1-([2.2]paracyclophane-4-yl)-1H-pyrazole | 1428672-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-([2.2]paracyclophane-4-yl)-1H-pyrazole
• CAS: 1428672-38-1；1428672-39-2；1436384-67-6
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: LVDDSLIBCYTIPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-([2.2]paracyclophane-4-yl)-1H-pyrazole 在 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 三氯氧磷 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 (R)-1-(1-[2.2]paracyclophane-4-yl-1H-pyrazol-4-ylmethyl)-4-phenyl-piperazine
  参考文献：
  名称：

  Discovery of dopamine D4 receptor antagonists with planar chirality

  摘要：

  Employing the D-4 selective phenylpiperazine 2 as a lead compound, planar chiral analogs with paracyclophane substructure were synthesized and evaluated for their ability to bind and activate dopamine receptors. The study revealed that the introduction of a [2.2]paracyclophane moiety is tolerated by dopamine receptors of the D-2 family. Subtype selectivity for D-4 and ligand efficacy depend on the absolute configuration of the test compounds. Whereas the achiral single-layered lead 2 and the double-layered paracyclophane (R)-3 showed partial agonist properties, the enantiomer (S)-3 behaved as a neutral antagonist. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.065
• 作为产物：
  描述：

  1,1,3,3-四甲氧基丙烷 、 (S)-N-benzhydrylidene-N'-[2.2]paracyclophane-4-yl-hydrazine 在 盐酸 、 对甲苯磺酸 、 乙二醇 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 19.5h， 以77%的产率得到1-([2.2]paracyclophane-4-yl)-1H-pyrazole
  参考文献：
  名称：

  Discovery of dopamine D4 receptor antagonists with planar chirality

  摘要：

  Employing the D-4 selective phenylpiperazine 2 as a lead compound, planar chiral analogs with paracyclophane substructure were synthesized and evaluated for their ability to bind and activate dopamine receptors. The study revealed that the introduction of a [2.2]paracyclophane moiety is tolerated by dopamine receptors of the D-2 family. Subtype selectivity for D-4 and ligand efficacy depend on the absolute configuration of the test compounds. Whereas the achiral single-layered lead 2 and the double-layered paracyclophane (R)-3 showed partial agonist properties, the enantiomer (S)-3 behaved as a neutral antagonist. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.065

文献信息

• Synthesis and characterization of phosphorescent cyclometalated Ir and Pt heteroleptic complexes using cyclophane-based chelates
  作者：B.K. Thilini Batagoda、Peter I. Djurovich、Stefan Bräse、Mark E. Thompson

  DOI：10.1016/j.poly.2016.04.039

  日期：2016.9

  racemates due to the planar chirality of the cyclophane ring system. Two diastereomers of (pCpz)2Ir(acac), one with C1 symmetry (ΛRS, ΔSR) and the other with C2 symmetry (ΛRR, ΔSS) were isolated, whereas only one C1 diastereomer was obtained for (pCpy)2Ir(acac). Inherent strain in the cyclophane core and transannular interaction between the bridged phenyl rings leads to a 250–400 mV cathodic shift in the

  摘要报道了一系列含有环烷取代的螯合物的中性环金属化的Pt（II）和Ir（III）杂配物的合成与表征。该配合物的通式为（C ^ N）Pt（O ^ O）或（C ^ N）2Ir（O ^ O），其中C ^ N为单阴离子环烷配体2-（[[2.2]-对环环-4- yl）吡啶基（pCpy）或1-（[2.2]-对环烷-4-基）吡唑基（pCpz），（O 2 O）是辅助配体；乙酰丙酮酸（acac）或二甲苯基甲烷（dpm）。由于环烷环系统的平面手性，获得了pCpyH和pCpzH配体前体为外消旋体。分离了（pCpz）2Ir（acac）的两个非对映异构体，一个具有C1对称性（ΛRS，ΔSR），另一个具有C2对称性（ΛRR，ΔSS），而对于（pCpy）2Ir（acac）仅获得一个C1非对映体。相对于与ppy或ppz配体的类似络合物，环烷核的固有应变和桥联苯环之间的跨环相互作用导致氧化电位发生250-400 mV阴极移
• Palladium-Catalyzed CH Bond Acetoxylation: An Approach to<i>ortho</i>-Substituted Hydroxy[2.2]paracyclophane Derivatives
  作者：Petra Lennartz、Gerhard Raabe、Carsten Bolm

  DOI：10.1002/adsc.201200625

  日期：2012.11.26

  The palladium-catalyzed direct CH bond acetoxylation of [2.2]paracyclophanes has been investigated. Various mono- and disubstituted [2.2]paracyclophanes were subjected to typical Sanford acetoxylation conditions. Oxime ethers, an oxime acetate, a pyridine, and a pyrazole with [2.2]paracyclophane cores underwent direct ortho-acetoxylation in good to excellent yields using 1–5 mol% of palladium(II) acetate

  研究了钯催化的[2.2]对环环烷的直接CH键乙酰氧基化。各种单取代和双取代的[2.2]对环环烷都要经受典型的Sanford乙酰氧基化条件。肟醚，肟酯，吡啶，并用[2.2]对环芳烷核后行直接吡唑邻良好乙酰氧基化，以优异的产率与二乙酸碘苯作为氧化剂组合使用1-5摩尔％的钯（II）乙酸盐。该反应可以在数克范围内进行，并且邻-乙酰氧基化的[2.2]对环环烷适于进一步官能化，从而提供羟基[2.2]对环环烷衍生物和平面手性苯并恶唑。