(1R,2S)-2-methylsulfanylthioxocarbonyloxycyclopentanecarboxylic acid ethyl ester | 162084-62-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (1R,2S)-2-methylsulfanylthioxocarbonyloxycyclopentanecarboxylic acid ethyl ester
• 英文别名: (1R,2S)-ethyl 2-(((methylthio)carbonothioyl)oxy)cyclopentanecarboxylate；ethyl (1R,2S)-2-methylsulfanylcarbothioyloxycyclopentane-1-carboxylate
• CAS: 162084-62-0
• 化学式: C₁₀H₁₆O₃S₂
• 分子量: 248.367
• InChiKey: CBBCDFAGFVLWBA-SFYZADRCSA-N

物化性质

• 沸点：
  336.4±31.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-methylsulfanylthioxocarbonyloxycyclopentanecarboxylic acid ethyl ester 在 咪唑 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 (R)-1-tert-butyldimethylsilyloxymethylcyclopent-2-ene
  参考文献：
  名称：

  Regioselective Synthesis of α-Methyl 2-Methyleneglutarate via a Novel Lactonization−Elimination Rearrangement

  摘要：

  A facile route to the alpha-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of O-silyl 2-(hydroxy-methyl)dimethylglutarate.

  DOI：

  10.1021/jo051854a
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 (1R,2S)-2-methylsulfanylthioxocarbonyloxycyclopentanecarboxylic acid ethyl ester
  参考文献：
  名称：

  (R)-(2-环戊烯基)甲醇的制备及(8R,11R)-Precapnelladiene的首次全合成

  摘要：

  从 2-氧代环戊烷羧酸乙酯制备对映纯的 (R)-(2-环戊烯基) 甲醇 (2)。2 与 4,4-二甲基-3-苯硫基-2-环己烯酮偶联得到烯醇醚，其...

  DOI：

  10.1246/bcsj.67.2880

文献信息

• Preparation of (<i>R</i>)-(2-Cyclopentenyl)methanol and the First Total Synthesis of (8<i>R</i>,11<i>R</i>)-Precapnelladiene
  作者：Koji Maeda、Yoshinobu Inouye

  DOI：10.1246/bcsj.67.2880

  日期：1994.10

  Enantiometrically pure (R)-(2-cyclopentenyl)methanol (2) was prepared from ethyl 2-oxocyclopentanecarboxylate. Coupling of 2 with 4,4-dimethyl-3-phenylthio-2-cyclohexenone gave an enol ether, which...

  从 2-氧代环戊烷羧酸乙酯制备对映纯的 (R)-(2-环戊烯基) 甲醇 (2)。2 与 4,4-二甲基-3-苯硫基-2-环己烯酮偶联得到烯醇醚，其...
• Beta-amino acids
  申请人：Gellman H. Samuel

  公开号：US20070123709A1

  公开（公告）日：2007-05-31

  Disclosed are β-amino acid monomers containing cylcoalkyl, cycloalkenyl, and heterocylic substituents which encompass the α and β carbons of the peptide backbone and β-polypeptides made from such monomers. Method of generating combinatorial libraries of polypeptides containing the β-peptide residues and libraries formed thereby are disclosed.

  本发明涉及包含环烷基、环烯基和杂环取代基的β-氨基酸单体，其包括肽骨架的α和β碳，以及由这样的单体制成的β-多肽。还公开了生成含β-肽残基的多肽组合库的方法以及由此形成的库。
• Synthesis of Isopeptide Epoxide Peptidomimetics
  作者：Debatosh Majumdar、Matthew D. Alexander、James K. Coward

  DOI：10.1021/jo801907p

  日期：2009.1.16

  Two epoxide-containing peptidomimetics of the isopeptide, glutatnyl-gamma-glutamate, have been synthesized via a route that should be generally applicable to the synthesis of isopeptide analogues in which an oxirane replaces the scissile peptide bond. Enzymes that catalyze the hydrolysis of peptides and isopeptides are often susceptible to inactivation by electrophilic substrate analogues. In this research, an epoxide was installed as an electrophilic replacement of the scissile isopeptide bond. The C-terminal glutamyl mimic was accessed by the stereospecific synthesis of suitably substituted cyclopentenes, 8 and 10, as surrogates for either the L- or D- enantiomer. The enantiomeric cyclopentenes were further elaborated to incorporate an appended sulfone that was reacted with a suitably protected glutamyl-gamma-semialdehyde in a Julia-Kocienski olefination reaction. This olefination afforded predominantly the desired E-olefin isosteres of L-glutamyl-gamma-D-glutamate and L-glutamyl-gamma-L-glutamate, following which peracid-mediated epoxidation and deprotection provided the epoxide-containing peptidomimetics, 4 and 5.
• US8772450B2
  申请人：——

  公开号：US8772450B2

  公开（公告）日：2014-07-08
• Regioselective Synthesis of α-Methyl 2-Methyleneglutarate via a Novel Lactonization−Elimination Rearrangement
  作者：David M. Bartley、James K. Coward

  DOI：10.1021/jo051854a

  日期：2006.1.1

  A facile route to the alpha-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of O-silyl 2-(hydroxy-methyl)dimethylglutarate.