2-(4-diphenyl)-6,7-dihydro-5H-1,4-dithiepine | 869097-48-3

• 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-(4-diphenyl)-6,7-dihydro-5H-1,4-dithiepine
• 英文别名: 2-(4-phenylphenyl)-6,7-dihydro-5H-1,4-dithiepine
• CAS: 869097-48-3
• 化学式: C₁₇H₁₆S₂
• 分子量: 284.446
• InChiKey: ITXCOVPIGRPJRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-diphenyl)-6,7-dihydro-5H-1,4-dithiepine 在 双氧水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 2-Biphenyl-4-yl-6,7-dihydro-5H-[1,4]dithiepine 1,1,4,4-tetraoxide
  参考文献：
  名称：

  2,3-Dihydro-dithiin and -dithiepine-1,1,4,4-tetroxides: small molecule non-peptide antagonists of the human galanin hGAL-1 receptor

  摘要：

  The neuropeptide galanin modulates several physiological functions such as cognition, learning, feeding behavior, and depression, probably via the galanin 1 receptor(GAL-R1). Using an HTS assay based on I-125-human galanin binding to the human galanin-l receptor (hGAL-R1), we discovered a series of 1,4-dithiin and dithiipine-1,1,4,4-tetroxides that exhibited binding affinity IC50's to hGAL-R1 ranging from 190 to 2700 nM. Two of the dithiepin analogues, 7 and 23, behaved pharmacologically as hGAL-R1 antagonists in secondary assays involving adenylate cyclase activity and GTP binding to G-proteins. Analogues 7 and 23 were also active in functional assays involving galanin, reversing the inhibitory effect of galanin on acetylcholine (ACh) release in rat brain hippocampal slices and electrically-stimulated guinea pig ileum twitch. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00062-6
• 作为产物：
  描述：

  2-(biphenyl-4-yl)-2-methyl-1,3-dithiane 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二(甲基氨基)萘 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 2-(4-diphenyl)-6,7-dihydro-5H-1,4-dithiepine
  参考文献：
  名称：

  2,3-Dihydro-dithiin and -dithiepine-1,1,4,4-tetroxides: small molecule non-peptide antagonists of the human galanin hGAL-1 receptor

  摘要：

  The neuropeptide galanin modulates several physiological functions such as cognition, learning, feeding behavior, and depression, probably via the galanin 1 receptor(GAL-R1). Using an HTS assay based on I-125-human galanin binding to the human galanin-l receptor (hGAL-R1), we discovered a series of 1,4-dithiin and dithiipine-1,1,4,4-tetroxides that exhibited binding affinity IC50's to hGAL-R1 ranging from 190 to 2700 nM. Two of the dithiepin analogues, 7 and 23, behaved pharmacologically as hGAL-R1 antagonists in secondary assays involving adenylate cyclase activity and GTP binding to G-proteins. Analogues 7 and 23 were also active in functional assays involving galanin, reversing the inhibitory effect of galanin on acetylcholine (ACh) release in rat brain hippocampal slices and electrically-stimulated guinea pig ileum twitch. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00062-6

文献信息

• Chiral Phosphoric Acid Catalyzed Enantioselective Ring Expansion Reaction of 1,3-Dithiane Derivatives: Case Study of the Nature of Ion-Pairing Interaction
  作者：Feng Li、Toshinobu Korenaga、Taishi Nakanishi、Jun Kikuchi、Masahiro Terada

  DOI：10.1021/jacs.7b13274

  日期：2018.2.21

  expansion reaction of 1,3-dithiane derivatives catalyzed by chiral phosphoric acid (CPA). An unprecedented enantioselective 1,2-sulfur rearrangement/stereospecific nucleophilic addition sequence was proven to be the stereoselective pathway. More importantly, by thorough investigation of the intrinsic nature of the stereospecific nucleophilic addition to the cationic thionium intermediate, we discovered

  近年来，通过离子对相互作用的手性反离子控制的不对称催化引起了极大的关注。尽管有许多成功的研究，但很少进行离子对相互作用中立体控制元件的机理阐明，因此其性质仍远未得到很好的理解。在此，我们报告了一项新开发的手性磷酸 (CPA) 催化的 1,3-二噻烷衍生物的对映选择性扩环反应的深入机理案例研究。史无前例的对映选择性 1,2-硫重排/立体特异性亲核加成序列被证明是立体选择性途径。更重要的是，通过彻底研究立体有择亲核加成到阳离子硫中间体的内在性质，我们发现该过程中的关键相互作用是CPA催化剂的共轭碱与阳离子中间体之间形成的非经典CH···O氢键。这些 CH···O 氢键不仅将催化剂与底物结合以在整个过程中形成能量有利的状态，而且还牢固地保持这些碎片的相对位置作为“固定”接触离子对，以维持在最初的硫重排步骤。这个机械案例研究提供了对有机催化中离子对相互作用性质的非常清楚的理解。该结论鼓励研究领域的
• Facile synthesis of substituted dihydro-1,4-dithiins and -1,4-dithiepins from α-oxo ketene cyclic dithioacetals
  作者：Dewen Dong、Ran Sun、Haifeng Yu、Yan Ouyang、Qian Zhang、Qun Liu

  DOI：10.1016/j.tetlet.2005.08.128

  日期：2005.10

  A novel and facile synthesis of substituted 2,3-dihydro-1,4-dithiins and 6,7-dihydro-5H-1,4-dithiepins based on the reactions of α-bromo/hydroxy ketones with α-oxo ketene cyclic dithioacetals has been developed. A general mechanism for the reactions is proposed.

  基于α-溴/羟基酮与α-氧代乙烯酮环的反应，可轻松合成新颖的取代的2,3-二氢-1,4-二硫辛和6,7-二氢-5 H -1,4-二硫平已开发出二硫缩醛。提出了反应的一般机理。