4-methoxyoctan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyoctan-2-one
• 英文别名: 4-methoxy-2-octanone
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: AUMNRLNCQPDYIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 4-methoxyoctan-2-one 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 生成 4-methoxy-2-methyl-2-octanol
  参考文献：
  名称：

  Copper-Catalyzed Remote sp³ C−H Chlorination of Alkyl Hydroperoxides

  摘要：

  A copper-catalyzed methodology to functionalize remote sp(3) C-H bonds in alkyl hydroperoxides is presented. The atom-transfer chlorination utilizes simple ammonium chloride salts as the chlorine source, and the internal redox process requires no external redox reagents.

  DOI：

  10.1021/ol100472t
• 作为产物：
  描述：

  2-(三甲基硅氧基)丙烯 、 1,1-二甲氧基戊烷 在 [Ir(cod)(PPh₃)2]OTf 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到4-methoxyoctan-2-one
  参考文献：
  名称：

  Iridium-catalyzed crossed aldol coupling and a new concept to form an Ir–Si species

  摘要：

  [Ir(COD)(PPh3)(2)]X (X=PF6, ClO4, and OTf) activated by H-2 molecule catalyzes Mukaiyama-type aldol coupling between enoxysilanes and acetals or aldehydes. An Ir-Si species formed in the first stage of the catalytic cycle plays an important role in these reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02303-5

文献信息

• Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
  作者：Zachary K. Wickens、Kacper Skakuj、Bill Morandi、Robert H. Grubbs

  DOI：10.1021/ja411749k

  日期：2014.1.22

  The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical

  在烯丙基和高烯丙基位置带有不同氧基团的烯烃的醛选择性氧化是通过亚硝酸盐改性的瓦克氧化完成的。容易获得的含氧烯烃以高达 88% 的醛收率和高达 97% 的醛选择性被氧化。醛选择性氧化能够快速、对映选择性地合成一种重要的药剂托莫西汀。最后，探讨了近端官能团对这种反马尔科夫尼科夫反应的影响，提供了重要的初步机制见解。
• Direct organocatalytic hydroalkoxylation of α,β-unsaturated ketones
  作者：Dhevalapally B. Ramachary、Rumpa Mondal

  DOI：10.1016/j.tetlet.2006.08.134

  日期：2006.10

  The direct addition of a variety of alcohols to in situ activated olefins was observed in the presence of mild bifunctional amine/acid catalysts. Unlike existing methods, the reactions proceed at room temperature and in the absence of transition metals. The use of simple commercially available catalysts, amines and acids makes this an attractive method for the preparation of beta-alkoxy ketones, which are prevalent targets and intermediates in organic synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Remote sp³ C−H Chlorination of Alkyl Hydroperoxides
  作者：Rituparna Kundu、Zachary T. Ball

  DOI：10.1021/ol100472t

  日期：2010.6.4

  A copper-catalyzed methodology to functionalize remote sp(3) C-H bonds in alkyl hydroperoxides is presented. The atom-transfer chlorination utilizes simple ammonium chloride salts as the chlorine source, and the internal redox process requires no external redox reagents.
• Iridium-catalyzed crossed aldol coupling and a new concept to form an Ir–Si species
  作者：Isamu Matsuda、Yuki Hasegawa、Tatsuya Makino、Kenji Itoh

  DOI：10.1016/s0040-4039(99)02303-5

  日期：2000.2

  [Ir(COD)(PPh3)(2)]X (X=PF6, ClO4, and OTf) activated by H-2 molecule catalyzes Mukaiyama-type aldol coupling between enoxysilanes and acetals or aldehydes. An Ir-Si species formed in the first stage of the catalytic cycle plays an important role in these reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.