4,5-dimethylbenzenediazonium-2-carboxylate hydrochloride | 39654-49-4

• 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: 4,5-dimethylbenzenediazonium-2-carboxylate hydrochloride
• CAS: 39654-49-4
• 化学式: C₉H₈N₂O₂*ClH
• 分子量: 212.636
• InChiKey: DKRAFCBWHCPLFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6,6-hexamethylcyclohexa-2,4-dien-1-one 、 4,5-dimethylbenzenediazonium-2-carboxylate hydrochloride 生成 1,4,5,8,10,10,11,12-Octamethyl-tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5,11-tetraen-9-one
  参考文献：
  名称：

  Synthesis and chemistry of octamethylnaphthalene

  摘要：

  DOI：

  10.1021/jo00799a010
• 作为产物：
  描述：

  6-氨基-2,3-二甲基苯甲酸 在 盐酸 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 以83%的产率得到4,5-dimethylbenzenediazonium-2-carboxylate hydrochloride
  参考文献：
  名称：

  Chance, Jeffrey M.; Geiger, James H.; Okamoto, Yoshio, Journal of the American Chemical Society, 1990, vol. 112, # 9, p. 3540 - 3547

  摘要：

  DOI：

文献信息

• Molecular Turnstiles Regulated by Metal Ions
  作者：Guangxia Wang、Hongmei Xiao、Jiaojiao He、Junfeng Xiang、Ying Wang、Xuebo Chen、Yanke Che、Hua Jiang

  DOI：10.1021/acs.joc.6b00463

  日期：2016.4.15

  A family of novel molecular turnstiles 1–3 composed of two stators with pyridyl binding sites and a different-sized triptycene rotor was synthesized. The molecular turnstiles behave in an open state at room temperature in the absence of metal ions but display significantly different closed states in the presence of Ag+ and Pd2+. The Ag+-mediated turnstiles 1–3Ag exhibited closed states but unreadable

  新的分子入闸的家族1 - 3的两个定子与吡啶结合位点和不同的尺寸的三蝶烯转子组成的合成。分子旋转栅在室温下在没有金属离子的情况下表现为开放状态，而在存在Ag +和Pd 2+的情况下表现出明显不同的封闭状态。Ag +介导的旋转栅1 – 3Ag表现为封闭态，但在室温下的双稳态性却无法读取，因为Ag +介导的大环骨架不能限制转子的旋转；而温度降低，大环框架变得不足以阻止转子的旋转稳定，最终导致可读闭合状态为1 - 3AG。相比之下，Pd 2+介导的大环骨架是稳定的，因此在很宽的温度范围内都可以检测到旋转栅1 – 3Pd的闭合状态。这些发现也得到了DFT计算的支持。
• Molecular Spur Gears Based on a Switchable Quinquepyridine Foldamer Acting as a Stator
  作者：Fu Huang、Guangxia Wang、Lishuang Ma、Ying Wang、Xuebo Chen、Yanke Che、Hua Jiang

  DOI：10.1021/acs.joc.7b01864

  日期：2017.12.1

  quinquepyridine (QPY) foldamer at the second and fourth pyridine rings, respectively, to form molecular spur gears. The studies revealed that a QPY foldamer as a stator can reversibly control the intermeshed and demeshed states of molecular spur gears due to the linear-to-helical conformational switching triggered by complexation/decomplexation.

  两个三茂铁旋转器已分别在第二和第四吡啶环上共价连接到喹吡啶（QPY）折叠架的主链上，以形成分子正齿轮。研究表明，QPY折叠器作为定子可以逆转地控制分子正齿轮的相互啮合和脱离啮合状态，这是由于络合/分解作用引起的线性-螺旋构象转换所致。
• 2,6-Pyridodicarboxamide-Bridged Triptycene Molecular Transmission Devices: Converting Rotation to Rocking Vibration
  作者：Guangxia Wang、Lishuang Ma、Junfeng Xiang、Ying Wang、Xuebo Chen、Yanke Che、Hua Jiang

  DOI：10.1021/acs.joc.5b01778

  日期：2015.11.20

  A series of N-2,N-6-bis(triptycene-9-yl),pyridine-2,6-dicarboxamides 1-4 were designed and synthesized. Due to rotational constraint of the 2,6-diamidopyridine bridge, the triptycene components in the systems are held together. X-ray structures of 1-4 show that the molecules adopt a gear-like geometry in the solid states. DFT (B3LYP/6-31G(d)) calculations predict the gear-like C-2 conformation as global minimum structures for 1 and 2 and suggest that, through a Slippage transition process, rotation of one triptycne component would give rise to a rocking, vibration of the counter component due to the, barrier kit rotation of the triptycene components. VT NMR. studies on 174 show that the pair of triptycene components undergo ceaseless slippage at room temperature but nearly freeze at temperatures as low as 188, K. Decreasing the temperature freezes the slippage between triptycene components as well, thus producing the appearance of phase isomers of 3 and 4. The dynamic features of the studied molecules Indicate that this kind of molecule is able to function as a kind of molecular transmission device for transforming the mode of motion from rotation to rocking vibration.