1-(bromomethyl)-5,7-difluoronaphthalene | 110931-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(bromomethyl)-5,7-difluoronaphthalene
• 英文别名: 5,7-difluoro-1-bromomethylnaphthalene；5-(bromomethyl)-1,3-difluoronaphthalene
• CAS: 110931-63-0
• 化学式: C₁₁H₇BrF₂
• 分子量: 257.077
• InChiKey: WXCWDIIQICPXDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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-(bromomethyl)-5,7-difluoronaphthalene 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Pyrido[2,1-c][1,4]oxazine, benzamide deriv.
  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
• 作为产物：
  描述：

  1,3-二氟苯 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 氯化亚砜 、 三苯基甲醇 、 amalgamated zinc 、 氢气 、 溶剂黄146 、 三氟乙酸 、 三氟乙酸酐 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醚 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 64.0h， 生成 1-(bromomethyl)-5,7-difluoronaphthalene
  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

• Amine derivatives, processes for their production and their use
  申请人：Sandoz, Ltd.

  公开号：US04939148A1

  公开（公告）日：1990-07-03

  Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## and R.sub.2 represents hydrogen or lower alkyl, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached represent a group of formula IIg ##STR3## R.sub.4 and R.sub.5 represent independently hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl or halogenalkyl and R.sub.6 represents a group of formula ##STR4## R.sub.1 represents a group of formula IIa to IIf as defined above, R.sub.2 and R.sub.3 together form a --(CH.sub.2)--.sub.u group wherein u stands for a whole number from 1 to 8 and R.sub.4, R.sub.5 and R.sub.6 have the meanings given above. which compounds are indicated for use as pharmaceuticals and agrochemicals.

  化合物的化学式I ##STR1## 中，其中R.sub.1代表化学式##STR2## 的基团，R.sub.2代表氢或较低的烷基，或者R.sub.1和R.sub.2与它们连接的碳原子一起代表化学式IIg ##STR3## 的基团，R.sub.4和R.sub.5独立地代表氢或较低的烷基，R.sub.3代表氢、烷基、环烷基或卤代烷基，R.sub.6代表化学式##STR4## 的基团，R.sub.1代表如上定义的化学式IIa到IIf的基团，R.sub.2和R.sub.3一起形成一个--(CH.sub.2)--.sub.u基团，其中u代表从1到8的整数，R.sub.4、R.sub.5和R.sub.6具有上述给定的含义。这些化合物被指示用作药物和农药。
• Nussbaumer, Peter; Leitner, Ingrid; Stuetz, Anton, Medicinal Chemistry Research, 1995, vol. 5, # 7, p. 515 - 521
  作者：Nussbaumer, Peter、Leitner, Ingrid、Stuetz, Anton

  DOI：——

  日期：——
• NUSSBAUMER, PETER;STUTZ, ANTON;VYPLEL, HERMANN
  作者：NUSSBAUMER, PETER、STUTZ, ANTON、VYPLEL, HERMANN

  DOI：——

  日期：——
• US4939148A
  申请人：——

  公开号：US4939148A

  公开（公告）日：1990-07-03
• US5112851A
  申请人：——

  公开号：US5112851A

  公开（公告）日：1992-05-12