2-fluoro-2'-methylbiphenyl | 80254-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-2'-methylbiphenyl
• 英文别名: 2-fluoro-2'-methyl-1,1'-biphenyl；1-fluoro-2-(2-methylphenyl)benzene
• CAS: 80254-69-9
• 化学式: C₁₃H₁₁F
• mdl: MFCD06802478
• 分子量: 186.229
• InChiKey: MSFNHNJJLZRLEX-UHFFFAOYSA-N

物化性质

• 沸点：
  252.0±9.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-fluoro-2'-methylbiphenyl 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.08h， 生成 9-(2''''-Fluoro-biphenyl-2-ylmethyl)-6-(4-nitro-benzylsulfanyl)-9H-purine
  参考文献：
  名称：

  Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine:  Replacement of the Ribose Moiety by Substituted Benzyl Groups

  摘要：

  4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogues gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the phenyl group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, K-i values in the low nanomolar range were obtained for the benzyl-substituted derivatives. Compound 35, LUF5919, and compound 60, LUF5929, displayed the highest affinity (K-i = 39 nM for both compounds), having a polar surface area of 101 Angstrom(2) and 85 Angstrom(2), respectively.

  DOI：

  10.1021/jm049735v
• 作为产物：
  描述：

  2-溴氯苯 、 2-溴甲苯 在 magnesium 、 lithium chloride 、 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 2.0h， 以61%的产率得到2-fluoro-2'-methylbiphenyl
  参考文献：
  名称：

  一种新的实用的格氏偶联-氟化序列：2-芳基氟芳烃的合成

  摘要：

  已经开发了合成2-芳基和2-杂芳基氟代芳烃的新策略。在温和条件下，分子间的多米诺骨牌格氏耦合-氟化序列提供了一系列来自芳基溴化物的2-氟联芳基。这种方法可以进一步扩展到2'-芳基-2-氟联苯的合成。

  DOI：

  10.1002/asia.201000288

文献信息

• 3-HETEROARYL (AMINO OR AMIDO)-1-(BIPHENYL OR PHENYLTHIAZOLYL) CARBONYLPIPERIDINE DERIVATIVES AS OREXIN RECEPTOR INHIBITORS
  申请人：Aissaoui Hamed

  公开号：US20100069418A1

  公开（公告）日：2010-03-18

  The invention relates to piperidine compounds of formula (I) wherein X-R 1 represents —N(H)-pyrimidinyl, wherein said pyrimidinyl is unsubstituted or mono-substituted wherein the substituent is selected from (C 1-4 )alkyl or halogen, or X-R 1 represents —NH—C(O)-heterocyclyl, wherein the heterocyclyl is selected from benzofuranyl and imidazo[2,1-b]-thiazolyl, wherein said heterocyclyl is unsubstituted or independently mono-, di-, or tri-substituted wherein the substituents are independently selected from (C 1-4 )alkyl; A represents a phenyl- or thiazolyl-group, wherein the phenyl or thiazolyl is unsubstituted or mono-substituted with (C 1-4 )alkyl; B represents a phenyl-group, wherein the phenyl is unsubstituted or mono-, or di-substituted, wherein the substituents are independently selected from the group consisting of (C 1-4 )alkyl, (C 1-4 )alkoxy, trifluoromethyl, cyano and halogen; to pharmaceutically acceptable salts thereof, and to the use of such compounds use as medicaments, especially as orexin receptor antagonists.

  该发明涉及式（I）的哌啶化合物，其中X-R1代表-N(H)-嘧啶基，其中所述的嘧啶基未取代或单取代，取代基选自（C1-4）烷基或卤素，或者X-R1代表-NH-C(O)-杂环基，其中所述的杂环基选自苯并呋喃基和咪唑[2,1-b]-噻唑基，其中所述的杂环基未取代或独立单取代、双取代或三取代，取代基独立选自（C1-4）烷基；A代表苯基或噻唑基，其中所述的苯基或噻唑基未取代或单取代为（C1-4）烷基；B代表苯基，其中所述的苯基未取代或单取代、双取代，取代基独立选自（C1-4）烷基、（C1-4）烷氧基、三氟甲基、氰基和卤素；以及其药学上可接受的盐，以及将这类化合物用作药物，特别是用作促觉醒素受体拮抗剂。
• An easily prepared, air and moisture stable, resin-bound palladium catalyst for Suzuki cross-coupling reactions
  作者：Tony Y. Zhang、Matthew J. Allen

  DOI：10.1016/s0040-4039(99)01147-8

  日期：1999.8

  An air and moisture stable polymer supported palladium catalyst easily prepared from a commercial available thiourea resin Deloxan®THP was found to enable Suzuki cross-coupling reactions to be carried out in high yields and convenient manner.

  从商业可用的硫脲树脂DELOXAN容易制备的空气和湿气稳定的聚合物载体上的钯催化剂® THP被发现使Suzuki交叉偶联反应中，被以高产率和方便的方式进行。
• 3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES
  申请人：Aissaoui Hamed

  公开号：US20100016401A1

  公开（公告）日：2010-01-21

  The invention relates to 3-aza-bicyclo[3.1.0]hexane derivatives of formula (I) wherein A, B, n, X, and R 1 are as described in the description, and salts thereof, and their use as orexin receptor antagonists.

  这项发明涉及式(I)的3-aza-双环[3.1.0]己烷衍生物，其中A、B、n、X和R1如描述中所述，以及其盐，以及它们作为促进睡眠的荷尔蒙受体拮抗剂的用途。
• An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki–Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids
  作者：Shin Ando、Hirofumi Matsunaga、Tadao Ishizuka

  DOI：10.1021/acs.joc.6b02666

  日期：2017.1.20

  A nickel half-sandwich complex supported by our original NHC ligand was developed as a robust precatalyst for Suzuki–Miyaura cross-coupling. The addition of PPh3 was a crucial element in the suppression of side reactions and in accelerating the cross-coupling reaction. By employing the optimal conditions, aryl–aryl, heteroaryl–aryl, and heteroaryl–heteroaryl couplings were achieved.

  我们最初的NHC配体支持的镍半三明治复合物被开发为铃木-宫浦交叉偶联的强力预催化剂。PPh 3的添加对于抑制副反应和加速交叉偶联反应至关重要。通过采用最佳条件，可以实现芳基-芳基，杂芳基-芳基和杂芳基-杂芳基偶联。
• C(sp²)–H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities
  作者：Jennifer V. Obligacion、Máté J. Bezdek、Paul J. Chirik

  DOI：10.1021/jacs.6b13346

  日期：2017.2.22

  Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp2)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-(iPrPNP)Co(H)2BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-(iPrPNP)Co(O2CtBu)2 (2) compounds were effective and exhibited broad functional

  已经开发出具有电子增强位点选择性的钴催化剂，在氟化芳烃的 C(sp2)-H 硼酸化中观察到的高邻位氟选择性证明了这一点。空气敏感的二氢化钴 (III) 硼基 4-Me-(iPrPNP)Co(H)2BPin (1) 和空气稳定的钴 (II) 双（新戊酸盐）4-Me-(iPrPNP)Co(O2CtBu) 2 (2) 化合物是有效的，并且在包含电子不同官能团的各种氟芳烃中表现出广泛的官能团耐受性，而不管芳烃上的取代模式如何。在苄基二甲胺和氢硅烷存在的情况下，钴催化剂观察到的电子增强的邻氟选择性得以保持，超过了贵金属催化剂观察到的已建立的定向基团效应。