3-(4-butoxyphenyl)pyrazole | 192573-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-butoxyphenyl)pyrazole
• 英文别名: 3-(4-n-butoxyphenyl)pyrazole；3-(4-(butoxy)phenyl)-1H-pyrazole；5-(4-Butoxy-phenyl)-1H-pyrazole；5-(4-butoxyphenyl)-1H-pyrazole
• CAS: 192573-75-4
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: TVVGACWXAKCONN-UHFFFAOYSA-N

物化性质

• 熔点：
  72-76 °C
• 沸点：
  399.8±25.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(norbornadiene)rhodium(I)chloride]2 、 3-(4-butoxyphenyl)pyrazole 以 二氯甲烷 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  3- [4-苯氧基苯基]吡唑的铑化学晶体结构中的3- [4-苯氧基苯基]吡唑（Hpz pp）和3- [4-丁氧基苯基]吡唑（Hpz bp）， 含有3- [4-苯氧基苯基]（pp）和3- [4-丁氧基苯基]（bp）取代基的新型吡唑Hpzpp和Hpz bp，已经合成和表征，并且还报道了3- [4-苯氧苯基]吡唑（Hpz pp）的晶体结构。

  摘要：

  The novel pyrazoles containing 3-[4-phenoxyphenyl] (pp) and 3-[4-butoxyphenyl] (bp) substituents, Hpz(pp) and Hpz(bp), have been synthetized and characterized, and the crystalline structure of 3-[4-phenoxiphenyl]pyrazole (Hpa(pp)) is also reported.Rh(I) compounds [Rh(Cl)(Hpz(R))(LL)] and [Rh(mu-pz(R))(LL)](2) (LL = NBD, COD, 2CO; R = pp, bp) have been prepared in order to explore the influence of the alkoxy- or aryloxyphenyl substituents on the pyrazol ring of some features such as the presence of dynamic processes or the preference of determined isomers in the complexes.The molecular structures of complexes [Rh(Cl)(Hpz(R))(LL)] and [Rh(mu-pz(R))(LL)](2) (LL = NBD, COD, 2CO; R = pp, bp) have been studied by IR and H-1 and C-13 NMR spectroscopies.H-1 NMR spectra of compounds [Rh(Cl)(Hpz(R))(LL)] (LL = NBD, COD, 2CO; R = pp, bp) indicate that the presence of a metallotropic equilibrium only depends on the steric characteristics of the ancillary ligands.On the other hand, complexes [Rh(mu-pz(R))(CO)(2)](2) (R = pp, bp) are formed as a mixture of the head-to-head (H-H) and head-to-tail (H-T) configurational isomers. By contrast, [Rh(mu-pz(R))(LL)](2) (LL = NBD, COD; R = pp, bp) have been obtained as only one isomer in both the solid state and the solution. The crystalline structures of complexes [Rh(mu-pz(pp))(COD)](2) . 1/2CH(2)Cl(2) and [Rh(mu-pz(bp))(COD)](2) have been solved, showing the presence of the H-T configurational isomer in both cases.The H-1 NMR spectra of [Rh(mu-pz(R))(LL)](2) (LL = NBD, COD, 2CO; R = pp, bp) show that the ortho protons of the C6H4 group of the substituents on the pyrazol ring are considerably deshielded. Furthermore, the X-ray structures of [Rh(mu-pz(pp))(COD)](2) . 1/2CH(2)Cl(2) and [Rh(mu-pz(bp))(COD)](2) complexes show an Rh-H(ortho) distance of ca. 2.7 Angstrom, characteristic of a weak preagostic interaction.

  DOI：

  10.1016/s0022-328x(96)06890-8
• 作为产物：
  描述：

  4-(正丁氧基)苯乙酮 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 3-(4-butoxyphenyl)pyrazole
  参考文献：
  名称：

  Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors

  摘要：

  In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation of HET0016 was limited by its poor solubility under neutral conditions and instability under acidic conditions. The instability of HET0016 in acidic conditions is due to the N-hydroxyformamidine moiety, which is considered to be essential for the potent and selective activity seen in our previous study. The activity was maintained when the N-hydroxyformamidine moiety was replaced by an imidazole ring (3a; IC50 = 5.7 +/- 1.0 nM), but this was associated with a loss of selectivity for cytochrome P450s (CYPs). However, other azole derivatives such as isoxazole derivative 23 (IC50 value 38 +/- 10 nM) and pyrazole derivative 24 (IC50 value 23 +/- 12 nM) showed potent and selective activities with improved stability.

