2-methoxybenzaldehyde O-methyloxime | 107369-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methoxybenzaldehyde O-methyloxime
• 英文别名: 2-Methoxybenzaldehyd-methoxim；2-Methoxy-benzaldehyd-(O-methyl-oxim)；N-methoxy-1-(2-methoxyphenyl)methanimine
• CAS: 107369-63-1
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: OZFFQDGZYYUZJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  241 °C(Press: 761 Torr)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxybenzaldehyde O-methyloxime 生成 邻甲氧基苯甲醛
  参考文献：
  名称：

  Irvine; Moody, Journal of the Chemical Society, 1908, vol. 93, p. 102

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-羟基苯甲醛肟 、 碘甲烷 在 sodium ethanolate 作用下， 生成 2-methoxybenzaldehyde O-methyloxime
  参考文献：
  名称：

  Lach, Chemische Berichte, 1883, vol. 16, p. 1786

  摘要：

  DOI：

文献信息

• Reaction of aldehyde O-alkyl oxime with organometallic compounds
  作者：Shinichi Itsuno、Koji Miyazaki、Koichi Ito

  DOI：10.1016/s0040-4039(00)84709-7

  日期：1986.1

  Aldehyde O-alkyl oximes were converted into ketones with high yields when they were treated with alkyllithium compounds or Grignard reagents followed by hydrolysis. Amines as reductive alkylation products of aldehyde O-alkyl oximes were also obtained by BH3 reduction before hydrolysis.

  当用烷基锂化合物或格利雅试剂进行处理，然后水解时，醛O-烷基肟被高产率地转化为酮。还通过在水解前通过BH 3还原获得作为醛基O-烷基肟的还原烷基化产物的胺。
• Palladium-Catalyzed Direct Acylation of Ketoximes and Aldoximes from the Alcohol Oxidation Level through C-H Bond Activation
  作者：Satyasheel Sharma、Minyoung Kim、Jihye Park、Mirim Kim、Jong Hwan Kwak、Young Hoon Jung、Joa Sub Oh、Youngil Lee、In Su Kim

  DOI：10.1002/ejoc.201300649

  日期：2013.10

  A highly efficient palladium-catalyzed oxidative ortho-acylation of O-methyl ketoximes and O-methyl aldoximes with benzylic and aliphatic alcohols from the alcohol oxidation level is described. This protocol potentially provides new opportunities to use readily available alcohols as starting materials for catalytic reactions, and represents a catalytic alternative to transcend the barriers imposed

  描述了一种高效的钯催化氧化邻位酰化 O-甲基酮肟和 O-甲基醛肟与苯甲醇和脂肪醇从醇氧化水平。该协议可能为使用现成的醇作为催化反应的起始材料提供了新的机会，并代表了一种催化替代方案，可以超越经典的弗里德尔-克拉夫茨酰化所施加的障碍。
• Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals
  作者：Rino Leardini、Hamish McNab、Matteo Minozzi、Daniele Nanni、David Reed、Andrew G. Wright

  DOI：10.1039/b103181n

  日期：2001.10.11

  Genereration of the iminyls 1d and 1e by standard methods in the gas-phase by flash vacuum pyrolysis (FVP), or in solution, respectively, gives rise to 1,3-benzoxazines 18 and 22 by a mechanism which probably involves a 1,6-hydrogen atom translocation. Under FVP conditions, 2-cyanophenol 14 is a major product from 2-alkoxyphenylalkaniminyls 1b–d; the dealkylation is an integral part of the reaction

  通过闪蒸真空热解（FVP）在气相中或在溶液中通过标准方法分别生成亚胺基1d和1e可能通过涉及1,6的机理生成1,3-苯并恶嗪18和22。 -氢原子易位。在FVP条件下，2-氰基苯酚14是2-烷氧基苯基烷胺基1b–d的主要产物；脱烷基反应是反应机理不可或缺的部分，而不是随后的2-烷氧基苄腈的反应，而2-烷氧基苄腈本身只是热解的极少产物。
• Novel One-Pot Synthesis of <i>N</i>-Alkyl Arylamines from Oxime Ethers Using Organometallic Reagents
  作者：Takeaki Naito、Partha Mukhopadhyay、Okiko Miyata

  DOI：10.1055/s-2007-980358

  日期：2007.6

  α-disubstituted secondary arylamines from oxime ethers has been developed by two separate additions of organometallic reagents. As a related arylamine construction, very efficient synthesis of N-(diallyl)methyl arylamines is achieved via domino reactions involving addition-eliminative re-arrangement-addition reactions of acyclic and cyclic oxime ethers with allylmagnesium bromide.

  通过两次单独添加有机金属试剂，开发了一种从肟醚中合成 α,α-二取代仲芳胺的新型一锅法。作为相关的芳胺结构，N-(二烯丙基)甲基芳胺的非常有效的合成是通过多米诺反应实现的，该反应涉及无环和环状肟醚与烯丙基溴化镁的加成-消除重排-加成反应。
• Chirality Transfer in Rhodium(I)-Catalyzed [3 + 2]-Cycloaddition of Vinyl Aziridines and Oxime Ethers: Atom-Economical Synthesis of Chiral Imidazolidines
  作者：Tao-Yan Lin、Hai-Hong Wu、Jian-Jun Feng、Junliang Zhang

  DOI：10.1021/acs.orglett.8b01378

  日期：2018.6.15

  A highly efficient and stereoselective synthesis of enantioenriched imidazolidines by rhodium-catalyzed intermolecular [3 + 2] cycloaddition reaction of chiral vinyl aziridines and oxime ethers has been successfully developed. Notably, both aldoximes and ketoximes are suitable substrates to afford the corresponding chiral imidazolidines in high yields with good stereoselectivity. This transformation

  通过铑催化的手性乙烯基氮丙啶和肟醚的分子间[3 + 2]环加成反应，已成功开发了对映体富集的咪唑烷的高效立体选择性合成。值得注意的是，醛肟和酮肟都是合适的底物，以高收率和良好的立体选择性提供相应的手性咪唑烷。这种转化代表了一个空前的例子，该例子在乙烯基氮丙啶的环加成中利用酮亚胺衍生物作为氮杂[2C]组分。