new methodology is cheap, quick, and very convenient when both enantiomers of a given sulfoxide are needed enantiomerically pure. The influence of the solvent, as well as the effect of other types of bases, on the stereochemical course of the reaction has been evaluated, and a possible origin of the diastereoselectivity is discussed. Other optically pure secondary alcohols are used m the same reaction, and the comparison of their behavior with that of DAG is also reported.
• An efficient synthesis of both enantiomers of chiral non racemic methylsulfoxides from DAG
  作者：José M. Llera、Inmaculada Fernández、Felipe Alcudia

  DOI：10.1016/0040-4039(91)80503-x

  日期：1991.12

  Diacetone-D-Glucose is stereoselectively converted to its (S)- or (R)-methanesulfinates 1 and 2 in 90 and 87% yield by treatment with methylsulfinyl chloride in the presence of diisopropylethylamine or pyridine, respectively. After purification, sulfinates 1 and 2 were transformed into both epimers of enantiomerically pure methylsulfoxides by reaction with Grignard reagents.