(S)-N-benzhydrylidene-N'-[2.2]paracyclophane-4-yl-hydrazine

• 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: (S)-N-benzhydrylidene-N'-[2.2]paracyclophane-4-yl-hydrazine
• 英文别名: (S)-N-benzhydrylidene-N'-[2.2]paracyclophan-4-yl-hydrazine；(Sp)-N-([2.2]paracyclophanyl)benzophenone hydrazone；N-(benzhydrylideneamino)tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaen-5-amine
• 化学式: C₂₉H₂₆N₂
• 分子量: 402.539
• InChiKey: ZTYGGDYWDPKPHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-benzhydrylidene-N'-[2.2]paracyclophane-4-yl-hydrazine 在 盐酸 、 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 乙二醇 、 苯 为溶剂， 反应 29.0h， 生成 C₂₉H₃₀ClN₃
  参考文献：
  名称：

  Planar chiral indoles: synthesis and biological effects of the enantiomers

  摘要：

  The paracyclophanyl triflates (R)-4 and (S)-4, which were obtained from racemic precursors through enzymatic-kinetic resolution, could be employed as key intermediates for the synthesis of planar chiral [2.2](4.7)indoloparacyclophanes. Subjecting the double-layered test compounds (R)-8 and (S)-8 to in vitro ligand-binding experiments displayed stereoselective receptor recognition. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00558-4
• 作为产物：
  描述：

  (S_p)-4-amino[2.2]paracyclophane 在 tetrafluoroboric acid 、 sodium t-butanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.34h， 生成 (S)-N-benzhydrylidene-N'-[2.2]paracyclophane-4-yl-hydrazine
  参考文献：
  名称：

  Asymmetric β-Boration of α,β-Unsaturated N-Acyloxazolidinones by [2.2]Paracyclophane-Based Bifunctional Catalyst

  摘要：

  An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

  DOI：

  10.1021/ol302839d

文献信息

• Indoloparacyclophanes: Synthesis and Dopamine Receptor Binding of a Novel Arylbioisostere
  作者：Birgit Ortner、Reiner Waibel、Peter Gmeiner

  DOI：10.1002/1521-3773(20010401)40:7<1283::aid-anie1283>3.0.co;2-#

  日期：2001.4
• Discovery of dopamine D4 receptor antagonists with planar chirality
  作者：Fabrizio Sanna、Birgit Ortner、Harald Hübner、Stefan Löber、Nuska Tschammer、Peter Gmeiner

  DOI：10.1016/j.bmc.2013.01.065

  日期：2013.4

  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.