(1S,2S)-N-benzoylpseudoephedrine | 442669-65-0

• 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: (1S,2S)-N-benzoylpseudoephedrine
• 英文别名: (+)-N-benzoyl-pseudoephedrine；(+)-N-Benzoyl-pseudoephedrin；N-((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-aethyl)-N-methyl-benzamid; N-Benzoyl-(+)-pseudoephedrin；(1S,2S)-1-phenyl-2-(N-methyl-N-benzoylamino)-1-propanol；(+)-N-Benzoyl-φ-ephedrin；N-[(1S,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylbenzamide
• CAS: 442669-65-0
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: RLEBYZJBMZZXSZ-XJKSGUPXSA-N

物化性质

• 沸点：
  456.3±38.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  盐酸 、 (1S,2S)-N-benzoylpseudoephedrine 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Mechanism and Stereochemical Course of Acyl Migrations in Derivatives of Ephedrine and ψ-Ephedrine

  摘要：

  DOI：

  10.1021/ja01178a071
• 作为产物：
  描述：

  2-(N-benzoyl-N-methylamino)-1-phenyl-1-propanone 在 ruthenium(II) chloride 、 (1R,2R)-N'-[[4-[(4-ethenylphenyl)methoxy]phenyl]methyl]-1,2-diphenylethane-1,2-diamine 、 potassium tert-butylate 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 、 叔丁醇 为溶剂， 20.0 ℃ 、1.0 MPa 条件下， 反应 2.0h， 生成 (1S,2S)-N-benzoylpseudoephedrine
  参考文献：
  名称：

  Polymer-Immobilized Catalyst for Asymmetric Hydrogenation of Racemic α-(N-Benzoyl-N-methylamino)propiophenone

  摘要：

  Asymmetric hydrogenation of alpha-(N-benzoyl-N-methylamino)propiophenone through dynamic kinetic resolution was performed by using a polymer-immobilized chiral diamine-ruthenium-BINAP-t-BuOK system in order to yield syn-beta-amide alcohol exclusively with nearly perfect enantioselectivity.

  DOI：

  10.1021/jo802339t

文献信息

• Synthesis and X-ray crystallography of new <i>N-, O-</i>acyl pseudoephedrines
  作者：Eman A. Ahmed、Khaled M. Mohamed、Shymaa A. Thabet、Amr H. Moustafa、Ahmed F. Mabied、Ahmed Khodairy

  DOI：10.1080/00397911.2023.2207127

  日期：2023.7.3

  pseudoephedrine or its salt with benzoyl or p-nitrobenzoyl chlorides affords the corresponding N- or O-acylated products 2a, b, 3a, b and 4. Also, pseudoephedrine 1 was allowed to react with ethoxymethylenemalononitrile to yield 2-hydroxy-1-methyl-2-phenylethyl](methyl)amino}methylene)malononitrile (5). New oxazolidine derivatives 6a–c were conveniently synthesized in high yields from the reaction of 1 with different

  摘要 以芳酰氯和/或氯甲酸乙酯为酰化剂，研究了伪麻黄碱的N-酰化和O-酰化。因此，用苯甲酰氯或对硝基苯甲酰氯处理伪麻黄碱或其盐，得到相应的N-或O-酰化产物2a、b、3a、b和4。此外，允许伪麻黄碱1与乙氧基亚甲基丙二腈反应，生成 2-羟基-1-甲基-2-苯乙基](甲基)氨基}亚甲基)丙二腈(5)。新的恶唑烷衍生物6a–c由1的反应以高产率方便地合成与不同的双（甲硫基）亚丁腈。4的 X 射线晶体学研究表明该化合物在正交晶系中结晶。该结构通过分子间相互作用以及氢键接触网络、一致的平行层来稳定。
• RUTHENIUM COMPOUND AND METHOD FOR PRODUCING OPTICALLY ACTIVE AMINOALCOHOL COMPOUND
  申请人：Nippon Soda Co., Ltd.

  公开号：EP2264000A1

  公开（公告）日：2010-12-22

  A novel ruthenium compound that is useful as an asymmetric reduction catalyst for carbonyl compounds. The ruthenium compound of the present invention is represented by a formula (I): (Ru(X)2(Pxx)[R1R2C(NH2)-R3R4C(NH2)] (I)), and when this compound is used as an asymmetric reduction catalyst, an optically active aminoalcohol compound can be produced from an a-aminoketone, and particularly a compound represented by formula (IV), with high stereoselectivity and high yield.

  一种可用作羰基化合物不对称还原催化剂的新型钌化合物。本发明的钌化合物由式（I）表示：(Ru(X)2(Pxx)[R1R2C(NH2)-R3R4C(NH2)](I))，当该化合物用作不对称还原催化剂时，可以高立体选择性和高产率从a-氨基酮制得光学活性氨基醇化合物，特别是由式(IV)表示的化合物。
• Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process
  作者：Sergei F. Vasilevsky、Maria P. Davydova、Victor I. Mamatuyk、Nadezhda V. Pleshkova、Dmitry S. Fadeev、Igor V. Alabugin

  DOI：10.1016/j.mencom.2015.09.021

  日期：2015.9

  Reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with (+)-pseudoephedrine leads to products of alkyne moiety cleavage, namely, 1-(3,4,5-trimethoxyphenyl)ethanone and N-(1-hydroxy-1-phenylprop-2-yl)-N-methylbenzamides. In the course of the process one of alkyne carbons undergoes a formal reduction to a Me group, whereas the other one is oxidized to a C(O)NRR' moiety.
• METHOD FOR PRODUCING OPTICALLY ACTIVE AMINOALCOHOL COMPOUND USING RUTHENIUM COMPOUND
  申请人：Nippon Soda Co., Ltd.

  公开号：EP2264000B1

  公开（公告）日：2016-05-11
• US8207379B2
  申请人：——

  公开号：US8207379B2

  公开（公告）日：2012-06-26