(R)-3-(N-phenyl-aminooxy)-1-methylpiperidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: (R)-3-(N-phenyl-aminooxy)-1-methylpiperidin-4-one
• 英文别名: (R)-3-anilinoxy-1-methylpiperidin-4-one；(R)-3-anilinooxy-1-methylpiperidin-4-one；(R)-3-anilinooxy-1-methylpiperidine-4-on；(3R)-3-anilinooxy-1-methylpiperidin-4-one
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: AYRGXMFXHQDLSW-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 亚硝基苯 在 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以44%的产率得到(R)-3-(N-phenyl-aminooxy)-1-methylpiperidin-4-one
  参考文献：
  名称：

  脯氨酸直接催化醛和酮的不对称α-氨氧化

  摘要：

  使用亚硝基苯作为氧源开发了脯氨酸直接催化的醛和酮的不对称α-氨基羟甲基化反应，提供了对映体选择性极好的α-苯胺基氧基-醛和-酮。已优化了反应条件，发现低温（-20°C）是醛成功进行α-氨氧基化的关键，而缓慢添加亚硝基苯对于酮是至关重要的。给出了反应范围。

  DOI：

  10.1021/jo049338s

文献信息

• OPTICALLY ACTIVE ALPHA-AMINOOXYKETONE DERIVATIVES AND PROCESS FOR PRODUCTION THEREOF
  申请人：Tokyo University of Science

  公开号：EP1661885A1

  公开（公告）日：2006-05-31

  The corresponding α-aminooxy ketone is manufactured with a high yield and a high enantioselectivity. A manufacturing method for an optically active α-aminooxy ketone derivative expressed by formula (1), wherein a ketone expressed by formula (2) is caused to react with a nitroso compound expressed by formula (3) in the presence of a proline derivative expressed by formula (4). In the formula, R1 and R2 respectively denote an alkyl, alkenyl or alkynyl group, and R1 and R2 may be linked to form a ring. R3 denotes an aryl, heterocyclic, alkyl, alkenyl or alkynyl group. A denotes a hydrogen atom, alkoxy group, aryloxy group, acyloxy group or silyloxy group which may have a substituent.

  相应的α-氨基酮的制造具有高产率和高对映选择性。一种具有光学活性的α-氨基酮衍生物的制造方法，其中式(1)表示的酮与式(3)表示的亚硝基化合物在式(4)表示的脯氨酸衍生物存在下发生反应。 式中，R1 和 R2 分别表示烷基、烯基或炔基，R1 和 R2 可连接成环。R3 表示芳基、杂环基、烷基、烯基或炔基。A 表示氢原子、烷氧基、芳氧基、酰氧基或硅氧基，可带有取代基。
• Highly Enantioselective α-Aminoxylation of Aldehydes and Ketones with a Polymer-Supported Organocatalyst
  作者：Daniel Font、Amaia Bastero、Sonia Sayalero、Ciril Jimeno、Miquel A. Pericàs

  DOI：10.1021/ol070526p

  日期：2007.5.1

  The first catalytic enantioselective alpha-aminoxylation of aldehydes and ketones using an insoluble, polymer-supported organocatalyst (1) derived from trans-4-hydroxyproline is reported (ee: 96-99%). Reaction rates in the aminoxylation of cyclic ketones with 1 are higher than those reported with L-proline. The insoluble nature of 1 simplifies workup conditions and allows catalyst recycling without an apparent decrease in enantioselectivity or yield.
• EP1661885
  申请人：——

  公开号：——

  公开（公告）日：——
• Direct Proline-Catalyzed Asymmetricα-Aminoxylation of Ketones
  作者：Yujiro Hayashi、Junichiro Yamaguchi、Tatsunobu Sumiya、Mitsuru Shoji

  DOI：10.1002/anie.200353085

  日期：2004.2.20
• Optically active alpha-aminooxyketone derivatives and process for production thereof
  申请人：Hayashi Yujiro

  公开号：US20060293525A1

  公开（公告）日：2006-12-28

  The corresponding α-aminooxy ketone is manufactured with a high yield and a high enantioselectivity. A manufacturing method for an optically active α-aminooxy ketone derivative expressed by formula (1), wherein a ketone expressed by formula (2) is caused to react with a nitroso compound expressed by formula (3) in the presence of a proline derivative expressed by formula (4). In the formula, R 1 and R 2 respectively denote an alkyl, alkenyl or alkynyl group, and R 1 and R 2 may be linked to form a ring. R 3 denotes an aryl, heterocyclic, alkyl, alkenyl or alkynyl group. A denotes a hydrogen atom, alkoxy group, aryloxy group, acyloxy group or silyloxy group which may have a substituent.