3,6-dioctylphthalonitrile | 128912-48-1

• 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: 3,6-dioctylphthalonitrile
• 英文别名: 3,6-Dioctylbenzene-1,2-dicarbonitrile
• CAS: 128912-48-1
• 化学式: C₂₄H₃₆N₂
• 分子量: 352.563
• InChiKey: CBCCKPOQISXJJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-dioctylphthalonitrile 在 甲基锂 、 溶剂黄146 作用下， 以 乙醚 、 环己醇 为溶剂， 反应 4.17h， 以35%的产率得到1,4,8,11,15,18,22,25-octaoctylphthalocyanine
  参考文献：
  名称：

  改进非外围烷基取代的四苯并三氮杂卟啉的合成

  摘要：

  摘要 对非外围烷基取代的大环分子 1,4,8,11,15,18,22,25-八烷基四苯并三氮杂卟啉 (CnTBTAPH2) 合成的改进进行了研究。在3,6-二烷基邻苯二甲腈到CnTBTAPH2的反应中，通过用甲基锂代替常规格氏试剂，产率得到显着提高。使用稳定溶剂的改进程序对于反应系统的放大以及产率的提高非常有效。

  DOI：

  10.1080/15421406.2017.1348802
• 作为产物：
  描述：

  (2R,3R)-1,4-dioctyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile 生成 3,6-dioctylphthalonitrile
  参考文献：
  名称：

  MCKEOWN, NEIL B.;CHAMBRIER, ISABELLE;COOK, MICHAEL J., J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1169-1177

  摘要：

  DOI：

文献信息

• Synthesis and characterisation of some mesogenic mononuclear and multinuclear phthalocyanines
  作者：Geoffrey C. Bryant、Michael J. Cook、Timothy G. Ryan、Andrew J. Thorne

  DOI：10.1016/0040-4020(95)00927-2

  日期：1996.1

  tri-nuclear phthalocyanines, ie derivatives containing two or three phthalocyanine rings. These compounds have been characterised by elemental analysis and low resolution field desorption mass spectrometry, FD-MS. 1H NMR spectroscopy and gel permeation chromatography of selected examples provide supporting data. Visible region spectroscopy of dilute solutions of the multinuclear phthalocyanines in cyclohexane

  已经合成了带有一个或两个羟烷基链的八取代的酞菁，并且其液晶行为通过偏光显微镜和差示扫描量热法表征。这些化合物形成具有六边形或矩形对称的盘状柱状中间相。实例已经用作合成介晶二核和三核酞菁的前体，即包含两个或三个酞菁环的衍生物。这些化合物已通过元素分析和低分辨率场解析质谱FD-MS进行了表征。1个所选实施例的1 H NMR光谱学和凝胶渗透色谱法提供了支持数据。环己烷中多核酞菁的稀溶液的可见区光谱（低至5×10 -7 mol dm -3的浓度，预期分子间聚集最小）表明该化合物作为“封闭”构象异构体之间的平衡存在其中两个环cofacially布置（宽带中心在约645nm）和具有类似于简单的前体的酞菁的吸收带的开放形式，λ最大约 730纳米 封闭的构象异构体在极性更高的介质（例如10％甲苯-90％乙醇）中更受欢迎。实例已经以均匀厚度的旋涂膜沉积在载玻片上。
• Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles
  作者：Daniel J Tate、Rémi Anémian、Richard J Bushby、Suwat Nanan、Stuart L Warriner、and Benjamin J Whitaker

  DOI：10.3762/bjoc.8.14

  日期：——

  It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobility of 0.14 cm²·V⁻¹·s⁻¹ within the temperature range of the columnar hexagonal phase, that is 169–189 °C.

  已经表明，邻苯二腈的碱性引发的环状寡聚反应受到庞大的α-取代基的偏爱，从而可以直接且高产率地获得无金属酞菁。具有八个α-异庚基取代基的酞菁在柱状六角相温度范围内（即169–189°C）具有高达0.14 cm²·V⁻¹·s⁻¹的飞行时间孔迁移率。
• Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain length
  作者：Lydia X. Sosa-Vargas、Isabelle Chambrier、Colin J. MacDonald、Simon J. Coles、Graham J. Tizzard、Andrew N. Cammidge、Michael J. Cook

