3-phenylpropanal O-methyl oxime | 69163-87-7

• 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-phenylpropanal O-methyl oxime
• 英文别名: dihydrocinnamaldehyde oxime O-methyl ether；3-Phenyl-propionaldehyde O-methyl-oxime；N-methoxy-3-phenylpropan-1-imine
• CAS: 69163-87-7
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: BGODCHQCEPMQOX-UHFFFAOYSA-N

物化性质

• 沸点：
  248.3±33.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-溴代异丁酸甲酯 、 3-phenylpropanal O-methyl oxime 在 四氯化钛 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到methyl 2,2-dimethyl-3-(methoxyamino)-5-phenylpentanoate
  参考文献：
  名称：

  酯和肟醚之间的钛介导的直接和高度立体选择性曼尼希反应。

  摘要：

  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。

  DOI：

  10.1039/b717318k
• 作为产物：
  描述：

  (NE)-N-(3-苯基亚丙基)羟胺 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-phenylpropanal O-methyl oxime
  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。
• 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。
• Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines
  作者：Cecilia M. Hendy、Cameron J. Pratt、Nathan T. Jui、Simon B. Blakey

  DOI：10.1021/acs.orglett.3c00126

  日期：2023.3.10

  Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived N,N-dialkylhydrazones and trifluoromethylarenes (CF3-arenes). This method relies on selective C–F bond cleavage via reduction of the CF3-arene. We show that a diverse set of CF3-arenes and CF3-heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic

  在这里，我们报告了一种从简单的醛衍生N,N -二烷基腙和三氟甲基芳烃 (CF 3 -芳烃)形成二氟化芳基乙胺的有效模块化方法。该方法依赖于通过 CF 3 -芳烃的还原选择性 C-F 键断裂。我们表明，一组不同的 CF 3 -芳烃和 CF 3 -杂芳烃与一系列芳基和烷基腙顺利反应。β-二氟苄基肼产物可以选择性地裂解形成相应的苄基二氟芳基乙胺。
• 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.