3-(甲氧基亚氨基)-3-苯基丙酸乙酯 | 342626-64-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-(甲氧基亚氨基)-3-苯基丙酸乙酯
• 英文名称: Ethyl 3-phenyl-3-methoxyliminopropionat
• 英文别名: ethyl 3-(methoxyimino)-3-phenylpropanoate；Ethyl 3-methoxyimino-3-phenylpropanoate；ethyl 3-methoxyimino-3-phenylpropanoate
• CAS: 342626-64-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: YQHZUTCZXGSEFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(甲氧基亚氨基)-3-苯基丙酸乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以90%的产率得到(Z)-ethyl 2-diazo-3-(methoxyimino)-3-phenylpropanoate
  参考文献：
  名称：

  2-烷基/芳氧基-2H-叠氮基的简便合成及其在吡咯合成中的应用。

  摘要：

  由α-重氮肟醚通过光解生成的游离碳烯容易插入NO，以良好或极好的收率得到2-烷基/芳氧基-2H-叠氮基。该方法允许通过1，3-偶极环加成反应发展用于吡咯合成的串联反应。

  DOI：

  10.1039/c2cc30490b

文献信息

• Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers
  作者：Sangjune Park、Hyunseok Kim、Jeong-Yu Son、Kyusik Um、Sooho Lee、Yonghyeon Baek、Boram Seo、Phil Ho Lee

  DOI：10.1021/acs.joc.7b01714

  日期：2017.10.6

  The Cu-catalyzed, formal aza-[3 + 2] cycloaddition reaction of pyridine derivatives with α-diazo oxime ethers in trifluoroethanol was used to synthesize imidazopyridines via the release of molecular nitrogen and elimination of alcohol. These methods enabled modular synthesis of a wide range of N-heterobicyclic compounds such as imidazopyridazines, imidazopyrimidines, and imidazopyrazines with an α-imino

  吡啶衍生物与α-重氮肟醚在三氟乙醇中的Cu催化的正式aza- [3 + 2]环加成反应用于通过释放分子氮和消除醇来合成咪唑并吡啶。这些方法能够与由α-重氮肟醚和铜生成的α-亚氨基Cu-类胡萝卜素模块化合成多种N-杂环双环化合物，例如咪唑并哒嗪，咪唑并嘧啶和咪唑并吡嗪。
• Ruthenium(II)-Catalyzed C−H Difluoromethylation of Ketoximes: Tuning the Regioselectivity from the <i>meta</i> to the <i>para</i> Position
  作者：Chunchen Yuan、Lei Zhu、Runsheng Zeng、Yu Lan、Yingsheng Zhao

  DOI：10.1002/anie.201711221

  日期：2018.1.26

  A highly para‐selective CAr−H difluoromethylation of ketoxime ethers under ruthenium catalysis has been developed. A wide variety of ketoxime ethers are compatible with the reaction, which leads to the corresponding para‐difluoromethylated products in moderate to good yield. A mechanistic study clearly showed that chelation‐assisted cycloruthenation is the key factor in the para selectivity of the

  已经开发了在钌催化下酮肟醚的高度对位选择性C Ar -H二氟甲基化。各种各样的酮肟醚均可与该反应相容，从而以中等至良好的产率产生相应的对二氟甲基化产物。一项机理研究清楚地表明，螯合辅助的环化钌是影响酮肟醚二氟甲基化对位选择性的关键因素。使用密度泛函理论来获得对位选择性的理论理解。＃
• Facile synthesis of 2-alkyl/aryloxy-2H-azirines and their application in the synthesis of pyrroles
  作者：Xinxin Qi、Xianxiu Xu、Cheol-Min Park

  DOI：10.1039/c2cc30490b

  日期：——

  Free carbenes generated from alpha-diazo oxime ethers by photolysis undergo facile N-O insertion to afford 2-alkyl/aryloxy-2H-azirines in good to excellent yields. This method allowed for the development of a tandem reaction for pyrrole synthesis via 1,3-dipolar cycloaddition.

  由α-重氮肟醚通过光解生成的游离碳烯容易插入NO，以良好或极好的收率得到2-烷基/芳氧基-2H-叠氮基。该方法允许通过1，3-偶极环加成反应发展用于吡咯合成的串联反应。
• Development of a Commercial Process for (<i>S</i>)-β-Phenylalanine
  作者：J. Ian Grayson、Jürgen Roos、Steffen Osswald

  DOI：10.1021/op200084g

  日期：2011.9.16

  The development of a commercial manufacturing route for (S)-beta-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale
• NaOH/Et₃N-Promoted Stereoselective One-Pot Synthesis of<i>α</i>-Diazo Oxime Ethers via Diazo Transfer Reaction
  作者：Bharath Kumar Kuruba、Nusrathulla Shariff、Samuel Vasanthkumar、Lourdusamy Emmanuvel

  DOI：10.1080/00397911.2015.1085575

  日期：2015.11.2

  Abstract For the first time, we have observed a combined effect of two bases NaOH/Et3N to promote the diazo transfer reaction of β-oximino esters. This unusual synergistic effect has been employed to obtain α-diazo oxime ethers directly from β-keto esters by one-pot process. This method is simple and cost-effective and the reagents are readily available. GRAPHICAL ABSTRACT

  摘要 我们首次观察到两种碱NaOH/Et3N的联合作用促进β-肟基酯的重氮转移反应。这种不寻常的协同效应已被用于通过一锅法直接从 β-酮酯获得 α-重氮肟醚。该方法简单经济，试剂易得。图形概要