(1S,2R)-(+)-N-乙酰基麻黄碱 | 2272-83-5

• 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: (1S,2R)-(+)-N-乙酰基麻黄碱
• 英文名称: (1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid
• 英文别名: N-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide；N-((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-aethyl)-N-methyl-acetamid；(1R:2S)-2-(Methyl-acetyl-amino)-1-phenyl-propanol-(1)；N-acetyl ephedrine；N-[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide
• CAS: 2272-83-5
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: ZZGMTCKULVMTDB-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  麻黄碱	ephedrine	299-42-3	C10H15NO	165.235
  麻黄素	(1S,2R)-(+)-ephedrine	321-98-2	C10H15NO	165.235

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  [R-(R*,S*)]-alpha-[1-(乙基甲基氨基)乙基]苄醇	(1R,2S)-1-phenyl-2-(ethylmethylamino)propanol	48141-64-6	C12H19NO	193.289
  ——	(S)-(+)-N-Acetyl-N-methylamphetamine	89617-55-0	C12H17NO	191.273
  麻黄碱	ephedrine	299-42-3	C10H15NO	165.235
  (1S,2S)-2-甲氨基-1-苯基丙-1-醇	pseudoephedrine	90-82-4	C10H15NO	165.235

反应信息

• 作为反应物：
  描述：

  (1S,2R)-(+)-N-乙酰基麻黄碱 在 镍 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以71.7%的产率得到(S)-(+)-N-Acetyl-N-methylamphetamine
  参考文献：
  名称：

  WO2006/67794

  摘要：

  公开号：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 生成 (1S,2R)-(+)-N-乙酰基麻黄碱
  参考文献：
  名称：

  �ber die Acetylierung von Adrenalin

  摘要：

  DOI：

  10.1007/bf00898985

文献信息

• Comparison of diffusion coefficients for matched pairs of macrocyclic and linear molecules over a drug-like molecular weight range
  作者：Andrew R. Bogdan、Nichola L. Davies、Keith James

  DOI：10.1039/c1ob05996c

  日期：——

  The diffusion coefficients of a series of closely matched pairs of macrocyclic and linear molecules have been compared using NMR spectroscopy. The macrocyclic series was designed both to overlap with and extend beyond the molecular weight range typically employed for drug-like molecules. The linear molecules each represent a carbogenic fission of their macrocyclic counterparts, designed to minimize differences in functionality and physicochemical properties. Each series of molecules was prepared using copper catalyzed azide-alkyne cycloaddition (CuAAC) reactions conducted in a flow using a copper tube. The macrocyclic series exhibited consistently higher diffusion across the entire molecular weight range studied. The fold difference in diffusion coefficients between the macrocyclic and linear analogues appeared to be independent of either solvent viscosity or dielectric environment.

  通过核磁共振波谱法比较了一系列紧密匹配的大环和线性分子对的扩散系数。大环系列的设计既与通常用于类药物分子的分子量范围重叠，又有所扩展。每个线性分子代表了其相应大环分子的碳解裂变，旨在最小化功能和物理化学性质的差异。每个分子系列均采用铜催化的叠氮-炔环加成（CuAAC）反应，在流动体系中使用铜管进行制备。在整个研究分子量范围内，大环系列始终展现出更高的扩散性。大环和线性类似物之间扩散系数的倍数差异似乎与溶剂粘度或介电环境无关。
• Heterocyclic inhibitors of ERK2 and uses thereof
  申请人：Cao Jingrong

  公开号：US20070265263A1

  公开（公告）日：2007-11-15

  Described herein are compounds that are useful as protein kinase inhibitors having the formula: wherein Z 1 and Z 2 are each independently nitrogen or CH and Ring A, T m R 1 , QR 2 , U n R 3 , and Sp are as described in the specification. The compounds are especially useful as inhibitors of ERK2 and for treating diseases in mammals that are alleviated by a protein kinase inhibitor, particularly diseases such as cancer, inflammatory disorders, restenosis, diabetes, and cardiovascular disease.

  本文介绍了一些具有下列式的蛋白激酶抑制剂的化合物： 其中Z1和Z2各自独立地为氮或CH，环A、TmR1、QR2、UnR3和Sp如说明书所述。这些化合物特别适用于抑制ERK2并治疗哺乳动物中由蛋白激酶抑制剂缓解的疾病，特别是癌症、炎症性疾病、再狭窄、糖尿病和心血管疾病等疾病。
• A Process for the Preparation of R-(-)-N, Alpha-Dimethylphenethylamine (Levmethamfetamine) or S-(+)-N, Alpha-Dimethylphenethylamine (Methamphetamine) from D-Ephendrine, or L-Ephedrine Respectively
  申请人：Gollapudy Subrahmanyam

  公开号：US20080293971A1

  公开（公告）日：2008-11-27

  A process for synthesis of R-(−)-N,α-Dimethylphenethylamine (Levmetamfetamine, formula I), or S-(+)-N,α-Dimethyl phenethylamine (Methamphetamine, formula II), from d-ephedrine of formula III or l-ephedrine formula IV, the process comprising the steps of (a) acylating the d- or l-ephedrine base of formula III or formula IV with an acylating agent to make a reaction mixture containing a N-acylated ephedrines of formula V or formula VI; (b) deoxygenation of N-acylated ephedrines to make the compound of the formula VII or Formula VIII by using Raney Nickel catalyst; and (c) acid hydrolysis of the above deoxygenated products to get the levmetamfetamine or methamphetamine.

  一种从d-麻黄碱（式III）或l-麻黄碱（式IV）合成R-（-）-N，α-二甲基苯乙胺（左旋甲基苯丙胺，式I）或S-（+）-N，α-二甲基苯乙胺（甲基苯丙胺，式II）的方法，该方法包括以下步骤：（a）用酰化剂酰化式III或式IV的d-或l-麻黄碱基，制备含有式V或式VI的N-酰化麻黄碱的反应混合物；（b）使用Raney镍催化剂脱氧N-酰化麻黄碱，制备式VII或式VIII的化合物；（c）对上述脱氧产物进行酸水解，得到左旋甲基苯丙胺或甲基苯丙胺。
• Reaktionen von (−)-Ephedrin bzw. (+)-Norpseudoephedrin und Derivaten mit N,N-Dimethylacetamid-dimethylacetal und N,N,-Dimethylformamid-dimethylacetal
  作者：M. Köhl、H. Spreitzer、W. Fleischhacker

  DOI：10.1007/bf00811546

  日期：1992.10
• Tytgat, D.; Gelbcke, M., Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 6, p. 479 - 490
  作者：Tytgat, D.、Gelbcke, M.

  DOI：——

  日期：——