5-bromo-2-(5-chloro-2-thienyl)pyridine | 183619-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-bromo-2-(5-chloro-2-thienyl)pyridine
• 英文别名: 5-Bromo-2-(5-chlorothiophen-2-yl)pyridine
• CAS: 183619-09-2
• 化学式: C₉H₅BrClNS
• 分子量: 274.568
• InChiKey: LNXZPHRNZWOEDN-UHFFFAOYSA-N

物化性质

• 沸点：
  330.1±37.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(5-chloro-2-thienyl)pyridine 在 叔丁基锂 、 二氧化硫 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 6-(5-chloro-2-thienyl)-3-pyridinesulfonyl chloride
  参考文献：
  名称：

  Factor Xa Inhibitors:  S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides

  摘要：

  Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.

  DOI：

  10.1021/jm060870c
• 作为产物：
  描述：

  5-chloro-2-thienylzinc bromide 、 2,5-二溴吡啶 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到5-bromo-2-(5-chloro-2-thienyl)pyridine
  参考文献：
  名称：

  A Study on the Selectivity of Arylzinc Reagents in Cross-coupling Reactions with Chemically Equivalent and Pseudo-equivalent Dibromopyridines

  摘要：

  DOI：

  10.5012/bkcs.2014.35.1.280

文献信息

• π-Conjugated Donor−Acceptor Copolymers Constituted of π-Excessive and π-Deficient Arylene Units. Optical and Electrochemical Properties in Relation to CT Structure of the Polymer
  作者：Takakazu Yamamoto、Zhen-hua Zhou、Takaki Kanbara、Masaki Shimura、Kenichi Kizu、Tsukasa Maruyama、Yoshiyuki Nakamura、Takashi Fukuda、Bang-Lin Lee、Naoki Ooba、Satoru Tomaru、Takashi Kurihara、Toshikuni Kaino、Kenji Kubota、Shintaro Sasaki

  DOI：10.1021/ja961550t

  日期：1996.1.1

  Various π-conjugated copolymers constituted of π-excessive thiophene, selenophene, or furan units (Ar) and π-deficient pyridine or quinoxaline (Ar‘) units have been prepared in high yields by the following organometallic polycondensation methods: (i) n X−Ar−Ar‘−X + n Ni(0)Lm → (-Ar−Ar‘)-n (X = halogen, Ni(0)Lm = zerovalent nickel complex), (ii) n X−Ar−X + n Me3Sn−Ar‘−SnMe3 → (-Ar−Ar‘)-n (palladium

  由 π-过量噻吩、硒吩或呋喃单元 (Ar) 和 π-缺陷吡啶或喹喔啉 (Ar') 单元构成的各种 π-共轭共聚物已通过以下有机金属缩聚方法以高产率制备： (i) n X −Ar−Ar'−X + n Ni(0)Lm → (-Ar−Ar')-n (X = 卤素，Ni(0)Lm = 零价镍络合物)，(ii) n X−Ar−X + n Me3Sn−Ar'−SnMe3 → (-Ar−Ar')-n（钯催化），和 (iii) a X−Ar−X + b X−Ar'−X + (a + b)Ni(0) Lm → (-Ar)x(Ar')-y。粉末X射线衍射分析证实了通过方法ii制备的聚合物的替代结构。该共聚物的分子量为 5.4 × 103 至 3.3 × 105，[η] 值为 0.37 至 4.4 dL g-1。共聚物的 π−π* 吸收带通常显示出相对于相应均聚物 (-Ar)-n 和 (-Ar')-n 的红移，并且红移是由共聚物的电荷转移
• Factor Xa Inhibitors:  S1 Binding Interactions of a Series of <i>N</i>-{(<i>3S</i>)-1-[(<i>1S</i>)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides
  作者：Chuen Chan、Alan D. Borthwick、David Brown、Cynthia L. Burns-Kurtis、Matthew Campbell、Laiq Chaudry、Chun-wa Chung、Máire A. Convery、J. Nicole Hamblin、Lisa Johnstone、Henry A. Kelly、Savvas Kleanthous、Angela Patikis、Champa Patel、Anthony J. Pateman、Stefan Senger、Gita P. Shah、John R. Toomey、Nigel S. Watson、Helen E. Weston、Caroline Whitworth、Robert J. Young、Ping Zhou

  DOI：10.1021/jm060870c

  日期：2007.4.1

  Factor Xa inhibitory activities for a series of N-(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.
• A Study on the Selectivity of Arylzinc Reagents in Cross-coupling Reactions with Chemically Equivalent and Pseudo-equivalent Dibromopyridines
  作者：Hye-Soo Jung、Seung-Hoi Kim

  DOI：10.5012/bkcs.2014.35.1.280

  日期：2014.1.20