4-(2-chloropyrimidin-5-yl)phenol | 554453-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-chloropyrimidin-5-yl)phenol
• 英文别名: 4-(2-Chloro-5-pyrimidinyl)phenol
• CAS: 554453-84-8
• 化学式: C₁₀H₇ClN₂O
• 分子量: 206.631
• InChiKey: KIYDSMOBCOJJKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chloropyrimidin-5-yl)phenol 在 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 mineral oil 为溶剂， 生成 [Dimethyl(trimethylsilylmethyl)silyl]methyl-[11-[5-(4-hexoxyphenyl)pyrimidin-2-yl]oxyundecyl]-dimethylsilane
  参考文献：
  名称：

  Design of liquid crystals with ‘de Vries-like’ properties: carbosilane-terminated 5-phenylpyrimidine mesogens suitable for chevron-free FLC formulations

  摘要：

  碳硅烷终止的5-苯基嘧啶向列液晶在“de Vries-like”液晶中名列前茅。

  DOI：

  10.1039/c4tc00393d
• 作为产物：
  描述：

  2-chloro-5-(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)pyrimidine 在 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以99%的产率得到4-(2-chloropyrimidin-5-yl)phenol
  参考文献：
  名称：

  Design of liquid crystals with ‘de Vries-like’ properties: carbosilane-terminated 5-phenylpyrimidine mesogens suitable for chevron-free FLC formulations

  摘要：

  碳硅烷终止的5-苯基嘧啶向列液晶在“de Vries-like”液晶中名列前茅。

  DOI：

  10.1039/c4tc00393d

文献信息

• Simple microwave-assisted ligand-free suzuki cross-coupling: Functionalization of halo-pyrimidine moieties
  作者：Matteo Colombo、Marco Giglio、Ilaria Peretto

  DOI：10.1002/jhet.5570450420

  日期：2008.7

  An advantageous ligand-free protocol for Suzuki couplings is described. The synthetic procedure entails microwave irradiation for the reduction of the reaction times and the use of silica cartridges for the purification. Dihalo-pyrimidine structures, interesting scaffolds in medicinal chemistry, were chosen as test compounds.

  描述了用于铃木偶联的有利的无配体方案。合成过程需要微波辐射以缩短反应时间，并使用硅胶柱进行纯化。选择了在药物化学中令人感兴趣的支架二卤代嘧啶结构作为测试化合物。
• Electroclinic effect in a chiral carbosilane-terminated 5-phenylpyrimidine liquid crystal with ‘de Vries-like’ properties
  作者：Christopher P. J. Schubert、Carsten Müller、Michael D. Wand、Frank Giesselmann、Robert P. Lemieux

  DOI：10.1039/c5cc05212b

  日期：——

  The chiral carbosilane-terminated liquid crystal 2-[(2S,3S)-2,3-difluorohexyloxy]-5-[4-(12,12,14,14,16,16-hexamethyl-12,14,16-trisilaheptadecyloxy)phenyl]pyrimidine (QL32-6) undergoes a smectic A*-smectic C* phase transition with a maximum layer contraction of only 0.2%.

  手性碳硅烷端液晶2-[(2S,3S)-2,3-二氟己氧基]-5-[4-(12,12,14,14,16,16-六甲基-12,14,16-三硅十七烷氧基)苯基]嘧啶（QL32-6）发生了一个仅有0.2%的最大层收缩的斯米克A*-斯米克C*相变。
• Synthesis and biological activities of novel β-Carbolines as PDE5 inhibitors
  作者：Zhihua Sui、Jihua Guan、Mark J. Macielag、Weiqin Jiang、Yuhong Qiu、Patricia Kraft、Sheela Bhattacharjee、T.Matthew John、Elizabeth Craig、Donna Haynes-Johnson、Joanna Clancy

  DOI：10.1016/s0960-894x(02)01036-3

  日期：2003.2

  A series of N-2-furoyl and N(2)pyrimidinyl beta-carbolines was discovered to possess potent inhibitors activity against PDE5. During the synthesis we developed a tandem resin quenching protocol. which allowed us to synthesize large number of target compounds in a rapid fashion. Representative Compounds exhibit superior selectivity to sildenafil versus other isozymes of PDEs. and demonstrated in vivo efficacy in increasing introcavernosal pressure in dogs. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Design of liquid crystals with ‘de Vries-like’ properties: carbosilane-terminated 5-phenylpyrimidine mesogens suitable for chevron-free FLC formulations
  作者：Christopher P. J. Schubert、Andreas Bogner、Jan H. Porada、Khurshid Ayub、Tamer Andrea、Frank Giesselmann、Robert P. Lemieux

  DOI：10.1039/c4tc00393d

  日期：——

  Carbosilane-terminated 5-phenylpyrimidine mesogens rank among the best ‘de Vries-like’ liquid crystals.

  碳硅烷终止的5-苯基嘧啶向列液晶在“de Vries-like”液晶中名列前茅。