O-methyloctanaldoxime | 134023-68-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O-methyloctanaldoxime
• 英文别名: octanal O-methyl-oxime；N-methoxyoctan-1-imine
• CAS: 134023-68-0
• 化学式: C₉H₁₉NO
• 分子量: 157.256
• InChiKey: MNPSWFBVAFHEKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-methyloctanaldoxime 在 platinum(IV) oxide 氢气 、 四乙基对甲苯磺酸铵 作用下， 以 甲醇 、 异丙醇 为溶剂， 25.0 ℃ 、98.06 kPa 条件下， 反应 14.0h， 生成 1-(1-Amino-octyl)-cyclohexanol
  参考文献：
  名称：

  酮与O-甲基肟的电还原分子间偶联。合成2-氨基醇的便捷途径

  摘要：

  酮与O-甲基肟的电还原得到分子间偶联的产物2-甲氧基氨基醇，该产物容易还原为2-氨基醇。

  DOI：

  10.1016/s0040-4039(00)79486-x
• 作为产物：
  描述：

  octanal oxime 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 O-methyloctanaldoxime
  参考文献：
  名称：

  Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol

  摘要：

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.

  DOI：

  10.1021/jo00086a023

文献信息

• Pentafluorophenylammonium Trifluoromethanesulfonimide: Mild, Powerful, and Robust Catalyst for Mukaiyama Aldol and Mannich Reactions between Ketene Silyl Acetals and Ketones or Oxime Ethers
  作者：Ryohei Nagase、Jun Osada、Hiroaki Tamagaki、Yoo Tanabe

  DOI：10.1002/adsc.200900869

  日期：——

  (C6F5N+H3⋅NTf2−) promotes Mukaiyama aldol and Mannich reactions using ketene silyl acetals with ketones and oxime ethers, respectively. The present robust method is mild, but powerful enough to utilize less accessible electrophiles such as enolizable ketones and oxime ethers to produce a variety of β‐hydroxy esters and β‐alkoxyamino esters, respectively. Mechanistic investigation revealed in situ generation

  Pentafluorophenylammonium三氟甲磺酰亚胺（C 6 ˚F 5 Ñ + ħ 3 ⋅NTf 2 - ）促进向山羟醛和使用甲硅烷基烯酮缩醛与酮和肟醚，分别曼尼希反应。目前的稳健方法虽然温和，但功能强大，足以利用较难接近的亲电子试剂（例如可烯化的酮和肟醚）分别生产各种β-羟基酯和β-烷氧基氨基酯。机理研究表明，真正的活性催化剂原位生成了三甲基甲硅烷基双硫酰亚胺[Tf 2 N（TMS）]，并通过合理的1 H NMR测量得到了证实。
• Electroreductive intermolecular coupling of ketones with O-methyl oximes. A convenient route to synthesis of 2-amino alcohols
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto

  DOI：10.1016/s0040-4039(00)79486-x

  日期：1991.1

  The electroreduction of ketones together with O-methyl oximes gave intermolecularly coupled products, 2-methoxyamino alcohols, which were easily reduced to 2-amino alcohols.

  酮与O-甲基肟的电还原得到分子间偶联的产物2-甲氧基氨基醇，该产物容易还原为2-氨基醇。
• Ti-mediated direct and highly stereoselective Mannich reactions between esters and oximeethers
  作者：Takashi Funatomi、Shogo Nakazawa、Kunshi Matsumoto、Ryohei Nagase、Yoo Tanabe

  DOI：10.1039/b717318k

  日期：——

  The first general method of direct and highly stereoselective Ti-mediated Mannich reaction between three types of simpleesters and E and Z mixtures of oxime ethers (aliphatic and aromatic) is accomplished.

  实现了三种类型的单酯与肟醚（脂肪族和芳香族）的E和Z混合物之间直接和高度立体选择性的Ti介导的Mannich反应的第一种一般方法。
• Reduction of oximes, oxime ethers, and oxime esters with diborane. Novel synthesis of amines
  作者：Henry Feuer、D. M. Braunstein

  DOI：10.1021/jo01258a062

  日期：1969.6
• Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Ayuko Yamanami、Ryoji Nomura

  DOI：10.1021/jo00086a023

  日期：1994.4

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.