(-)-N-propylephedrine | 75082-00-7

• 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: (-)-N-propylephedrine
• 英文别名: (1R,2S)-2-(methyl-propyl-amino)-1-phenyl-propan-1-ol；N-Propyl-(-)-ephedrin；(1R,2S)-2-(Methyl-propyl-amino)-1-phenyl-propan-1-ol; N-Propyl-(-)-ephedrin；(1R,2S)-2-[methyl(propyl)amino]-1-phenylpropan-1-ol
• CAS: 75082-00-7
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: MMMVOMOZOGUPRJ-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  麻黄碱 在 sodium hydroxide 、 硼烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.5h， 生成 (-)-N-propylephedrine
  参考文献：
  名称：

  Design of mesoporous aluminosilicates supported (1R,2S)-(−)-ephedrine: evidence for the main factors influencing catalytic activity in the enantioselective alkylation of benzaldehyde with diethylzinc

  摘要：

  (-)-麻黄碱被用作模型β-氨基醇，通过卤代烷基(芳基)硅烷链之前接枝在介孔胶束模板铝硅酸盐(Al-MTS)表面的亲核取代反应，将其共价键合到介孔胶束模板铝硅酸盐上。共价接枝可以通过两种方法进行：方法a为硅烷化，方法b为表面溶胶-凝胶法。后者提供了更高的负载量，但较高的负载量会降低介孔体积。随后，将连接基的卤代烷基部分替换成(1R,2S)-(-)-麻黄碱。在异相手性选择性催化苯甲醛与二乙基锌的烷基化反应中，这些材料用作手性辅剂，显示的性能主要取决于接枝方法。具有高初始孔径的载体制备的催化剂表现出最佳的活性和对映选择性。研究表明介孔的规则孔结构对反应效率和对映选择性有显著影响。此外，还研究了烷基化对活性部位的稀释效应以及连接基的刚性化效应。©2002 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0957-4166(02)00103-9

文献信息

• Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation
  作者：Françoise Hénin、Stéphane Létinois、Jacques Muzart

  DOI：10.1016/s0040-4039(97)01728-0

  日期：1997.10

  hydrogen and catalytic amounts of Pd/C induced the formation of 1,3-oxazolidines from nitriles and 1,2-amino alcohols. The subsequent reductive cleavage of the NCO bond of these heterocycles occurred under the same conditions. Thus, this methodology provides a new one-pot N-alkylation of 1,2-amino alcohols using nitriles as reagents with yields up to 98%.

  在室温下，氢的存在和催化量的Pd / C导致腈和1,2-氨基醇形成1,3-恶唑烷。这些杂环的NC ＝ O键的随后还原裂解在相同条件下发生。因此，该方法使用腈作为试剂，提供了新的一锅法1,2-氨基醇的N-烷基化反应，收率高达98％。
• Studies on Syntheses and Pharmacological Effects of N-Alkylephedrines and their Ammonium Salt Derivatives
  作者：Takeo Ueda、Shigeshi Toyoshima、Kiyoshi Takahashi、Masako Muraoka

  DOI：10.1248/cpb1953.3.465

  日期：——

  N-Alkylephedrines were synthesized by heating a mixture of ephedrine and alkyl bromide under pressure. The alkylation proceeded with decreasing yield of the desired substance as the number of carbons of alkyl bromide increased, and there was, in the end, no yield at C5, viz., amyl bromide. With alkyl bromides of higher moleculer weight than amyl, the alkylation was successfully carried out by the addition of equimolar amount of pulverized KOH. The N-alkylephedrines thus obtained were converted to the ammonium salts with methyl or ethyl iodide. The pharmacological effects of the compounds synthesized were examined by the Magnus method and these effects were compared with that of l-ephedrine. Among these compounds, N-butyl-, N-hexyl-, N-heptylephedrines, and dimethylbutyl-(β-phenyl-β-hydroxyisopropyl) ammonium iodide were found to have pharmacological effects almost equal to that of l-ephedrine, in the balance of inhibitory effect on tonic contractions by acetylcholine, histamine, and barium chloride.

  N-烷基麻黄碱是通过在压力下加热麻黄碱和烷基溴的混合物来合成的。随着烷基溴的碳数增加，烷基化进行，所需物质的收率降低，并且最终没有产生C5即戊基溴。对于分子量高于戊基的烷基溴，通过添加等摩尔量的粉状KOH成功地进行烷基化。将由此获得的N-烷基麻黄碱用甲基或乙基碘转化成铵盐。通过马格努斯法检测了合成的化合物的药理作用，并与l-麻黄碱的药理作用进行了比较。在这些化合物中，发现N-丁基-、N-己基-、N-庚基麻黄碱和二甲基丁基-(β-苯基-β-羟基异丙基)碘化铵的药理作用几乎与L-麻黄碱相同，平衡乙酰胆碱、组胺和氯化钡对强直收缩的抑制作用。
• Pharmaceutically Active Diazepanes
  申请人：Oberhauser Berndt

  公开号：US20080300237A1

  公开（公告）日：2008-12-04

  Leukocyte Function-Associated Antigen One (LFA-1) is a cell adhesion molecule selectively expressed on leukocytes, and plays a major role in the activation and trafficking of T lymphocytes in the tissue at sites of inflammation. In the last decade a large body of preclinical data has accumulated to establish the importance of LFA-1 as a biological target, 10 particularly in chronic, T-cell driven inflammatory conditions. The present invention provides pharmaceutically active 1,4-diazepan-2-ones of formula I useful for the treatment of conditions related to LFA-1 activity.

  白细胞功能相关抗原一（LFA-1）是一种细胞黏附分子，选择性地表达在白细胞上，对于在炎症部位的组织中T淋巴细胞的激活和转移起着重要作用。在过去的十年中，大量的临床前数据已经积累，以确定LFA-1作为生物学靶点的重要性，特别是在慢性的、T细胞驱动的炎症情况下。本发明提供了公式I的药物活性1,4-二氮杂环己烷-2-酮，用于治疗与LFA-1活性相关的疾病。
• Chaloner, Penny A.; Langadianou, Eugenia; Perera, S. A. Renuka, Journal of the Chemical Society. Perkin transactions I, 1991, p. 2731 - 2735
  作者：Chaloner, Penny A.、Langadianou, Eugenia、Perera, S. A. Renuka

  DOI：——

  日期：——
• PHARMACEUTICALLY ACTIVE DIAZEPANES
  申请人：Novartis AG

  公开号：EP1874739B1

  公开（公告）日：2010-05-26