特比萘芬 im B | 78628-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 特比萘芬 im B
• 中文别名: 特比萘芬imB
• 英文名称: (Z)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine
• 英文别名: (Z)-N,6,6-trimethyl-N-(naphth-1-ylmethyl)hept-2-en-4-yn-1-amine；N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthylmethyl amine；Terbinafine, (Z)-；(Z)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
• CAS: 78628-81-6
• 化学式: C₂₁H₂₅N
• 分子量: 291.436
• InChiKey: DOMXUEMWDBAQBQ-UITAMQMPSA-N

物化性质

• 沸点：
  417.9±33.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  特比萘芬 生成 特比萘芬 im B
  参考文献：
  名称：

  FUNFSCHILLING, PETER;RUCKTASCHEL, RUDOLF

  摘要：

  DOI：

文献信息

• Synthesis and antifungal activity of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine (SF 86-327) and related allylamine derivatives with enhanced oral activity
  作者：Anton Stuetz、Gabor Petranyi

  DOI：10.1021/jm00378a003

  日期：1984.12

  The allylamine derivatives are a new class of synthetic antifungal agents inhibiting fungal squalene epoxidase. A new subclass, which features an acetylene group conjugated with the allylamine double bond, is characterized by enhanced antifungal activity, especially on oral treatment of guinea pig dermatophytoses. Increased branching of the alkyl group next to the triple bond led to the tert-butylacetylene

  烯丙胺衍生物是抑制真菌角鲨烯环氧酶的一类新的合成抗真菌剂。一个新的亚类，具有与烯丙基胺双键结合的乙炔基团，其特点是增强的抗真菌活性，特别是在豚鼠皮肤癣菌的口服治疗中。靠近三键的烷基支链的增加导致了叔丁基乙炔衍生物SF 86-327，该化合物在体内外的活性均显着提高，目前正在临床评估中。介绍了通用的合成路线，可比较的生物学数据以及构效关系。
• Process for the preparation of terbinafine and salts thereof
  申请人：Kaspi Joseph

  公开号：US20060004230A1

  公开（公告）日：2006-01-05

  A process for the preparation of Terbinafine and salts thereof by reacting 1-chloro-6,6-dimethylhept-2-en-4-yne and N-methyl-N-(1-naphthylmethyl)amine in a basic aqueous medium is disclosed. Also disclosed is a process for the preparation of 1-chloro-6,6-dimethylhept-2-en-4-yne.

  通过在碱性水性介质中使1-氯-6,6-二甲基庚-2-烯-4-炔和N-甲基-N-(1-萘甲基)胺反应，揭示了一种制备特比萘和其盐的方法。还揭示了一种制备1-氯-6,6-二甲基庚-2-烯-4-炔的方法。
• Identification of impurities in the production of terbinafine hydrochloride
  作者：P. V. Kazakov、S. N. Golosov

  DOI：10.1007/s11094-006-0150-3

  日期：2006.8

  The purity of the parent substance of (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-1-ylmethylamine (terbinafine) is evaluated via TLC identification of the main impurities appearing during its synthesis via alkylation of N-methylnaphth-1-ylmethylamine with 1-chloro-6,6-dimethyl-2-hept-2-en-4-yne The possible formation of impurities including N-methyl-N,N-di(methylnaphth-1-yl)amine, N-methylnaphth-1-ylmethylamine, N-methylnaphth-2-ylmethylamine, (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-1-ylmethylamine, (Z)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-1-ylmethylamine, (E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-2-ylmethylamine, and (Z)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methylnaphth-2-ylmethylamine was confirmed by means of countersynthesis.

  (E)-N-(6,6-二甲基庚-2-烯-4-炔基)-N-甲基萘-1-基甲基胺（特比萘芬）母体物质的纯度通过薄层色谱法鉴定其在合成过程中出现的主要杂质来评估，该合成过程是通过N-甲基萘-1-基甲基胺与1-氯-6,6-二甲基-2-庚-2-烯-4-炔的烷化反应进行的。通过反合成法确认了可能形成的杂质，包括N-甲基-N,N-二(甲基萘-1-基)胺、N-甲基萘-1-基甲基胺、N-甲基萘-2-基甲基胺、(E)-N-(6,6-二甲基庚-2-烯-4-炔基)-N-甲基萘-1-基甲基胺、(Z)-N-(6,6-二甲基庚-2-烯-4-炔基)-N-甲基萘-1-基甲基胺、(E)-N-(6,6-二甲基庚-2-烯-4-炔基)-N-甲基萘-2-基甲基胺和(Z)-N-(6,6-二甲基庚-2-烯-4-�
• Purification process
  申请人：Beutler Ulrich

  公开号：US20050197512A1

  公开（公告）日：2005-09-08

  Process for the preparation of pure allylamine pharmaceutical terbinafine of formula I in free base form or acid addition salt form, by distilling crude terbinafine base, preferably by short path distillation, e.g. at a temperature above 100° C. and reduced pressure, e.g. 0.2 mbar, and recovering the purified product in free base or acid addition salt form. The process is indicated for use in removal of metal or non-metal contaminants, optionally together with salt formation under simultaneous precipitation of pure trans isomer. Detection of non-metal contaminants such as substance A of formula preferably is effected by RP HPLC analysis with UV detection.

  制备纯烯丙胺药物特比那芬（化学式I）的过程，可以得到其自由碱基形式或酸盐加成物形式，方法是通过蒸馏粗特比那芬碱基，最好是通过短程蒸馏，例如在温度高于100℃和减压下（例如0.2毫巴）进行，然后以自由碱基或酸盐加成物形式回收纯净产品。该过程适用于去除金属或非金属污染物，可选地与盐形成同时沉淀纯的顺式异构体。检测非金属污染物，例如化合物A的公式，最好是通过RP HPLC分析与紫外线检测进行。
• PURIFICATION PROCESS
  申请人：Beutler Ulrich

  公开号：US20100087545A1

  公开（公告）日：2010-04-08

  Process for the preparation of pure allylamine pharmaceutical terbinafine of formula I in free base form or acid addition salt form, by distilling crude terbinafine base, preferably by short path distillation, e.g. at a temperature above 100° C. and reduced pressure, e.g. 0.2 mbar, and recovering the purified product in free base or acid addition salt form. The process is indicated for use in removal of metal or non-metal contaminants, optionally together with salt formation under simultaneous precipitation of pure trans isomer. Detection of non-metal contaminants such as substance A of formula preferably is effected by RP HPLC analysis with UV detection.

  制备纯烯丙胺药物特比那菲（化学式I）的过程，可得到其自由碱基形式或酸盐加成盐形式，方法是通过蒸馏粗特比那菲碱基，最好采用短程蒸馏，例如在100℃以上和减压条件下（例如0.2毫巴），并以自由碱基或酸盐加成盐形式回收纯化后的产品。该过程适用于去除金属或非金属杂质，可选择与盐形成同时沉淀纯的顺式异构体。检测非金属杂质，例如化合物A的公式，最好采用RP HPLC分析与紫外线检测。