4-methoxy-1-tetradecylbenzene | 22165-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-1-tetradecylbenzene
• 英文别名: 4-Methoxy-1-tetradecyl-benzene；1-methoxy-4-tetradecylbenzene
• CAS: 22165-05-5
• 化学式: C₂₁H₃₆O
• 分子量: 304.516
• InChiKey: YTDIXKXNHNGXQI-UHFFFAOYSA-N

物化性质

• 沸点：
  210 °C(Press: 60 Torr)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methoxy-1-tetradecylbenzene 在 吡啶 、 盐酸 、 silicic acid-boric acid 、 三溴化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 Petroleum ether 为溶剂， 反应 128.0h， 生成 1-hydroxy-3-(3-tetradecylphenoxy)propan-2-yl acetate
  参考文献：
  名称：

  Analogs of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain

  摘要：

  Analogues of platelet activating factor (PAF) in which the ether oxygen has been removed (6) and in which the alkoxy chain at C1 has been replaced with a o-, p-, or m-alkylphenoxy group (30, 31, and 35, respectively) have been prepared. Compound 6 shows reduced platelet aggregation and hypotensive activity in comparison with C16 and C18 PAF. The results obtained for compounds 30, 31, and 35 indicate that the hypotensive and platelet aggregating responses are sensitive to structural modification of the ether chain. The ortho analogue 30 shows no platelet aggregating activity and only a weak hypotensive response. The para analogue 31 exhibits a moderate decrease in activity in both assays. The meta analogue 35 is the most active of the three.

  DOI：

  10.1021/jm00375a016
• 作为产物：
  描述：

  1-(4-methoxy-phenyl)-tetradecan-1-one 在 氢氧化钾 、 一水合肼 、 二乙二醇 作用下， 生成 4-methoxy-1-tetradecylbenzene
  参考文献：
  名称：

  Matsuda et al., Technology Reports of the Osaka University, 1956, vol. 6, p. 393

  摘要：

  DOI：

文献信息

• Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
  作者：Yadong Gao、Chao Yang、Songlin Bai、Xiaolei Liu、Qingcui Wu、Jing Wang、Chao Jiang、Xiangbing Qi

  DOI：10.1016/j.chempr.2019.12.010

  日期：2020.3

  Transition-metal-catalyzed cross-coupling reactions between naturally abundant sp3-hybridized carbon centers facilitate access to diverse molecules with complex three-dimensional structures. Organometallic compounds are among one of the most powerful reagents that are broadly used in carbon–carbon bond formations. Although sp2-hybridized organometallic compounds are widely employed in cross-couplings, sp3-hybridized

  自然丰富的sp 3-杂化碳中心之间的过渡金属催化交叉偶联反应有助于获得具有复杂三维结构的各种分子。有机金属化合物是最强大的试剂之一，广泛用于碳-碳键的形成。尽管sp 2-杂化的有机金属化合物广泛用于交叉偶联，但是sp 3-杂化的有机金属偶联剂的开发较少。在这里，我们报告可见光诱导的单个镍催化的C（sp 3）–C（sp 3），C（sp 3）–C（sp 2）和C（sp 3）–C（sp）使用烷基锆茂的交叉偶联反应，该反应很容易从末端或内部未活化的烯烃通过加氢锆和链步反应就地生成。该方法温和，适用于多种底物，包括伯，仲，叔烷基，芳基，烯基，炔基卤化物和各种烯烃。机理研究表明，镍催化的自由基交叉偶联是一种新颖的途径，代表了锆锆茂的首次可见光诱导的转变。
• Nickel‐Catalyzed C( <i>sp</i> ² )−C( <i>sp</i> ³ ) Kumada Cross‐Coupling of Aryl Tosylates with Alkyl Grignard Reagents
  作者：Aleksandra Piontek、Wioletta Ochędzan‐Siodłak、Elwira Bisz、Michal Szostak

  DOI：10.1002/adsc.201801586

  日期：2019.5.14

  Aryl tosylates are an attractive class of electrophiles for cross‐coupling reactions due to ease of synthesis, low price, and the employment of C−O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni‐catalyzed C(sp2)−C(sp3) Kumada cross‐coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross‐coupling

  由于易于合成，价格低廉和使用C-O亲电试剂，芳基甲苯磺酸盐是用于交叉偶联反应的一类亲电试剂，但是，芳基甲苯磺酸盐的反应性很低。在此，我们报告了Ni催化的C（sp 2）-C（sp 3）Kumada将芳基甲苯磺酸盐与伯烷基和仲烷基格氏试剂进行交叉偶联。该方法通过与具有β-氢的具有挑战性的烷基有机金属交叉偶联，从而提供有价值的烷基芳烃，这些金属容易发生β-氢化物消除和均相偶联。该反应由空气和湿气稳定的Ni（II）预催化剂催化。各种各样的电子可变的芳基甲苯磺酸盐，包括双甲苯磺酸盐，都经历了这种转变，许多例子都适合在温和的室温条件下使用。Ar-X交叉偶联与简便的Ar-OH活化/交叉偶联策略相结合，可以与具有挑战性的烷基有机金属进行正交交叉偶联。此外，我们证明了该方法可在TON达到2000的情况下运行，
• Controlling the formation of heliconical smectic phases by molecular design of achiral bent-core molecules
  作者：Marco Poppe、Mohamed Alaasar、Anne Lehmann、Silvio Poppe、Maria-Gabriela Tamba、Marharyta Kurachkina、Alexey Eremin、Mamatha Nagaraj、Jagdish K. Vij、Xiaoqian Cai、Feng Liu、Carsten Tschierske

