4-bromo-3,-5-dimethyl-phenyl 3-phenylpropiolate | 267901-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-bromo-3,-5-dimethyl-phenyl 3-phenylpropiolate
• 英文别名: 3',5'-dimethyl-4'-bromophenyl phenylpropiolate；4-bromo-3,5-dimethylphenyl 3-phenylpropiolate；(4-bromo-3,5-dimethylphenyl) 3-phenylprop-2-ynoate
• CAS: 267901-42-8
• 化学式: C₁₇H₁₃BrO₂
• 分子量: 329.193
• InChiKey: REXUDXYQWDYAHI-UHFFFAOYSA-N

物化性质

• 沸点：
  428.0±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-3,-5-dimethyl-phenyl 3-phenylpropiolate 在 palladium diacetate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到6-bromo-5,7-dimethyl-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  Compounds for the treatment of mycobacterial infections

  摘要：

  本发明涉及式I化合物或其药用盐、酯或前药。

  公开号：

  US09416121B2
• 作为产物：
  描述：

  4-溴-3,5-二甲酚 、 苯丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以100%的产率得到4-bromo-3,-5-dimethyl-phenyl 3-phenylpropiolate
  参考文献：
  名称：

  Compounds for the treatment of mycobacterial infections

  摘要：

  本发明涉及式I化合物或其药用盐、酯或前药。

  公开号：

  US09416121B2

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT D'INFECTIONS MYCOBACTÉRIENNES
  申请人：BROAD INST INC

  公开号：WO2013049567A1

  公开（公告）日：2013-04-04

  The invention relates to compounds of Formula (I) or a pharmaceutically acceptable salt, ester or prodrug thereof and further relates to the use of a compound of Formula (I) for the treatment of a bacterial infection, in particular, mycobacterial infection. The compounds of the invention can be used for anti-mycobacterial activity against clinically sensitive as well as resistant strains of Mycobacterium tuberculosis.

  该发明涉及式（I）的化合物或其药学上可接受的盐、酯或前药，并进一步涉及使用式（I）的化合物治疗细菌感染，特别是分枝杆菌感染。该发明的化合物可用于对临床敏感和耐药分枝杆菌菌株的抗分枝杆菌活性。
• COMPOUNDS FOR THE TREATMENT OF MYCOBACTERIAL INFECTIONS
  申请人：Massachusetts General Hospital

  公开号：US20140296232A1

  公开（公告）日：2014-10-02

  The invention relates to compounds of Formula I or a pharmaceutically acceptable salt, ester or prodrug thereof:

  本发明涉及式I的化合物或其药学上可接受的盐、酯或前药：
• New Method for Preparation of Coumarins and Quinolinones via Pd-Catalyzed Intramolecular Hydroarylation of C−C Triple Bonds
  作者：Chengguo Jia、Dongguo Piao、Tsugio Kitamura、Yuzo Fujiwara

  DOI：10.1021/jo000861q

  日期：2000.11.1

  A new and general method has been developed for preparation of coumarins and quinolinones by intramolecular hydroarylation of alkynes. Various aryl alkynoates and alkynanilides undergo fast intramolecular reaction at room temperature in the presence of a catalytic amount of Pd(OAc)(2) in a mixed solvent containing trifluoroacetic acid (TFA), affording coumarins and quinolinones in moderate to excellent yields with more than 1000 turnover numbers (TON) to Pd. The methodology proved to tolerate a number of functional groups such as Br and CHO. On the basis of isotope experiments, a possible mechanism involving ethynyl chelation-assisted electrophilic metalation of aromatic C-H bonds by in-situ generated cationic Pd(II) species has been discussed. Also the involvement of vinylcationic species has been suggested.
• Synthesis and structure–activity relationships of phenyl-substituted coumarins with anti-tubercular activity that target FadD32
  作者：Tomohiko Kawate、Noriaki Iwase、Motohisa Shimizu、Sarah A. Stanley、Samantha Wellington、Edward Kazyanskaya、Deborah T. Hung

  DOI：10.1016/j.bmcl.2013.09.035

  日期：2013.11

  In an effort to develop new and potent agents for therapy against tuberculosis, a high-throughput screen was performed against Mycobacterium tuberculosis strain H37Rv. Two 6-aryl-5,7-dimethyl-4-phenylcoumarin compounds 1a and 1b were found with modest activity. A series of coumarin derivatives were synthesized to improve potency and to investigate the structure-activity relationship of the series. Among them, compounds 1o and 2d showed improved activity with IC90 of 2 mu M and 0.5 mu M, respectively. Further optimization provided compound 3b with better physiochemical properties with IC90 0.4 mu M which had activity in a mouse model of infection. The role of the conformation of the 4- and 6-aryl substituents is also described. (c) 2013 Elsevier Ltd. All rights reserved.
• Sequential Pd(II)−Pd(0) Catalysis for the Rapid Synthesis of Coumarins
  作者：Kelin Li、Yibin Zeng、Ben Neuenswander、Jon A. Tunge

  DOI：10.1021/jo050671l

  日期：2005.8.1

  Electrophilic palladium-catalyzed cycloisomerization of brominated aryl propiolates produces brominated coumarins. The brominated cournarins can be diversified by reduction of the Pd(II) catalyst to Pd(O) followed by Suzuki, Sonogashira, Heck, or Hartwig-Buchwald coupling. Thus, a single loading of precatalyst can be used to conduct sequential reactions, allowing the synthesis of functionalized coumarins. Extension of this methodology toward the synthesis of coumarin libraries is discussed.