(R)-(+)-2-methyl-2,3-dihydrobenzo[b]thiophene | 129388-08-5

• 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)-(+)-2-methyl-2,3-dihydrobenzo[b]thiophene
• 英文别名: (2R)-2-methyl-2,3-dihydro-1-benzothiophene
• CAS: 129388-08-5
• 化学式: C₉H₁₀S
• 分子量: 150.244
• InChiKey: ZEAQOIXHQBWPOW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基苯并噻吩 在 C₅₄H₅₀N₄Ru 、 氢气 作用下， 以 正己烷 为溶剂， 25.0 ℃ 、9.0 MPa 条件下， 反应 24.0h， 以98%的产率得到(R)-(+)-2-methyl-2,3-dihydrobenzo[b]thiophene
  参考文献：
  名称：

  A Cyclometalated Ruthenium-NHC Precatalyst for the Asymmetric Hydrogenation of (Hetero)arenes and Its Activation Pathway

  摘要：

  This study describes the structural investigation of a highly versatile ruthenium-NHC (N-heterocyclic carbene) catalyst complex, which has been established for the asymmetric hydrogenation of various aromatic compounds. A complex containing an unusual doubly deprotonated NHC ligand was isolated and identified as the precatalyst to this complex. When its subsequent reactivity was monitored, two additional precatalysts, featuring partially hydrogenated naphthyl substituents, were characterized spectroscopically. Ligand hydrogenation appears to be a key activation process en route to the active catalyst.

  DOI：

  10.1021/acs.organomet.6b00702

文献信息

• Asymmetric Hydrogenation of Thiophenes and Benzothiophenes
  作者：Slawomir Urban、Bernhard Beiring、Nuria Ortega、Daniel Paul、Frank Glorius

  DOI：10.1021/ja306622y

  日期：2012.9.19

  An efficient and highly asymmetric ruthenium-N-heterocyclic carbene-catalyzed hydrogenation of substituted thiophenes and benzothiophenes is described, providing a new strategy for the formation of valuable enantiomerically pure tetrahydrothiophenes and 2,3-dihydrobenzothiophenes.
• A Cyclometalated Ruthenium-NHC Precatalyst for the Asymmetric Hydrogenation of (Hetero)arenes and Its Activation Pathway
  作者：Daniel Paul、Bernhard Beiring、Markus Plois、Nuria Ortega、Slawomir Kock、Danny Schlüns、Johannes Neugebauer、Robert Wolf、Frank Glorius

  DOI：10.1021/acs.organomet.6b00702

  日期：2016.10.24

  This study describes the structural investigation of a highly versatile ruthenium-NHC (N-heterocyclic carbene) catalyst complex, which has been established for the asymmetric hydrogenation of various aromatic compounds. A complex containing an unusual doubly deprotonated NHC ligand was isolated and identified as the precatalyst to this complex. When its subsequent reactivity was monitored, two additional precatalysts, featuring partially hydrogenated naphthyl substituents, were characterized spectroscopically. Ligand hydrogenation appears to be a key activation process en route to the active catalyst.