  DOI：10.1039/c9tc06456g

  日期：——

  Fluids with spontaneous helical structures formed by achiral low molecular mass molecules is a newly emerging field with great application potential. Here, we explore the chemical mechanisms of the helix formation by systematically modifying the structure of a bent 4-cyanoresorcinol unit functionalized with two different phenyl benzoate based aromatic rods and terminated with two alkyl chains of variable

  由非手性低分子量分子形成的具有自发螺旋结构的流体是一个新兴的领域，具有巨大的应用潜力。在这里，我们通过系统地修饰弯曲的4-氰基间苯二酚单元的结构，探索了螺旋形成的化学机理，该4-氰基间苯二酚单元被两个基于苯甲酸苯酯的不同芳族棒官能化并被两个可变长度的烷基链终止。这些非手性化合物中的大多数会自组装，从而在较宽的温度范围内形成短间距螺旋液晶相。在某些情况下，它在没有任何竞争性低温相的情况下发生。我们证明，如果近晶层中分子的倾斜角约为18–20°，并且该过渡与层间倾斜相关性的变化相一致，则镜像对称的破坏中间相会发生在顺电（反）铁电转变处。在这种转变的附近，产生了场感应的螺旋相以及具有极化随机结构的新螺旋相。这些研究为未来设计的非手性分子提供了一个蓝图，这些分子能够通过螺旋液晶相的形成而自发地镜像对称性破坏。
• 4-Methylresorcinol based bent-core liquid crystals with azobenzene wings – a new class of compounds with dark conglomerate phases
  作者：Mohamed Alaasar、Marko Prehm、Marcel Brautzsch、Carsten Tschierske

  DOI：10.1039/c4tc00533c

  日期：——

  Stochastic achiral symmetry breaking in soft matter systems, leading to conglomerates of macroscopically chiral domains (so-called dark conglomerate = DC phases) is of contemporary interest from a fundamental scientific point of view as well as for numerous potential applications in chirality sensing and non-centrosymmetric materials. Herein we report the synthesis and investigation of first azobenzene containing bent-core mesogens derived from 4-methylresorcinol forming DC phases with a new structure, distinct from the known fluid sponge-like distorted smectic phases as well as from the helical nano-filament phases (HNF phases, B4 phases). The effects of chain length and other structural modifications on achiral symmetry breaking were investigated. Homologues with relatively short alkyl chains form achiral intercalated lamellar LC phases (B6 phases), but on increasing the chains, these are replaced by the chiral and optically isotropic DC phases. Compounds with the longest alkyl chains form low birefringent crystalline conglomerates which represent less distorted versions of the optically isotropic DC-phases. Introducing additional peripheral substituents at both outer rings removes the DC phases. The DC phases were also removed and replaced by modulated smectic phases if the azo groups were replaced by ester units, showing that azo groups favour DC phase formation with new nanostructures, distinct from the previously known types.

  软物质体系中的随机非手性对称破缺会导致宏观手性域的集合体（即所谓的暗集合体 = DC 相），从基础科学的角度以及手性传感和非中心对称材料中的众多潜在应用来看，这种破缺具有时代意义。在此，我们报告了第一种由 4-甲基间苯二酚衍生的含弯核中间体偶氮苯的合成与研究，这些中间体形成了具有新结构的 DC 相，有别于已知的流体海绵状扭曲构造相以及螺旋状纳米纤维相（HNF 相，B4 相）。我们研究了链长和其他结构修饰对非手性对称性破坏的影响。烷基链相对较短的同系物形成了非手性夹层片状低浓相（B6 相），但随着烷基链的增加，这些同系物被手性和光学各向同性的 DC 相所取代。烷基链最长的化合物会形成低双折射结晶团块，代表光学各向同性 DC 相的较小变形版本。在两个外环上引入额外的外围取代基可以消除直流相。如果将偶氮基团替换为酯单元，则直流相也会消失，取而代之的是调制的平滑相，这表明偶氮基团有利于形成具有新纳米结构的直流相，不同于之前已知的类型。
• Phosphocholine derivatives having antihypertensive action
  申请人：American Cyanamid Company

  公开号：US04640913A1

  公开（公告）日：1987-02-03

  Phosphocholine derivatives and compositions are described which are useful as hypotensive agents and in the treatment of hypertension in warm-blooded animals.

  本文描述了磷酸胆碱衍生物和组合物，其可用作降压剂和治疗恒温动物的高血压。