4-[(5-bromopentyl)oxy]benzonitrile | 91945-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[(5-bromopentyl)oxy]benzonitrile
• 英文别名: 4-(5-bromopentoxy)benzonitrile
• CAS: 91945-01-6
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: ZFADTSGBJUMSPD-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  386.9±22.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(5-bromopentyl)oxy]benzonitrile 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以63%的产率得到p-amidophenoxypentylbromide
  参考文献：
  名称：

  Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine−Aplysinopsin Hybrid Molecule

  摘要：

  In an attempt to synthesize pent amidine - aplysinopsin hybrid molecule 25, a lead molecule 8 (containing Z-configured aplysinopsin moiety) was identified for antileishmanial activity. Optimization of lead 8 provided 24 (containing E-configured aplysinopsin) possessing 10 times more activity and 401-fold less toxicity than the drug pentamidine in cell based assays. Synthesis of 24 was possible, surprisingly, because of two innate reactivities of indole-3-carbaldehyde which provided it in diastereoand regio-selectively pure form without recourse to the long reaction pathway.

  DOI：

  10.1021/jm900564x
• 作为产物：
  描述：

  1,5-二溴戊烷 、 4-羟基苯甲腈 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 4-[(5-bromopentyl)oxy]benzonitrile
  参考文献：
  名称：

  对两种HCMV-VZV抑制剂的发现：长链2-尿嘧啶-3-基-N-（4-苯氧基苯基）乙酰胺的合成，结构活性关系分析和细胞毒性研究

  摘要：

  仍然需要新颖的治疗方法来对抗疱疹病毒感染。本文中，我们报道了一个新的非核苷类抗病毒药物家族的设计，合成和抗病毒评价，该家族衍生自先前报道的人巨细胞病毒（HCMV）抑制剂1- [ω-（4-溴苯氧基）烷基]尿嘧啶衍生物。在N 3处引入N-（4-苯氧基苯基）乙酰胺侧链增加了它们的效力并拓宽了活性谱。该系列中最具活性的化合物在HEL细胞培养物中针对不同的HCMV病毒株和水痘带状疱疹病毒（VZV）复制表现出亚微摩尔活性。对其他DNA和RNA病毒（包括单纯疱疹病毒1/2）的无活性表明了其抗病毒作用的新机制。

  DOI：

  10.1016/j.bmc.2015.09.033

文献信息

• Amidino compounds, their manufacture and methods of treatment
  申请人：Ciba-Geigy Corporation

  公开号：US05451700A1

  公开（公告）日：1995-09-19

  The invention relates to the compounds of the formula ##STR1## wherein the C(.dbd.NH)--NHR.sub.3 group may be in tautomeric or isomeric form, and phamaceutically acceptable salts thereof. The compounds are useful as selective LTB.sub.4 receptor antagonists.

  该发明涉及公式##STR1##中的化合物，其中C(.dbd.NH)--NHR.sub.3基团可以是互变异构体或同分异构体，以及其药用盐。这些化合物可用作选择性LTB.sub.4受体拮抗剂。
• Fast synthesis employing a microwave assisted neat protocol of new monomers potentially useful for the preparation of PDLC films
  作者：M. Teresa Barros、Ana Mouquinho、Krasimira Petrova、Mara Saavedra、João Sotomayor

  DOI：10.2478/s11532-011-0046-2

  日期：2011.8.1

  It has been reported that the length of the molecular chain and the rigidity of molecules influence the structure of the polymer network in PDLC films and hence the electro-optical properties of the composites. Herein, a series of new aromatic monomeric monomethacrylates, bismethacrylates and monovinylbenzene derivatives with a mesogenic core were successfully synthesized under microwave irradiation. The microwave assisted synthesis resulted in decreased reaction times, reduced solvent requirement, increased operational simplicity, and in most cases, improved yields and selectivity.

  已翻译成中文，直接给您结果：

  据报道，分子链的长度和分子的刚性影响PDLC薄膜中聚合物网络的结构，从而影响复合材料的电光性能。在此，一系列新的含芳香基单甲基丙烯酸酯、双甲基丙烯酸酯和单乙烯基苯衍生物，具有向列型核心，在微波辐射下成功合成。微波辅助合成导致反应时间缩短，溶剂需求减少，操作简单性增加，并且在大多数情况下，产率和选择性得到改善。

• Substituted amidino compounds, their manufacture and methods of treatment
  申请人：Ciba-Geigy Corporation