  DOI：

  10.1021/jm020557k

文献信息

• Cationic Silver Coordination Compounds of Polydentate Ligands: Supramolecular Structures of [Ag(Pz ^bp2 Py) ₂ (OSO ₂ CF ₃ )] and [Ag ₂ (Pz ^bp2 Py) ₂ (OSO ₂ CF ₃ ) ₂ ] {Pz ^bp2 Py = 2‐[3,5‐Bis(4‐butoxyphenyl)pyrazol‐1‐yl]pyridine}
  作者：M. Luz Gallego、Mercedes Cano、José A. Campo、José V. Heras、Elena Pinilla、M. Rosario Torres、Pilar Cornago、Rosa M. Claramunt

  DOI：10.1002/ejic.200500231

  日期：2005.11

  The new silver complexes [Ag(Pz b p 2 Py) 2 (OSO 2 CF 3 )], [Ag 2 (Pz b p 2 Py) 2 (OSO 2 CF 3 ) 2 ], [Ag(Pz b p Py) 2 (OSO 2 CF 3 )], [Ag 3 -(TPz b p 2 Tz)(OSO 2 CF 3 ) 3 ] and [Ag 3 (TPz b p PTz)(OSO 2 CF 3 ) 3 ] (5-9) have been obtained by reaction of Ag(OSO 2 CF 3 ) with the corresponding polydentate ligand 2-[3,5-bis(4-butoxyphenyl)pyrazol-l-yl]pyridine (Pz b p 2 Py, 1), 2-[3-(4-butoxyphenyl)pyrazol1-yl]pyridine

  新的银络合物[Ag(Pz bp 2 Py) 2 (OSO 2 CF 3 )]、[Ag 2 (Pz bp 2 Py) 2 (OSO 2 CF 3 ) 2 ]、[Ag(Pz bp Py) 2 (OSO) 2 CF 3 )]、[Ag 3 -(TPz bp 2 Tz)(OSO 2 CF 3 ) 3 ] 和[Ag 3 (TPz bp PTz)(OSO 2 CF 3 ) 3 ] (5-9) 由Ag(OSO 2 CF 3 ) 与相应的多齿配体 2-[3,5-双(4-丁氧基苯基)吡唑-1-基]吡啶 (Pz bp 2 Py, 1), 2-[3-(4) 的反应-丁氧基苯基）吡唑1-基]吡啶（Pz bp Py，2），2,4,6-三[3,5-双（4-丁氧基苯基）吡唑-1-基]-l,3,5-三嗪（TPz bp 2 Tz, 3) 和 2,4,6-tris[3-(4-butoxyphenyl)pyrazol-1-yl]-1
• Silver and gold luminescent metallomesogens based on pyrazole ligands
  作者：María José Mayoral、Paloma Ovejero、José Antonio Campo、José Vicente Heras、Elena Pinilla、María Rosario Torres、Carlos Lodeiro、Mercedes Cano

  DOI：10.1039/b808487d

  日期：——

  A series of ionic bis(pyrazole)-silver(I) and -gold(I) complexes [ML2][A] (M = Ag, Au; A = BF4−, PF6−, NO3−), prepared by coordination of the mesomorphic L = Hpz2R(n) or non-mesomorphic L = HpzR(n) pyrazole ligands (Hpz2R(n) = 3,5-bis(4-alkyloxyphenyl)pyrazole; HpzR(n) = 3-(4-alkyloxyphenyl)pyrazole), has been studied. The complexes exhibit enantiotropic behaviour, showing smectic A (SmA) mesophases. The choice of the ligands allows the achievement of ‘H’ or ‘U’ molecular shapes, which appear to be responsible for the attainment of liquid crystal mesophases, these not being dependent on the coordinating or non-coordinating nature of the A counteranions. The new complexes are photoluminescent both in the solid state and in solution at room temperature. In addition, the luminescent behaviour of selected compounds as a function of the temperature indicates that the luminescence is maintained in the mesophase.

