(R)-2-(N-phenyl-aminooxy)-pentan-1-ol

• 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)-2-(N-phenyl-aminooxy)-pentan-1-ol
• 英文别名: (R)-2-[N-(phenyl)aminoxy]pentan-1-ol；(R)-2-(N-phenylaminoxy)pentan-1-ol；(2R)-2-(N-anilinyloxy)pentan-1-ol；(R)-2-(phenylaminooxy)pentan-1-ol；(2R)-2-anilinoxypentanol；(R)-2-anilinoxypentanol；(2R)-2-anilinooxypentan-1-ol
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: WYFXQBZESYRHQN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-2-anilinoxypentanal 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 以46 mg的产率得到(R)-2-(N-phenyl-aminooxy)-pentan-1-ol
  参考文献：
  名称：

  Highly enantioselective l-thiaproline catalyzed α-aminoxylation of aldehydes in aqueous media

  摘要：

  在水和四丁基溴化铵存在下，开发出了高对映选择性的 L-硫代氨酸催化δ-氨氧基化醛，然后进行原位诱导，得到相应的δ-氨氧基醇，收率从好到高（74%-88%），对映选择性极佳（93%->99%）。

  DOI：

  10.1039/b817950f

文献信息

• Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline
  作者：Xacobe C Cambeiro、Rafael Martín-Rapún、Pedro O Miranda、Sonia Sayalero、Esther Alza、Patricia Llanes、Miquel A Pericàs

  DOI：10.3762/bjoc.7.172

  日期：——

  The application of polystyrene-immobilized proline-based catalysts in packed-bed reactors for the continuous-flow, direct, enantioselective α-aminoxylation of aldehydes is described. The system allows the easy preparation of a series of β-aminoxy alcohols (after a reductive workup) with excellent optical purity and with an effective catalyst loading of ca. 2.5% (four-fold reduction compared to the batch process) working at residence times of ca. 5 min.

  在填充床反应器中应用基于聚苯乙烯固定的脯氨酸催化剂，用于连续流动、直接、对映选择性α-氨氧基化醛类的方法。该系统可轻松制备一系列β-氨氧基醇（在还原处理后），具有优异的光学纯度，并且有效的催化剂负载约为2.5%（与批处理相比减少了四倍），在约0.5分钟的停留时间下运行。
• Imidazolium Ion-Tagged Proline Organocatalyst for α-Aminoxylation of Aldehydes and Ketones in Ionic Liquids
  作者：Xiong Ding、Wenming Tang、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/adsc.200900652

  日期：2010.1.4

  A novel imidazolium ion‐tagged L‐proline catalyst has been developed. The asymmetric α‐aminoxylation of aldehydes and ketones with excellent enantioselectivities, up to 99% ee, and high yields in ionic liquids has been achieved. The system can be easily recycled and reused for at least six times without significant loss of yields and enantioselectivity.

  新型咪唑鎓离子标记的L-脯氨酸催化剂已经开发出来。醛和酮的不对称α-氨基羟化反应具有出色的对映选择性，高达99％ee的对映选择性以及在离子液体中的高收率。该系统可以轻松地回收再利用至少六次，而收率和对映选择性没有明显损失。
• PROCESSES OF ENANTIOSELECTIVELY FORMING AN AMINOXY COMPOUND AND AN 1,2-OXAZINE COMPOUND
  申请人：Zhong Guofu

  公开号：US20110224429A1

  公开（公告）日：2011-09-15

  Disclosed is a process of enantioselectively forming an aminoxy compound of Formula (3) In formula (3) R 1 is one of an aliphatic group and an alicyclic group. R 2 is one of hydrogen, an aliphatic group, an alicyclic group, an aromatic group, an arylaliphatic group and an arylalicyclic group. R 3 is one of hydrogen, halogen, hydroxyl, and an aliphatic group with a main chain having 1 to about 10 carbon atoms. The respective aliphatic, alicyclic, aromatic, arylaliphatic or arylalicyclic groups of R 1 , R 2 , and R 3 comprise 0 to about 3 heteroatoms independently selected from the group consisting of N, O, S, Se and Si. The process includes contacting a carbonyl compound of Formula (1) and a nitroso compound of Formula (2) in the presence of a chiral catalyst. The chiral catalyst is a compound of Formula (IX)

  本公开了一种选择性形成化合物的过程，该化合物的化学式为（3）。在化学式（3）中，R1是脂肪族基团和脂环族基团中的一种。R2是氢、脂肪族基团、脂环族基团、芳香族基团、芳基脂肪族基团和芳基脂环族基团中的一种。R3是氢、卤素、羟基和主链含有1至约10个碳原子的脂肪族基团中的一种。R1、R2和R3的各自的脂肪、脂环、芳香、芳基脂肪或芳基脂环基团包括独立选择自N、O、S、Se和Si组成的0至约3个杂原子。该过程包括在手性催化剂的存在下接触化合物的化学式（1）和化合物的化学式（2）。该手性催化剂是化合物的化学式（IX）。
• Highly Enantioselective α-aminoxylation Reactions Catalyzed by Isosteviol-proline Conjugates in Buffered Aqueous Media
  作者：Ya-Jie An、Chuan-Chuan Wang、Yuan-Zhen Xu、Wei-Juan Wang、Jing-Chao Tao

  DOI：10.1007/s10562-011-0574-6

  日期：2011.8

  using nitrosobenzene in phosphate buffer solution, resulting in good to high yields and excellent enantioselectivities without using any additives. At pH 9.1, the amphiphilic catalysts showed a pH responsive ability in phosphate buffer solution, which facilitated the excellent O-selectivity reactions, illustrating a viable approach for the development of asymmetric supra-molecular catalysts.Graphical

  通过将 l-脯氨酸与廉价的天然产物异甜菊醇共价连接，设计并合成了手性两亲共轭催化剂。这些催化剂在磷酸盐缓冲溶液中使用亚硝基苯进行醛和酮的不对称 α-氨氧基化反应中表现出显着的效率，在不使用任何添加剂的情况下产生了良好的收率和优异的对映选择性。在 pH 9.1 时，两亲性催化剂在磷酸盐缓冲溶液中表现出 pH 响应能力，促进了优异的 O 选择性反应，说明了开发不对称超分子催化剂的可行方法。
• Direct Proline-Catalyzed Asymmetric α-Aminoxylation of Aldehydes and Ketones
  作者：Yujiro Hayashi、Junichiro Yamaguchi、Tatsunobu Sumiya、Kazuhiro Hibino、Mitsuru Shoji

  DOI：10.1021/jo049338s

  日期：2004.9.1

  The direct proline-catalyzed asymmetric α-aminoxylation of aldehydes and ketones has been developed using nitrosobenzene as an oxygen source, affording α-anilinoxy-aldehydes and -ketones with excellent enantioselectivity. Reaction conditions have been optimized, and low temperature (−20 °C) was found to be a key for the successful α-aminoxylation of aldehydes, while slow addition of nitrosobenzene

  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。