7-(bromomethyl)-3-chlorobenzothiophene | 88415-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 7-(bromomethyl)-3-chlorobenzothiophene
• 英文别名: 7-(Bromomethyl)-3-chloro-1-benzothiophene
• CAS: 88415-30-9
• 化学式: C₉H₆BrClS
• 分子量: 261.57
• InChiKey: XGGSRBQIYRWZNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-(bromomethyl)-3-chlorobenzothiophene 、 N-[4-(1-Methyl-1-phenylethyl)benzyl]-methylamine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到[(3-Chlorobenzo[b]thiophen-7-yl)methyl]methyl{[4-(1-methyl-1-phenylethyl)phenyl]methyl}amine
  参考文献：
  名称：

  苯基取代的苄胺类抗真菌药的合成与构效关系：一种用于全身治疗的新型苄基苄胺类抗真菌剂。

  摘要：

  已经制备了在侧链上掺有额外苯环的苄胺类抗真菌药的衍生物，并评估了它们的抗真菌活性。效力强烈取决于两个苯基之间的距离和间隔基的类型。将芳基环与季碳原子连接导致鉴定出具有新的4-苄基苄胺侧链的高活性化合物7f和12a。化合物7f及其7-苯并[b]噻吩基类似物12a表现出显着增强的功效，尤其是对白色念珠菌的抵抗力，并且是迄今为止鉴定出的最有效的烯丙基/苄胺类抗真菌药。对苄基苄胺衍生物7f的深入研究表明，除了增强的抗真菌特性外，

  DOI：

  10.1021/jm00067a010
• 作为产物：
  描述：

  7-甲基-苯并[b]噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 氯 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醚 、 正己烷 为溶剂， 反应 4.0h， 生成 7-(bromomethyl)-3-chlorobenzothiophene
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011

文献信息

• Intermediates for producing enyne derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05436354A1

  公开（公告）日：1995-07-25

  (E)-N-(3-Chloro-2-propenyl)-N-methyl-1naphthylenemethanamine and (E)-3-chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b]thiophene-7-methanami ne which are useful as intermediates in the production of enyne compounds which exhibit squalene epoxidase inhibiting activity and anti-Eumycetes activity.

  (E)-N-(3-氯-2-丙烯基)-N-甲基-1-萘甲胺和(E)-3-氯-N-(3-氯-2-丙烯基)-N-甲基苯并[b]噻吩-7-甲胺是在生产具有角鲨烷环氧酶抑制活性和抗真菌活性的炔烃化合物中有用的中间体。
• Process for producing enyne Derivatives
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0645369A2

  公开（公告）日：1995-03-29

  The invention relates to compounds of the formula wherein R11 is a hydrogen atom, a lower alkyl group, a halo lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R21 is a hydrogen atom or a group of the formula wherein each of R3, R31 and R32, which may be the same or different, is a hydrogen atom or a lower alkyl group, each of R4, R5, R41 and R51, which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group, and R42 is a hydroxyl group, a halogen atom, a group of the formula B-O (wherein B is a protecting group for a hydroxyl group), a hydroxy methyl group, a formyl group, a carboxyl group, a lower alkoxy carbonyl group, a lower alkanoyl group, an amino group, a mercapto group or a group of the formula R6-X-Y-(wherein R6 is a phenyl or thienyl group which may have one or two substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower one or two substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower alkyl group, a cyano group, a lower alkoxy group and a heterocyclic group, each of X and Y, which may be the same or different, is an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHRa- (wherein Ra is a hydrogen atom or a lower alkyl group) or a group of the formula -NRb- (wherein Rb is a hydrogen atom or a lower alkyl group), or X and Y together form a vinylene group or an ethynylene group), provided that when either one of X and Y is an oxygen atom, a sulfur atom or a group of the formula -NRb- (wherein Rb is as defined above), the other is a carbonyl group or a group of the formula -CHRa- (wherein Ra is as defined above), and W is a halogen atom, and a process for preparing such compounds.

  本发明涉及式如下的化合物 其中 R11 是氢原子、低级烷基、卤代低级烷基、低级烯基、低级炔基或环烷基； R21 是氢原子或式中的基团 其中 R3、R31 和 R32（可以相同或不同）各自是氢原子或低级烷基，R4、R5、R41 和 R51（可以相同或不同）各自是氢原子、卤素原子、羟基、低级烷基或低级烷氧基，R42 是羟基、卤素原子、式 B-O 的基团（其中 B 是羟基的保护基）、羟甲基、甲酰基、羧基、低级烷氧基羰基、低级烷酰基、氨基、巯基或式 R6-X-Y- （其中 R6 为苯基或噻吩基，可具有一个或两个选自卤素原子、羟基、一个或两个选自卤素原子的低级取代基、羟基、低级烷基、氰基、低级烷氧基和杂环基，X 和 Y（可以相同或不同）分别是氧原子、硫原子、羰基、式 -CHRa-（其中 Ra 是氢原子或低级烷基）或式 -NRb-（其中 Rb 是氢原子或低级烷基）、或X和Y共同形成乙烯基或乙炔基），条件是当X和Y中的一个是氧原子、硫原子或式-NRb-（其中Rb如上所定义）的基团时，另一个是羰基或式-CHRa-（其中Ra如上所定义）的基团，而W是卤素原子，以及制备此类化合物的工艺。
• 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：——
• Process for producing enyne derivatives
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0421302B1

  公开（公告）日：1996-06-26
• NUSSBAUMER, PETER;PETRANYI, GABOR;STUTZ, ANTON, J. MED. CHEM., 34,(1991) N, C. 65-73
  作者：NUSSBAUMER, PETER、PETRANYI, GABOR、STUTZ, ANTON

  DOI：——

  日期：——