  一系列离子型双（吡唑）-银（I）和-金（I）配合物[ML2][A]（M = Ag, Au；A = BF4-、PF6-、NO3-）配位制备的中形态 L = Hpz2R(n) 或非中形态 L = HpzR(n) 吡唑配体（Hpz2R(n) = 3,5-双(4-烷氧基苯基)吡唑；HpzR(n) = 3-(4-烷氧基苯基)吡唑）。这些配合物表现出各向异性，呈现出 Smectic A (SmA) 介相。配体的选择可以实现 "H "或 "U "分子形状，这似乎是实现液晶介相的原因，而这些并不取决于 A 反阳离子的配位或非配位性质。在室温下，这些新复合物在固态和溶液中都能发光。此外，所选化合物的发光行为与温度的函数关系表明，发光在介相中得以保持。
• Silver and Gold Trinuclear Complexes Based on 3-Substituted or 3,5-Disubstituted Pyrazolato Ligands. X-Ray Crystal Structure ofcyclo-Tris{μ-[3,5-bis(4-phenoxyphenyl)-1H-pyrazolato-κN1 : κN2]}trigold Dichloromethane ([Au(μ-)]3⋅CH2Cl2)
  作者：M. Carmen Torralba、Paloma Ovejero、M. José Mayoral、Mercedes Cano、José A. Campo、José V. Heras、Elena Pinilla、M. Rosario Torres

  DOI：10.1002/hlca.200490012

  日期：2004.1

  mesophases that could be related to the disc-like shape of the molecular core and the appropriate length of the alkyloxy chain. For comparative purposes, the X-ray structure of the related gold complex [Au3(μ-)3] (9) having phenoxyphenyl substituents at the 3- and 5-positions of the pyrazolato ligand is also described. The molecular structure is formed by a non-planar (AuNN)3 core, containing three Au-atoms

  [M 3（μ- PZ'）3 ]类型的十个新的银和金三聚体配合物（M = Au，Ag），其中PZ'表示衍生自介晶3,5-二取代1 H-吡唑或非-合成并表征了介晶的3-取代的1 H-吡唑HPZ R（R = C 6 H 4 OC n H 2 n +1）。金和银络合物7，8，10，和11含有对称pyrazolato配体作为桥连基团（; R = C 6 H ^ 4 OC ñ ħ 2 Ñ+1，n = 4（）和8（））表现出三角对称结构。用于相关银衍生物得到相同的结果16 - 18 3 -取代的pyrazolato配体（PZ - [R ; R = C 6 H ^ 4 OC ñ ħ 2 Ñ 1，Ñ = 4（PZ BP），12（PZ DDP） ，以及18（PZ odp））。相比之下，3-取代的吡唑并金化合物13 – 15所采用的不对称分子结构与三核核上的取代基的位置有关。通过差示扫描量热法和偏振光显微镜研究了这些配合物的热行为。父3
• METHODS OF MODULATING CELL PROLIFERATION AND CYST FORMATION IN POLYCYSTIC KIDNEY AND LIVER DISEASES
  申请人：The Medical College of Wisconsin, Inc.

  公开号：EP2061450B1

  公开（公告）日：2017-04-19
• Methods of modulating cell proliferation and cyst formation in polycystic kidney and liver diseases
  申请人：Sweeney William E.

  公开号：US20080167382A1

  公开（公告）日：2008-07-10

  The present invention provides a method for preferentially reducing the proliferation of cystic epithelial cells in the kidney or bile duct in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to preferentially reduce the proliferation of cystic epithelial cells over normal epithelial cells such as tubule epithelial cells in the kidney or bile duct. The present invention also provides a method for preventing or treating autosomal dominant polycystic kidney disease (ADPKD), autosomal recessive polycystic kidney disease (ARPKD), ARPKD associated congenital hepatic fibrosis, ARPKD associated Caroli's disease, or cholangiocarcinoma in a mammal in need thereof by administering a 20-HETE synthesizing enzyme inhibitor or a 20-HETE antagonist to the mammal in an amount sufficient to prevent or treat the disease.