(1R,2S)-N-亚硝基麻黄碱 | 7181-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,2S)-N-亚硝基麻黄碱
• 英文名称: (1R,2S)-N-nitrosoephedrine
• 英文别名: (+)-N-Nitrosoephedrine；N-Nitroso-L-ephedrin；N-Nitroso-(1S,2R)-ephedrine；N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylnitrous amide
• CAS: 7181-48-8
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: ZVTOLKAVCZXHFM-PSASIEDQSA-N

物化性质

• 熔点：
  82-89 °C
• 沸点：
  380.6±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.9
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-N-亚硝基麻黄碱 在 lithium aluminium tetrahydride 、 lithium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (4S,5R,6S)-3-(2-bromoacetyl)-4,5-dimethyl-6-phenyl-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

  摘要：

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.036
• 作为产物：
  描述：

  α-(甲氨甲基)苯甲醇 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 sodium cyanoborohydride 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.25h， 生成 (1R,2S)-N-亚硝基麻黄碱
  参考文献：
  名称：

  Saavedra, Joseph E.; Farnsworth, David W., Organic Preparations and Procedures International, 1991, vol. 23, # 2, p. 139 - 146

  摘要：

  DOI：

文献信息

• Biosynthesis of porphyrins and related macrocycles. Part 52. Synthesis of (11-S )-[11-2H1]porphobilinogen and the (11R)-enantiomer for stereochemical studies on hydroxymethylbilane synthase (porphobilinogen deaminase)
  作者：Werner L. Neidhart、Paul C. Anderson、Graham J. Hart、Alan R. Battersby

  DOI：10.1039/a904262h

  日期：——

  A synthetic route is devised for the synthesis of (11S)-[11-2H1]porphobilinogen 1a and of the (11R)-enantiomer 1b. Their absolute configurations and enantiomeric purity are established by degradation to a derivative of [2-2H1]glycine of known stereochemistry. Methods are then developed, based on the synthesis of chiral imidate esters, for determination of the configuration of [2H1]-labelled aminomethylpyrroles

  合成路线被设计用于合成（11小号） - [11- 2 ħ 1 ]胆色素原1a和（11 - [R ）-对映体1B。通过降解为已知立体化学的[2- 2 H 1 ]甘氨酸的衍生物，可以确定它们的绝对构型和对映体纯度。然后，基于手性亚氨酸酯的合成，开发了通过将[ 2 H 1 ]标记的氨基甲基吡咯转化为[ 2 H 1 ]标记的am，然后使用1进行分析的方法，来确定[ 2 H 1 ]标记的氨基甲基吡咯的构型。1 H-NMR。PBG 1a和1b的标记样品用作羟甲基胆烷合酶的底物，产物被捕获为[ 2 H 1 ]标记的氨基甲基胆碱7c和7d。它们的构型通过NMR测定法确定，以证明当PBG 1被酶促转化为氨基甲基胆烷7时，在氨基甲基碳上总体上保留了构型。
• THE OXIDATION OF HYDROXYLAMINE BY FREMY’S SALT. PREPARATION OF<i>N</i>-NITROSAMINES AND TETRAZENES
  作者：M. P. Vazaquez Tato、Luis Castedo、Ricardo Riguera

  DOI：10.1246/cl.1985.623

  日期：1985.5.5

  Treatment of secondary amines with Fremy’s salt in aqueous sodium carbonate solution and in the presence of hydroxylamine gives a high yield of either N-nitrosamines or sym-tetrazenes. A mechanism for these conversions is proposed.

  在碳酸钠水溶液中和在羟胺存在下用 Fremy's 盐处理仲胺可得到高产率的 N-亚硝胺或共四氮烯。提出了这些转换的机制。
• Synthesis, in Vitro Activity, and Three-Dimensional Quantitative Structure−Activity Relationship of Novel Hydrazine Inhibitors of Human Vascular Adhesion Protein-1
  作者：Elisa M. Nurminen、Marjo Pihlavisto、László Lázár、Zsolt Szakonyi、Ulla Pentikäinen、Ferenc Fülöp、Olli T. Pentikäinen

  DOI：10.1021/jm100337z

  日期：2010.9.9

  Vascular adhesion protein-1 (VAP-1) belongs to the semicarbazide-sensitive amine oxidases (SSAOs) that convert amines into aldehydes. SSAOs are distinct from the mammalian monoamine oxidases (MAOs), but their substrate specificities are partly overlapping. VAP-1 has been proposed as a target for anti-inflammatory drug therapy because of its role in leukocyte adhesion to endothelium. Here, we describe the synthesis and in vitro activities of novel series of VAP-1 selective inhibitors. In addition, the molecular dynamics simulations performed for VAP-1 reveal that the movements of Met211, Ser496, and especially Leu469 can enlarge the ligand-binding pocket, allowing larger ligands than those seen in the crystal structures to bind. Combining the data from molecular dynamics simulations, docking, and in vitro measurements, the three-dimensional quantitative structure-activity relationship (3D QSAR) models for VAP-1 (q(LOO)(2): 0.636; r(2:) 0.828) and MAOs (q(LOO)(2): 0.749, r(2): 0.840) were built and employed in the development of selective VAP-1 inhibitors.
• Base-induced fragmentation of .beta.-hydroxy nitrosamines
  作者：R. N. Loeppky、W. A. McKinley、L. G. Hazlitt、J. R. Outram

  DOI：10.1021/jo00146a003

  日期：1982.12