  DOI：10.1142/s108842461350020x

  日期：2013.6

  The preparation of some peripherally substituted (2,3,9,10,16,17,23,24) and non-peripherally substituted (1,4,8,11,15,18,22,25) octaalkyl lead(II) phthalocyanines with different alkyl chain lengths (6, 7, 8 or 9 carbons) is described and a comparison of some of their properties reported. X-ray structure analyses of the isomeric peripheral and non-peripheral octakis(octyl)phthalocyaninato lead(II) compounds reveal a greater degree of distortion of the ligand ring system from planarity in the former derivative. The series of peripherally substituted octaalkyl lead(II) phthalocyanines exhibit columnar liquid crystal behavior whereas the non-peripherally substituted isomers do not. The lability of the lead ion was investigated using ¹ H NMR spectrometry under a specific set of conditions (8.8 × 10^-4 M solutions of the phthalocyanine in d₈-toluene containing d₄-acetic acid 2.06 × 10^-5 M). All the compounds underwent acid catalyzed demetalation at rates dependent upon the location of the substituents and, more surprisingly, the chain length of the alkyl groups. Under these conditions the lead ion within each of the peripherally substituted octaalkyl lead phthalocyanines was more labile than that in the non-peripherally substituted isomer.

  本文介绍了一些外周取代（2,3,9,10,16,17,23,24）和非外周取代（1,4,8,11,15,18,22,25）、具有不同烷基链长度（6、7、8 或 9 个碳原子）的八烷基酞菁铅（II）的制备方法，并对它们的一些性质进行了比较。对同分异构的外周和非外周辛基酞菁族铅（II）化合物的 X 射线结构分析表明，前者衍生物中配体环系统的平面变形程度更大。外周取代的八烷基酞菁铅（II）系列表现出柱状液晶行为，而非外周取代的异构体则没有。在一组特定条件下（酞菁在含有 2.06 × 10-5 M d4-乙酸的 d8-甲苯中的 8.8 × 10-4 M 溶液），使用 1 H NMR 光谱法研究了铅离子的稳定性。所有化合物都在酸催化下发生了脱金属反应，脱金属的速度取决于取代基的位置，更令人惊讶的是取决于烷基的链长。在这些条件下，外周取代的八烷基酞菁铅中的铅离子比非外周取代的异构体中的铅离子更易变。
• Catalytic epoxidation of stilbenes with non-peripherally alkyl substituted carbonyl ruthenium phthalocyanine complexes
  作者：Charles A. Enow、Charlene Marais、Barend C.B. Bezuidenhoudt

  DOI：10.1142/s1088424612500459

  日期：2012.4

  A number of novel carbonyl(1,4,8,11,15,18,22,25-octaalkylphthalocyaninato)-ruthenium(II) complexes were prepared by metal insertion with Ru₃(CO)₁₂. The new compounds have been characterized by¹H NMR,¹³C NMR, IR, UV-vis and mass spectroscopy. This study demonstrated that this type of complexes and specifically carbonyl(1,4,8,11,15,18,22,25-octahexylphthalo-cyaninato)ruthenium(II) and carbonyl[1,4,8,11,15,18,22,25-octa(2-cyclohexylethyl)phthalocyaninato]-ruthenium(II), exhibit high catalytic activity and stability in the epoxidation of stilbenes with 2,6-dichloropyridine N-oxide as oxidant.

  通过金属插入 Ru3(CO)12 制备了一些新型羰基（1,4,8,11,15,18,22,25-八烷基酞菁）-钌（II）配合物。新化合物通过 1H NMR、13C NMR、IR、UV-vis 和质谱进行了表征。该研究表明，这类配合物，特别是羰基（1,4,8,11,15,18,22,25-八己基邻苯二甲酰）钌（II）和羰基[1,4,8,11,15,18,22、和羰基[1,4,8,11,15,18,22,25-八（2-环己基乙基）酞氰基]-钌（II）在以 2,6-二氯吡啶 N-氧化物为氧化剂的二苯乙烯环氧化反应中表现出较高的催化活性和稳定性。
• Design and synthesis of liquid crystalline phthalocyanines: combinations of substituents that promote the discotic nematic mesophase
  作者：Andrew D. Garland、Isabelle Chambrier、Andrew N. Cammidge、Michael J. Cook

  DOI：10.1016/j.tet.2015.04.006

  日期：2015.9

  exhibit only columnar mesophases, which is common among liquid crystalline phthalocyanines. However, four examples form the rare discotic nematic mesophase. A general structural feature is deduced in that this rare phase is favoured when the number of linking atoms in the hydroxyalkyl chain exceeds twice the number of carbon atoms in any one of the six common alkyl chains, disrupting the columnar packing

  一个同源系列的十四个无金属的1,4,8,11,15,18-六（烷基）-22-甲基-25-羟烷基酞菁衍生物可询问六个烷基链和促进热致向列液晶行为的羟烷基链的长度。除两种化合物外，所有化合物均形成中间相。其余八种化合物仅表现出柱状中间相，这在液晶酞菁中很常见。然而，四个例子形成了罕见的盘状向列中间相。推断出一般的结构特征是，当羟烷基链中的连接原子数超过六个普通烷基链中任何一个的碳原子数的两倍时，这种稀有相是有利的，从而破坏了柱状堆积排列。此外，