  公开号：US05639768A1

  公开（公告）日：1997-06-17

  The invention relates to the compounds of formula (I) wherein the C(.dbd.NH)--NHR.sub.3 group may be in tautomeric or isomeric form, and pharmaceutically acceptable salts thereof, in which: R.sub.1 is amino which is mono- or disubstituted by a substituent selected from an aliphatic hydrocarbon radical, an araliphatic hydrocarbon radical, an aromatic radical, and a cycloaliphatic hydrocarbon radical or is amino which is disubstituted by a divalent aliphatic hydrocarbon radical or a said radical interrupted by oxygen; R.sub.2 is hydroxy which is etherified by an aliphatic alcohol which is substituted by carboxy, by esterified carboxy or by amidated carboxy; R.sub.3 is hydrogen or an acyl radical which is derived from an organic carbonic acid, an organic carboxylic acid, a sulfonic acid, or a carbamic acid; X.sub.1 and X.sub.3, independently of one another, are oxygen (--O--) or sulphur (--S--); and X.sub.2 is a divalent aliphatic hydrocarbon radical which may be interrupted by an aromatic radical. The compounds are useful as selective LTB.sub.4 receptor antagonists in the treatment of conditions or syndromes in mammals which are responsive to LTB.sub.4 receptor antagonism.

  该发明涉及具有以下式（I）的化合物，其中C(.dbd.NH)--NHR.sub.3基团可以是互变异构体或同分异构体形式，并且其药学上可接受的盐，其中：R.sub.1是氨基，可以是由来自脂肪烃基、芳基烃基、芳基或环脂烃基的取代基单取代或双取代的氨基，也可以是由双价脂肪烃基或被氧中断的所述基团取代的氨基；R.sub.2是被脂肪醇醚化的羟基，该脂肪醇被羧基、酯化羧基或酰胺化羧基取代；R.sub.3是氢或由有机碳酸、有机羧酸、磺酸或碳酸衍生的酰基基团；X.sub.1和X.sub.3，彼此独立地，是氧（--O--）或硫（--S--）；而X.sub.2是可以由芳基中断的双价脂肪烃基。这些化合物在治疗对LTB.sub.4受体拮抗剂敏感的哺乳动物的病症或综合症中作为选择性LTB.sub.4受体拮抗剂是有用的。
• Synthesis of Potent Non-imidazole Histamine H3-Receptor Antagonists
  作者：C. Robin Ganellin、Fabien Leurquin、Antonia Piripitsi、Jean-Michel Arrang、Monique Garbarg、Xavier Ligneau、Walter Schunack、Jean-Charles Schwartz

  DOI：10.1002/(sici)1521-4184(199812)331:12<395::aid-ardp395>3.0.co;2-7

  日期：1998.12

  Histamine has been converted into a non‐imidazole H3‐receptor histamine antagonist by addition of a 4‐phenylbutyl group at the Nα‐position followed by removal of the imidazole ring. The resulting compound, N‐ethyl‐N‐(4‐phenylbutyl)amine, remarkably has a Ki = 1.3 μM as an H3 antagonist. Using this as a lead compound, a novel series of homologous O and S isosteric tertiary amines was synthesised and

  通过在 Nα-位添加 4-苯基丁基，然后去除咪唑环，组胺已转化为非-咪唑 H3-受体组胺拮抗剂。所得化合物 N-乙基-N-（4-苯基丁基）胺作为 H3 拮抗剂具有显着的 Ki = 1.3 μM。使用它作为先导化合物，合成了一系列新的同源 O 和 S 等排叔胺，结构-活性研究提供了 N-（5-苯氧基戊基）吡咯烷（Ki = 0.18 ± 0.10 μM，用于 [3H] 组胺从大鼠中释放大脑皮层突触体），更重要的是，它在体内是活跃的。将 NO2 取代到苯氧基的对位得到 N-(5-p-硝基苯氧基戊基)吡咯烷，UCL 1972 (Ki = 39 ± 11 nM)，ED50 = 1.1 ± 0.6 mg / kg per os in 脑远程小鼠甲基组胺水平。
• Liquid crystalline dihydroazulene photoswitches
  作者：Anne Ugleholdt Petersen、Martyn Jevric、Richard J. Mandle、Edward J. Davis、Stephen J. Cowling、John W. Goodby、Mogens Brøndsted Nielsen

  DOI：10.1039/c5ra18649h

  日期：——

  A large selection of photochromic dihydroazulene (DHA) molecules incorporating various substituents at position 2 of the DHA core was prepared and investigated for their ability to form liquid crystalline phases. Incorporation of an octyloxy-substituted biphenyl substituent resulted in nematic phase behavior and it was possible to convert one such compound partly into its vinylheptafulvene (VHF) isomer

  制备了大量在DHA核的2位掺入各种取代基的光致变色二氢氮杂（DHA）分子，并研究了它们形成液晶相的能力。辛氧基取代的联苯取代基的引入导致向列相行为，并且当在液晶相中被光照射时，可以将一种这样的化合物部分地转化为其乙烯基庚二烯（VHF）异构体。该转化导致相的分子排列增加。随着时间的流逝，亚稳定的VHF返回到DHA，并在此处保持对齐。系统的结构变化表明，DHA和烷基链之间需要一个联芳基间隔基，以实现液晶性，并且该间隔基中的一个芳环不能被三唑取代。