(R)-(+)-N-甲基-1-(1-萘基)乙基胺 | 15297-33-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-(+)-N-甲基-1-(1-萘基)乙基胺
• 中文别名: (R)-(+)-N-甲基-1-(1-萘基)乙胺
• 英文名称: (R)-N-methyl-1-(naphthalen-1-yl)ethanamine
• 英文别名: (1R)-N-methyl-1-naphthalen-1-ylethanamine
• CAS: 15297-33-3
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: YYETYHLXPGYQPZ-SNVBAGLBSA-N

物化性质

• 沸点：
  261 °C(lit.)
• 密度：
  1.041 g/mL at 25 °C(lit.)
• 闪点：
  113 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2921499090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途 

经测试用于对映选择性共轭加成的配体，加成到非外消旋锂有机（氨基）铜酸盐的环烯酮。

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-甲基-1-(1-萘基)乙基胺 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 2.0h， 生成 (R)-N-methyl-1-(naphthalen-1-yl)-N-(pyridin-4-ylmethyl)ethanamine hydrochloride
  参考文献：
  名称：

  Chiral N-benzyl-N-methyl-1-(naphthalen-1-yl)ethanamines and their in vitro antifungal activity against Cryptococcus neoformans, Trichophyton mentagrophytes and Trichophyton rubrum

  摘要：

  In the search for new antifungal compounds and to explore structure activity relationships, a series of 24 chiral benzyl amine type antifungals was synthesised and characterised. In vitro testing against the human pathogen Cryptococcus neoformans revealed that several derivatives had MIC50 values similar to that of the commercial drug Butenafine. All of these contained a bulky group in the para position of the benzyl fragment. Eighteen compounds were also tested for activity against the dermatophytes Trichophyton mentagrophytes and Trichophyton rubrum. Of these (R)-N-(4-tert-butylbenzyI)-N-methyl-1-(naphthalen-1-yl)ethanamine (MIC50,: 0.06 mu g/mL) and a para-benzyloxy substituted derivative (MIC50: 0.125 mu g/mL) possessed high activity. Testing of derivatives with a stereocentre at the benzylic carbon, revealed that (S)-stereochemistry was required for potency: a MIC50 value of 1 mu g/mL was obtained for (S)-1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine. Preparation of the corresponding fluoromethyl compound was achieved employing lipase B from Candida antarctica as catalyst in the key step. A low antifungal activity was observed for the fluorinated derivative indicating the importance of the amine basicity for the antifungal potency of these compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.043
• 作为产物：
  描述：

  (R)-ethyl (1-(naphthalen-1-yl)ethyl)carbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(R)-(+)-N-甲基-1-(1-萘基)乙基胺
  参考文献：
  名称：

  PTC条件下Meldrum酸衍生物的有机催化对映选择性脱羧质子化反应

  摘要：

  一个organocatalyzed对映选择性质子化序列，从容易获得的二取代的麦德鲁姆酸衍生物与酚类，相转移催化（PTC）条件下进行，并开始提供手性非外消旋-芳基2与高达70％的良好的分离收率丙酸酯 EE呈现。富含对映体的（S）-布洛芬的合成证明了该方法的有效性。

  DOI：

  10.1002/ejoc.201800331

文献信息

• COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES
  申请人：Ghosh Arun K.

  公开号：US20110269834A1

  公开（公告）日：2011-11-03

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).

  本文描述了化合物和组合物，以及使用这些化合物和组合物治疗呼吸道疾病和疾病，如严重急性呼吸综合征（SARS）的方法。
• [EN] PROCESS FOR PREPARING CHROMAN COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS CHROMANE
  申请人：LUPIN LTD

  公开号：WO2021100059A1

  公开（公告）日：2021-05-27

  The application relates to a process for manufacturing substituted chroman compounds in an economically scalable manner, without the use of pyrophoric reagents. Also described are synthesis routes that do not include column chromatography purification steps. In particular, the invention relates to the synthesis of the Calcium sensing receptor (CaSR) modulating agent 2-methyl-5-((2R,4S)-2- ((((R)-l-(naphthalen-l-yl)ethyl)amino)methyl)chroman-4-yl)benzoic acid, and pharmaceutically acceptable salts thereof.

  该申请涉及一种以经济可扩展的方式制造取代的色满化合物的过程，无需使用易燃试剂。还描述了不包括柱色谱纯化步骤的合成路线。特别是，该发明涉及合成钙感测受体（CaSR）调节剂2-甲基-5-((2R,4S)-2-((((R)-1-(萘-1-基)乙基)氨基)甲基)色满-4-基)苯甲酸及其药用可接受盐。
• Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host
  作者：Xuefei Huang、Naoko Fujioka、Gennaro Pescitelli、Frank E. Koehn、R. Thomas Williamson、Koji Nakanishi、Nina Berova

  DOI：10.1021/ja020520p

  日期：2002.9.1

  determination of absolute configuration of secondary amines including acyclic and cyclic aliphatic amines, aromatic amines, amino acids, and amino alcohols is described. The chiral substrate is linked to the achiral carrier moiety (3-N-Boc-amino-propyl-N-Boc-amino)acetic acid 1 (BocHNCH(2)CH(2)CH(2)BocNCH(2)COOH), which after deprotection, yields a bidentate conjugate, capable of forming a 1:1 host/guest complex

  描述了用于确定仲胺绝对构型的一般手性实验方案，包括无环和环状脂肪胺、芳香胺、氨基酸和氨基醇。手性底物连接到非手性载体部分（3-N-Boc-氨基-丙基-N-Boc-氨基）乙酸1（BocHNCH（2）CH（2）CH（2）BocNCH（2）COOH），脱保护后，产生双齿缀合物，能够与二聚锌卟啉宿主 2 形成 1:1 的宿主/客体复合物。与早先报道的伯胺和仲醇的情况一样，仲胺缀合物与卟啉镊子宿主的络合图2表示立体分化过程，其中立体中心的大(L)基团(基于构象能A值指定)从卟啉结合口袋突出。这导致形成具有优选的卟啉螺旋的宿主/客体复合物，表现出强烈的激子分裂 CD 光谱。尽管仲胺偶联物的叔酰胺键周围的 Z/E 构象复杂性极大地阻碍了先前的构型分配，但发现卟啉扭曲的手性意义明显受立体中心控制。因此，在取代基的相对空间大小没有歧义的情况下，观察到的 CD 对可以用于直接分配绝对构型。此外，为了将应用扩展
• Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction
  作者：Marek Stankevič

  DOI：10.1039/c4ob02440k

  日期：——

  Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

  用碱金属溶液在液氨中处理具有手性酰胺基官能团的二芳基次膦酸-硼烷酰胺会诱导一个芳基取代基在磷上优先脱芳香化，导致形成非等摩尔量的非对映异构体。脱芳香化的非对映选择性很大程度上取决于手性助剂的结构。
• Synthesis and Evaluation of Chiral Dibenzazepinium Halide Phase-Transfer Catalysts
  作者：Barry Lygo、Bryan Allbutt、Douglas Beaumont、Umar Butt、James Gilks

  DOI：10.1055/s-0028-1087810

  日期：2009.3

  Two complimentary routes to chiral dibenzazepinium halides have been developed. This has enabled the synthesis and evaluation of a range of potential phase-transfer catalysts (PTC) for asymmetric alkylation and Michael addition reactions involving glycine imine esters.

  已开发出两条制备手性二苯并氮杂卓季盐卤化物的互补路线。这使得合成并评估了一系列潜在的相转移催化剂（PTC），可用于涉及甘氨酸亚胺酯的不对称烷基化和迈克尔加成反应。