(3-Methoxyphenyl)(o-tolyl)methanol | 944672-22-4

• 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: (3-Methoxyphenyl)(o-tolyl)methanol
• 英文别名: (3-methoxyphenyl)-(2-methylphenyl)methanol
• CAS: 944672-22-4
• 化学式: C₁₅H₁₆O₂
• mdl: MFCD11097988
• 分子量: 228.291
• InChiKey: HHCJCEXNVQZADL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-Methoxyphenyl)(o-tolyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 (3-甲氧基苯基)(2-甲基苯基)甲酮
  参考文献：
  名称：

  钴催化的1,1-二芳烃的不对称加氢

  摘要：

  通过使用稳定的手性恶唑啉亚氨基吡啶-钴络合物作为前催化剂，开发了对映体选择性高的钴催化的1,1-二芳烃的氢化反应。观察到独特的邻氯化物效应实现了高对映选择性。易于除去以及氯基团的进一步转化使该方案成为合成各种手性1,1-二芳基乙烷的潜在有用替代品。此过程可以在室温下1克大气压的氢气中以克为单位成功进行。

  DOI：

  10.1021/acs.orglett.6b00453
• 作为产物：
  描述：

  2-溴甲苯 、 3-甲氧基苯甲醛 在 1,10-菲罗啉 、 3-氯丙烯 、 三氟乙酸 、 cobalt(II) bromide 、 锌 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以82%的产率得到(3-Methoxyphenyl)(o-tolyl)methanol
  参考文献：
  名称：

  CoI催化的芳香卤化物与芳香醛和亚胺的Barbier反应

  摘要：

  使用CoBr 2 / 1,10-菲咯啉催化体系和超过化学计量的锌可以实现芳香族卤化物和亲电试剂的还原Barbier偶联。该反应显示出广泛的底物范围，包括（杂）芳基氯化物作为亲核试剂和醛或亚胺类作为亲电试剂，分别导致了中等至极好的收率的二芳基甲醇和二芳基甲胺。

  DOI：

  10.1002/chem.201806239

文献信息

• Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes
  作者：Jianhui Chen、Chenhui Chen、Chonglei Ji、Zhan Lu

  DOI：10.1021/acs.orglett.6b00453

  日期：2016.4.1

  Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine–cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral

  通过使用稳定的手性恶唑啉亚氨基吡啶-钴络合物作为前催化剂，开发了对映体选择性高的钴催化的1,1-二芳烃的氢化反应。观察到独特的邻氯化物效应实现了高对映选择性。易于除去以及氯基团的进一步转化使该方案成为合成各种手性1,1-二芳基乙烷的潜在有用替代品。此过程可以在室温下1克大气压的氢气中以克为单位成功进行。
• Na-promoted aerobic oxidation of alcohols to ketones
  作者：Li-Hong Zhou、Xiao-Qi Yu、Lin Pu

  DOI：10.1016/j.tetlet.2009.11.079

  日期：2010.1

  Aerobic oxidation of a number of diaryl and arylalkyl carbinols to ketones was promoted by Na in THF at room temperature with up to 99% yield. This new oxidation method is also selective with good efficiency for the oxidation of benzylic secondary alcohols but not for a primary alcohol or nonbenzylic secondary alcohols. Under nitrogen, a catalytic amount of Ni or transition metal halides such as COCl3, FeCl3, and NiCl3 in combination with Na was also found to conduct a dehydrogenation of a secondary alcohol to the corresponding ketone in high yield at room temperature. (C) 2009 Elsevier Ltd. All rights reserved.
• A chiral Rh–phosphite complex displaying high activity in the enantioselective Rh-catalyzed addition of arylboronic acids to carbonyl compounds: when and why atropos is better than tropos
  作者：Varsha R. Jumde、Sarah Facchetti、Anna Iuliano

  DOI：10.1016/j.tetasy.2010.11.009

  日期：2010.12

  The use of deoxycholic acid derived tropos and atropoisomeric phosphites as chiral ligands in the Rh-catalyzed enantioselective addition of arylboronic acids to arylaldehydes and 2,2,2-trifluoroacetophenone is presented. Screening of these phosphites showed the high activity of the Rh-complex obtained starting from one of the two atropoisomeric ligands, which afforded complete conversion of the carbonyl compounds in short reaction times under mild reaction conditions and with ee's of up to 84%. A study aimed at getting information about the different behavior of tropos and atropoisomeric ligands is also reported. (C) 2010 Elsevier Ltd. All rights reserved.
• Co ^I ‐Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines
  作者：Marc Presset、Jérôme Paul、Ghania Nait Cherif、Nisanthan Ratnam、Nicolas Laloi、Eric Léonel、Corinne Gosmini、Erwan Le Gall

  DOI：10.1002/chem.201806239

  日期：2019.3.21

  The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr2/1,10‐phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro‐nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent

  使用CoBr 2 / 1,10-菲咯啉催化体系和超过化学计量的锌可以实现芳香族卤化物和亲电试剂的还原Barbier偶联。该反应显示出广泛的底物范围，包括（杂）芳基氯化物作为亲核试剂和醛或亚胺类作为亲电试剂，分别导致了中等至极好的收率的二芳基甲醇和二芳基甲胺。
• Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation
  作者：Jiayu Zhou、Jianxun Ye、Yang Zhang、Zhaodi Li、Jingjing Li、Delong Liu、Wanbin Zhang

  DOI：10.1002/adsc.202300213

  日期：——

  The RuPHOX-Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram-scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, (S)-Orphenadrine

  已经建立了 RuPHOX-Ru 催化的二芳基酮不对称氢化，以高达 99% 的产率和 99% ee 提供相应的手性二芳基甲醇。该方案可以在催化剂负载量相对较低 (2000 S/C) 的克规模上进行，所得产品可进行多种有用的转化，特别是用于手性药物的合成，例如 ( S ) -Orphenadrine和( S )-新苯二甲酸。氘标记和对照实验表明，RuPHOX-Ru 催化的不对称氢化完全以 H 2作为唯一氢源进行氢化。