(R)-甲基正丙基亚砜 | 37177-70-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 中文名称: (R)-甲基正丙基亚砜
• 英文名称: (R)-methyl n-propyl sulfoxide
• 英文别名: 1-[(R)-methylsulfinyl]propane
• CAS: 37177-70-1
• 化学式: C₄H₁₀OS
• 分子量: 106.189
• InChiKey: WOBARLJSXVAEGX-ZCFIWIBFSA-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 styrene monooxygenase 、 还原型辅酶II(NADPH)四钠盐 、 葡萄糖 、 MSDKIKHVTDASFEADVLQAQGPVLVDYWAEWCGPCKMIAPVLDDIAATYEGKLTVAKLNIDENQETPAKHGVRGIPTLMLFKNGNVEATKVGALSKSQLAAFLDAHL 、 MSEVRHSRVIILGSGPAGYSAAVYAARANLKPLLITGMQAGGQLTTTTEVDNWPGDPHGLTGPALMQRMQEHAERFETEIVFDHINAVDLANKPFTLQGDSGKYTCDALIIATGASARYLGLPSEETFMGKGVSACATCDGFFYRNKPVAVVGGGNTAVEEALYLANIASKVTLVHRRDTFRAEKILVDKLHARVAEGKIELKLNATLDEVLGDNMGVTGARLKNNDGSSDEIKVDGVFIAIGHTPNTSLFEGQLTLKDGYLVVNGGREGNATATNIEGVFAAGDVADHVYRQAITSAGAGCMAALDVERYLDGLANASF 、 MVLRSEILVNKNVMPTAEQALPGRETPMSLPEFHYVFKDTPLLGPFFEGAIDFAIFGLGCFWGAERRFWQREGVVSTVVGYAGGFTPHPTYEEVCSGLTGHTEVVLVVFDKDRVSYRELLAMFWELHNPTQGMRQGNDIGTQYRSAIYCTSPEQLEQAKASRDAFQAELSKAGFGEITTEIDQAPTVYFAEAYHQQYLAKNPDGYCGIGGTGVCLPPSLQGN 、 MYPDLKGKVVAITGAASGLGKAMAIRFGKEQAKVVINYYSNKQDPNEVKEEVIKAGGEAVVVQGDVTKEEDVKNIVQTAIKEFGTLDIMINNAGLENPVPSHEMPLKDWDKVIGTNLTGAFLGSREAIKYFVENDIKGNVINMSSVHEVIPWPLFVHYAASKGGIKLMTETLALEYAPKGIRVNNIGPGAINTPINAEKFADPKQKADVESMIPMGYIGEPEEIAAVAAWLASKEASYVTGITLFADGGMTQYPSFQAGRG 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 以90%的产率得到(R)-甲基正丙基亚砜
  参考文献：
  名称：

  具有辅助因子再生的多酶氧化还原系统用于亚砜的循环脱消旋

  摘要：

  建立了辅因子再生的多酶循环去外消旋体系，用于制备对映体纯亚砜。通过蛋氨酸亚砜还原酶 (Msr)、苯乙烯单加氧酶 (SMO) 和其他三种辅助酶（Trx、Trx-R 和 GDH）的级联催化，以 >90% 的产率和 >90%的ee制备手性亚砜。

  DOI：

  10.1002/anie.202209272

文献信息

• 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
• Synthesis of enantiomerically pure alkyl and aryl methyl sulfoxides from cholesteryl methanesulfinates
  作者：Kenneth K. Andersen、Bogdan Bujnicki、Jozef Drabowicz、Marian Mikolajczyk、John B. O'Brien

  DOI：10.1021/jo00195a042

  日期：1984.10
• 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.