特比萘芬杂质 | 151222-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 特比萘芬杂质
• 中文别名: 特比萘芬相关化合物D(USP)；4-甲基特比萘芬；特比萘芬杂质D(EP/BP)；特比萘芬EP杂质D
• 英文名称: 4-Methylterbinafine
• 英文别名: (E)-N,6,6-trimethyl-N-[(4-methylnaphthalen-1-yl)methyl]hept-2-en-4-yn-1-amine
• CAS: 151222-50-3
• 化学式: C₂₂H₂₇N
• 分子量: 305.463
• InChiKey: DRWRMSGOBQMKBI-UXBLZVDNSA-N

物化性质

• 沸点：
  432.8±33.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-氯-6,6-二甲基-2-庚烯-4-炔; 6,6-二甲基-2-烯-4-炔氯代庚烷 、 1-(溴甲基)-4-甲基萘 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到特比萘芬杂质
  参考文献：
  名称：

  Synthesis and structure-activity relationships of naphthalene-substituted derivatives of the allylamine antimycotic terbinafine

  摘要：

  Derivatives of the allylamine antimycotic terbinafine (1) with varied substitution at the naphthalene ring system have been prepared, and their antifungal activity has been evaluated. In general, the potency is strongly dependent on the bulkiness of the substituent. Only hydrogen or in some cases fluorine are tolerated as substituents at positions 2-4 and 6-8 of the naphthalene moiety, whereas 5-substituents may be larger in size (F, Cl, Br, Me). Derivatives with fluorine at positions 3, 5, and 7 or chlorine at position 5 showed enhanced activity against yeasts relative to 1. This increase in sensitivity could be intensified by simultaneous introduction of two fluoro substituents at positions 5 and 7. Compound 7q demonstrated 8-to 16-fold improved potency against Aspergillus fumigatus, Candida albicans, and Candida parapsilosis.

  DOI：

  10.1021/jm00071a011

文献信息

• [EN] PROCESS FOR PREPARING TERBINAFINE<br/>[FR] PROCEDE DE PREPARATION DE TERBINAFINE
  申请人：REDDYS LAB LTD DR

  公开号：WO2007044273A1

  公开（公告）日：2007-04-19

  [EN] A process for preparing terbinafine or a salt thereof having high purity.
  [FR] L'invention concerne un procédé de préparation de terbinafine ou un sel de celle-ci présentant une haute pureté.
• Synthesis and structure-activity relationships of naphthalene-substituted derivatives of the allylamine antimycotic terbinafine
  作者：Peter Nussbaumer、Gerhard Dorfstaetter、Ingrid Leitner、Karin Mraz、Hermann Vyplel、Anton Stuetz

  DOI：10.1021/jm00071a011

  日期：1993.9

  Derivatives of the allylamine antimycotic terbinafine (1) with varied substitution at the naphthalene ring system have been prepared, and their antifungal activity has been evaluated. In general, the potency is strongly dependent on the bulkiness of the substituent. Only hydrogen or in some cases fluorine are tolerated as substituents at positions 2-4 and 6-8 of the naphthalene moiety, whereas 5-substituents may be larger in size (F, Cl, Br, Me). Derivatives with fluorine at positions 3, 5, and 7 or chlorine at position 5 showed enhanced activity against yeasts relative to 1. This increase in sensitivity could be intensified by simultaneous introduction of two fluoro substituents at positions 5 and 7. Compound 7q demonstrated 8-to 16-fold improved potency against Aspergillus fumigatus, Candida albicans, and Candida parapsilosis.