2,3-双(3-甲酰基-2-甲基苯基)萘 | 105077-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,3-双(3-甲酰基-2-甲基苯基)萘
• 英文名称: 2,3-bis(3-formyl-2-methylphenyl)naphthalene
• 英文别名: 3-[3-(3-formyl-2-methylphenyl)naphthalen-2-yl]-2-methylbenzaldehyde
• CAS: 105077-11-0
• 化学式: C₂₆H₂₀O₂
• 分子量: 364.444
• InChiKey: QASLOLGIXFABCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-双(3-甲酰基-2-甲基苯基)萘 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以98%的产率得到2,3-bis(3-(hydroxymethyl)-2-methylphenyl)naphthalene
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008
• 作为产物：
  描述：

  2,3-bis(3-cyano-2-methylphenyl)naphthalene 在 二异丁基氢化铝 作用下， 以 正己烷 、 苯 为溶剂， 反应 24.0h， 以90%的产率得到2,3-双(3-甲酰基-2-甲基苯基)萘
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008

文献信息

• A new synthesis of bridge difunctionalised [2,2]metacyclophanes using a low valent titanium coupling procedure. The first synthesis of [O4]-meta-ortho-meta-orthocyclophanes and their possible conversion into biradicaloid dihydropyrenes.
  作者：Reginald H. Mitchell、S.Ananda Weerawarna

  DOI：10.1016/s0040-4039(00)85503-3

  日期：1986.1

  yields of the bridge difunctionalised [2,2]metacyclophanes 12a,b . Oxidation of these 1,2-diols to the 1,2-diketones was achieved with oxalyl chloride-DMSO followed by iPr2EtN at −30°C, which then on condensation with o-phenylene diamine provided a route to the first zero bridged meta-ortho-meta orthocyclophanes 15a,b . Irradiation of the latter gave purple compounds which we believe are the biradlcaloid

  三苯基二醛11a，b的钛（O）偶联使桥双官能化的[2,2]甲基环环十二烷12a，b的产率为75-85％。用草酰氯-DMSO，然后在-30°C下将iPr 2 EtN氧化，将这些1,2-二醇氧化为1,2-二酮，然后与邻苯二胺缩合，提供了通往第一个零桥的途径亚正交元正环粉15a，b。后者的辐照产生紫色化合物，我们认为是双环类二氢吡啶16a，b。
• Synthesis and Photochromic Properties of Molecules Containing [<i>e</i>]-Annelated Dihydropyrenes. Two and Three Way π-Switches Based on the Dimethyldihydropyrene−Metacyclophanediene Valence Isomerization
  作者：Reginald H. Mitchell、Timothy R. Ward、Yongsheng Chen、Yunxia Wang、S. Ananda Weerawarna、Peter W. Dibble、Michael J. Marsella、Adah Almutairi、Zhi-Qiang Wang

  DOI：10.1021/ja0288136

  日期：2003.3.1

  more than one photochromic switch present and thus have more than a simple "on-off" state. Thermodynamic data are obtained for the thermal closing reactions. The anthrodihydropyrene (12) has the fastest thermal closing (tau(1/2) = 20 min), while the furanodihydropyrene (19') has the slowest (tau(1/2) = 63 h) at 46 degrees C. An electrochemical readout of the state of the switch is demonstrated for the

  描述了几种新的简单负片、一个简单正片和多个负片光致变色材料的合成，这些光色素包含二氢芘-环芳二烯光致变色系统。母体 2,7-di-的 [e]-退火苯并 (7)、萘并 (9)、蒽 (11)、呋喃 (19) 和三苯并 (15) 衍生物的光开孔叔丁基-反式 10b,10c-二甲基-二氢芘 (5) 及其 4,5-二溴衍生物 (13) 被描述为提供相应的环芳二烯，以及它们的光封闭和热封闭二氢芘。将这些与正性光致变色二苯并[e，l]二氢芘（21）和双（二氢芘）芘（44）和（二氢芘苯并）（苯并）间环芘（47）光致变色的结果进行比较，它们具有多个光致变色开关，因此不仅仅是简单的“开-关”状态。获得热闭合反应的热力学数据。蒽二氢芘 (12) 的热闭合速度最快 (tau(1/2) = 20 分钟)，而呋喃二氢芘 (19') 的热闭合最慢 (tau(1/2) = 63 h) 在 46 摄氏度。对苯并二氢芘 (7)
• MITCHELL, R. H.;WEERAWARNA, S. A., TETRAHEDRON LETT., 1986, 27, N 4, 453-456
  作者：MITCHELL, R. H.、WEERAWARNA, S. A.

  DOI：——

  日期：——