3-hydroxyanilino-2-butanone | 682746-17-4

• 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: 3-hydroxyanilino-2-butanone
• 英文别名: 3-[Hydroxy(phenyl)amino]butan-2-one；3-(N-hydroxyanilino)butan-2-one
• CAS: 682746-17-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: UFBXZDVVIUYUBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  亚硝基苯 、 丁酮 在 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以40%的产率得到(3R)-3-(N-phenylaminooxy)butane-2-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

• Process of making alpha-aminooxyketone/alpha-aminooxyaldehyde and alpha-hydroxyketone/alpha-hydroxyaldehyde compounds and a process making reaction products from cyclic alpha,beta-unsaturated ketone substrates and nitroso substrates
  申请人：Momiyama Norie

  公开号：US20070037973A1

  公开（公告）日：2007-02-15

  The present invention is directed to a process of making α-aminooxyketone and α-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X a —X c represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic α,β-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,β-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

  本发明涉及一种制备α-氨氧基酮和α-羟基酮化合物的方法。合成途径通常涉及在催化剂存在下反应醛或酮底物和亚硝基底物，所述催化剂的公式为（IV）：其中Xa-Xc分别独立表示氮、碳、氧或硫，Z表示具有或不具有取代基的4到10个成员环，并可选择进一步步骤将形成的α-氨氧基酮化合物转化为α-羟基酮化合物。本发明的结果是具有高对映选择性和高纯度的α-氨氧基酮和α-羟基酮化合物。本发明还涉及一种催化不对称O-亚硝基Aldol/Michael反应。该反应的底物通常为环状α,β-不饱和酮底物和亚硝基底物。该方法通常涉及在脯氨酸基催化剂存在下反应环状α,β-不饱和酮底物和亚硝基底物，以提供杂环产物。
• PROCESS OF MAKING ALPHA-AMINOOXYKETONE/ALPHA-AMINOOXYALDEHYDE AND ALPHA-HYDROXYKETONE/ALPHA-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS MAKING REACTION PRODUCTS FROM CYCLIC ALPHA, BETA-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES
  申请人：Momiyama Norie

  公开号：US20100099915A1

  公开（公告）日：2010-04-22

  The present invention is directed to a process of making α-aminooxyketone and α-hydroxyketone compounds. The synthetic pathway generally involves reacting an aldehyde or ketone substrate and a nitroso substrate in the presence of a catalyst of the formula (IV): wherein X a —X c represent independently nitrogen, carbon, oxygen or sulfur and Z represents a 4 to 10-membered ring with or without a substituent and optionally a further step to convert the α-aminooxyketone compound formed to the α-hydroxyketone compound. The present invention results in α-aminooxyketone and α-hydroxyketone compounds with high enantioselectivity and high purity. The present invention is also directed to a catalytic asymmetric O-nitroso Aldol/Michael reaction. The substrates of this reaction are generally cyclic α,β-unsaturated ketone substrate and a nitroso substrate. This methodology generally involves reacting the cyclic α,β-unsaturated ketone substrate and the nitroso substrate in the presence of a proline-based catalyst, to provide a heterocyclic product.

  本发明涉及一种制备α-氨氧酮和α-羟基酮化合物的过程。合成路径通常涉及在催化剂的存在下反应醛或酮底物和亚硝基底物，催化剂的公式为（IV）：其中Xa-Xc代表独立的氮、碳、氧或硫，Z代表具有或不具有取代基的4到10个成员环，并可选择进一步步骤将形成的α-氨氧酮化合物转化为α-羟基酮化合物。本发明产生了具有高对映选择性和高纯度的α-氨氧酮和α-羟基酮化合物。本发明还涉及一种催化不对称O-亚硝基Aldol/Michael反应。该反应的底物通常是环状α，β-不饱和酮底物和亚硝基底物。该方法通常涉及在脯氨酸基催化剂的存在下反应环状α，β-不饱和酮底物和亚硝基底物，以提供杂环产物。
• PROCESS OF MAKING ALFA-AMINOOXYKETONE/ ALFA-AMINOOXYALDEHYDE AND ALFA-HYDROXYKETONE/ ALFA-HYDROXYALDEHYDE COMPOUNDS AND A PROCESS OF MAKING REACTION PRODUCTS FROM CYCLIC ALFA, BETA-UNSATURATED KETONE SUBSTRATES AND NITROSO SUBSTRATES
  申请人：Japan Science and Technology Agency

  公开号：EP1742905A2

  公开（公告）日：2007-01-17
• US7872123B2
  申请人：——

  公开号：US7872123B2

  公开（公告）日：2011-01-18
• US8252941B2
  申请人：——

  公开号：US8252941B2

  公开（公告）日：2012-08-28