(R)-(-)-1,3-diethyl-5-(1-phenylethyl)benzene | 1418308-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(-)-1,3-diethyl-5-(1-phenylethyl)benzene
• 英文别名: 1,3-dimethoxy-5-(1-phenylethyl)benzene；1,3-dimethoxy-5-[(1R)-1-phenylethyl]benzene
• CAS: 1418308-77-6
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: QTWRMQWCTUVSJO-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 盐酸 、 C₃₀H₃₇IrN₂O₃P⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 17.17h， 生成 (S)-(-)-1,3-diethyl-5-(1-phenylethyl)benzene 、 (R)-(-)-1,3-diethyl-5-(1-phenylethyl)benzene
  参考文献：
  名称：

  Distinctive Meta-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation

  摘要：

  An iridium-catalyzed asymmetric hydrogenation of 1,1-diarylkenes is described. Employing a novel, modular phosphoramidite ligand, PhosPrOx, in this transformation affords biologically relevant 1,1-diarylmethine products in good enantiomeric ratios (96.5:3.5 to 71:29). We propose that a meta-directing group, 3,5-dimethoxyphenyl, is responsible for the observed enantioselection, the highest reported, to date, for iridium-catalyzed hydrogenation of 1,1-diarylalkenes lacking ortho-directing groups.

  DOI：

  10.1021/ol303465c

文献信息

• Chiral Iridium Complexes of Anionic NCP Pincer Ligand for Asymmetric Transfer Hydrogenation of 1,1-Diarylethenes with Ethanol
  作者：Lu Qian、Xixia Tang、Zhidao Huang、Yulei Wang、Guixia Liu、Zheng Huang

  DOI：10.1021/acs.orglett.1c03455

  日期：2021.11.19

  Chiral iridium complexes ligated by anionic oxazoline-bearing NCP-type pincer ligands were developed and applied to the asymmetric transfer hydrogenation (ATH) of diarylethenes using environmentally benign ethanol as the hydrogen donor. High enantioselectivities could be achieved for substrates bearing ortho-Me, ortho-Cl, or ortho-Br substituents on one of the aryl groups. The ATH of ortho-Br-substituted

  开发了由带有阴离子恶唑啉的 NCP 型钳形配体连接的手性铱配合物，并将其应用于使用环境友好型乙醇作为氢供体的二芳基乙烯的不对称转移氢化 (ATH)。对于在芳基之一上带有邻-Me、邻-Cl或邻-Br取代基的底物可以实现高对映选择性。由于 C （芳基） -Br 键易于经历各种新的键形成事件，邻位-Br 取代的二芳基乙烯的 ATH特别有吸引力。
• Distinctive <i>Meta</i>-Directing Group Effect for Iridium-Catalyzed 1,1-Diarylalkene Enantioselective Hydrogenation
  作者：Elizabeth N. Bess、Matthew S. Sigman

  DOI：10.1021/ol303465c

  日期：2013.2.1

  An iridium-catalyzed asymmetric hydrogenation of 1,1-diarylkenes is described. Employing a novel, modular phosphoramidite ligand, PhosPrOx, in this transformation affords biologically relevant 1,1-diarylmethine products in good enantiomeric ratios (96.5:3.5 to 71:29). We propose that a meta-directing group, 3,5-dimethoxyphenyl, is responsible for the observed enantioselection, the highest reported, to date, for iridium-catalyzed hydrogenation of 1,1-diarylalkenes lacking ortho-directing groups.