3-Dicyanmethylen-1,5-dimethyl-cyclohexen | 104217-15-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-Dicyanmethylen-1,5-dimethyl-cyclohexen
• 英文别名: 2-(3,5-dimethylcyclohex-2-enylidene)malononitrile；(3,5-dimethyl-cyclohex-2-enylidene)-malononitrile；(3,5-Dimethyl-cyclohex-2-enyliden)-malononitril；2-(3,5-Dimethylcyclohex-2-en-1-ylidene)propanedinitrile
• CAS: 104217-15-4
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: URWZJAHQKMBLFI-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  170-175 °C(Press: 18 Torr)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-Dicyanmethylen-1,5-dimethyl-cyclohexen 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 三乙胺 作用下， 生成 [5-methyl-3-(3-methyl-3H-benzoxazol-2-ylidenemethyl)-cyclohex-2-enylidene]-malononitrile
  参考文献：
  名称：

  Photographic sensitizing dyes and emulsions containing them

  摘要：

  公开号：

  US02882158A1
• 作为产物：
  描述：

  3,5-二甲基-2-环己烯-1-酮 、 丙二腈 生成 3-Dicyanmethylen-1,5-dimethyl-cyclohexen
  参考文献：
  名称：

  Photographic sensitizing dyes and emulsions containing them

  摘要：

  公开号：

  US02882158A1

文献信息

• The influence of pyrrole linked to the π-conjugated polyene on crystal characteristics and polymorphism
  作者：Pil-Joo Kim、O.-Pil Kwon、Mojca Jazbinsek、Hoseop Yun、Peter Günter

  DOI：10.1016/j.dyepig.2009.12.011

  日期：2010.7

  Novel pyrrole-based polyene derivatives bearing various different substituents were synthesized to investigate the influence of molecular conformational change (rotational isomerization) of a π-conjugated bridge on crystal characteristics and polymorphism. The pyrrole-based polyene crystals exhibited strong second harmonic generation efficiency that was ∼two orders of magnitude larger than that of

  合成了带有各种不同取代基的新型基于吡咯的多烯衍生物，以研究π共轭桥的分子构象变化（旋转异构化）对晶体特性和多态性的影响。吡咯基多烯晶体表现出很强的二次谐波产生效率，比尿素的产生效率高约两个数量级。带有不对称吡咯的发色团容易形成多晶型物，而具有对称二甲基氨基苯基基团的晶体仅显示一种晶体结构。在吡咯基发色团中观察到的多态性归因于旋转异构化的存在，其中次要旋转异构体在晶体形成过程中表现出“自加效应”。
• Phenolic Polyene Crystals with Tailored Physical Properties and Very Large Nonlinear Optical Response
  作者：O-Pil Kwon、Seong-Ji Kwon、Mojca Jazbinsek、Ji-Youn Seo、Jong-Taek Kim、Jung-In Seo、Yoon Sup Lee、Hoseop Yun、Peter Günter

  DOI：10.1021/cm103426w

  日期：2011.1.25

  We report on the design of the nonlinear optical organic phenolic polyene crystals for tailoring their physical properties to achieve optimized crystals for applications. New phenolic OH2 (2-(3-(4-hydroxystyryl)-5-methylcyclohex-2-enylidene)malononitrile) molecules keep the main supramolecular interaction sites and the high hyperpolarizability of the previously studied state-of-the-art OH1 (2-(3-(4-hydroxystyryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile) and OH3 (2-(3-(4-hydroxystyryl)cyclohex-2-enylidene)malononitrile) molecules but contain different substituents in the non-pi-conjugated part of the molecule, which affects the crystal packing and the physical properties. The acentric OH2 crystals exhibit an improved molecular ordering compared to OH1 crystals, leading to a high order parameter cos(3) theta(p) = 0.92, which is close to optimal for electro-optics and terahertz generation applications. They also exhibit a considerably improved solution growth characteristics compared to the isomorphous OH3 crystals, based on the increase of the solubility by a factor of 2. The acentric OH2 crystals exhibit a large macroscopic nonlinearity with up to twice the second harmonic generation efficiency of OH1 and OH3 crystals as well as the possibility to grow bulk crystals suitable for optical investigations. Furthermore, we evaluate theoretically that the head-to-tail intermolecular hydrogen bonds occurring in phenolic polyene crystals may enhance the hyperpolarizability of the molecules by 50% or more.