4-叔丁氧基苯甲腈 | 185259-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-叔丁氧基苯甲腈
• 中文别名: 4-叔-丁氧基苯甲腈
• 英文名称: 4-(tert-butoxy)benzonitrile
• 英文别名: tert-butyl 4-cyanophenyl ether；4-Tert-butoxybenzonitrile；4-[(2-methylpropan-2-yl)oxy]benzonitrile
• CAS: 185259-36-3
• 化学式: C₁₁H₁₃NO
• mdl: MFCD03425273
• 分子量: 175.23
• InChiKey: WLWYCCYGVDZFMS-UHFFFAOYSA-N

物化性质

• 沸点：
  95°C 0,8mm
• 密度：
  1.01±0.1 g/cm3(Predicted)
• 闪点：
  95°C/0.8mm
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 安全说明：
  S28,S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3276
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P312,P321,P322,P330,P332+P313,P337+P313,P362,P363,P501
• 危险性描述：
  H302,H312,H315,H319,H332
• 储存条件：
  保存方法：应存放在密闭、阴凉、通风良好的干燥处。

反应信息

• 作为反应物：
  描述：

  4-叔丁氧基苯甲腈 在 lithium aluminium tetrahydride 、 TEA 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (4-tert-Butoxy-benzylamino)-acetic acid ethyl ester
  参考文献：
  名称：

  Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P

  摘要：

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2
• 作为产物：
  描述：

  对氟苯腈 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以95%的产率得到4-叔丁氧基苯甲腈
  参考文献：
  名称：

  通过无过渡金属，苄基胺和腈的碱介导的脱氨基偶合反应合成咪唑

  摘要：

  本文报道了用于制备取代的咪唑的无过渡金属的直接合成方法。碱促进的苄胺与腈的脱氨性偶联导致一步合成2,4,5-三取代的咪唑并释放出氨。该方案为从容易获得的起始原料合成有价值的咪唑衍生物提供了实用的策略。

  DOI：

  10.1039/c7cc08322j

文献信息

• From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions
  作者：Dong-Yu Wang、Ze-Kun Yang、Chao Wang、Ao Zhang、Masanobu Uchiyama

  DOI：10.1002/anie.201712618

  日期：2018.3.26

  We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope

  我们通过醇/酚（ROH）与芳基铵盐（ArNMe反应开发了用于芳基醚的合成的简单且直接的方法3 +），它很容易从苯胺制备（ArNR' 2，R'= H或Me） 。该反应在室温下顺利地且快速地进行（在几个小时内）在市售的碱，例如KO的存在吨卜或KHMDS，并具有相对于二者ROH和ArNR'宽的底物范围2。它具有可扩展性，并且与各种功能组兼容。
• MODULATORS OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE
  申请人：Durand-Reville Thomas

  公开号：US20110021513A1

  公开（公告）日：2011-01-27

  The present invention relates to modulators of IRAK kinase and provides compositions comprising such modulators, as well as methods therewith for treating conditions or diseases mediated by or associated with IRAK kinase.

  本发明涉及IRAK激酶的调节剂，并提供包含这些调节剂的组合物，以及利用这些调节剂治疗由IRAK激酶介导或相关的疾病或病症的方法。
• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Photochemistry of Aryl <i>tert</i>-Butyl Ethers in Methanol:  The Effect of Substituents on an Excited State Cleavage Reaction
  作者：D. P. DeCosta、A. Bennett、A. L. Pincock、J. A. Pincock、R. Stefanova

  DOI：10.1021/jo0002893

  日期：2000.6.1

  from photo-Fries reaction. The corresponding 4-cyanophenyl 1-adamantyl ether, 9, also gave 1-methoxyadamantane 16 (16%), indicating that, at least for this ether, some of the products were ion-derived. Quenching studies with 2,3-dimethylbutadiene for the tert-butyl ethers indicated that these reactions were occurring from the singlet excited state. Rate constants for the reaction, obtained from quantum

  一组10个取代的芳基叔丁基醚8a-j在甲醇中的光解得到主要产物，相应的苯酚以及由光-弗里斯反应产生的叔丁基取代的苯酚。相应的4-氰基苯基1-金刚烷基醚9，也得到了1-甲氧基金刚烷16（16％），表明至少对于该醚而言，一些产物是离子衍生的。用2，3-二甲基丁二烯对叔丁基醚进行猝灭研究表明，这些反应是从单重态激发态发生的。从量子产率和单重态寿命获得的反应速率常数与sigma（h）（）（nu）值合理相关，rho = -0.77（r = 0.975），这对于反应是出乎意料的其中在过渡态中断裂的键的极性预期为-O（delta-）。
• Convenient two-step synthesis of highly functionalized benzo-fused 1,4-diazepin-3-ones and 1,5-diazocin-4-ones by sequential Ugi and intramolecular S N Ar reactions
  作者：Simon Vézina-Dawod、Nicolas Gerber、Xinxia Liang、Eric Biron

  DOI：10.1016/j.tet.2017.09.028

  日期：2017.11

  pharmacological properties and peptidomimetic abilities. We report herein a rapid and efficient two-step synthesis of polysubstituted 1,4-benzodiazepin-3-ones and 1,5-benzodiazocin-4-ones using a multicomponent condensation/cyclization strategy. The approach uses an Ugi four-component reaction to condense readily available Nα-Fmoc-amino acids, amines and isocyanides with a 2-fluorobenzaldehyde derivative

  苯并二氮杂pin酮是重要的杂环族，具有非常诱人的药理特性和拟肽能力。我们在此报告了一种使用多组分缩合/环化策略快速有效地两步合成多取代的1,4-苯并二氮杂-3-酮和1,5-苯并二氮杂-4-酮的方法。该方法使用的Ugi四组分反应以冷凝容易获得Ñ α-带有2-氟苯甲醛衍生物的-Fmoc-氨基酸，胺和异氰酸酯，然后一锅去除Fmoc-基团，分子内芳族亲核取代基用于闭环和侧链脱保护。所描述的方法可接近带有多种官能化取代基的苯并稠合的7和8元环，并用于有效制备三和四取代的1,4-苯并二氮杂-3-酮和1,5-苯并重氮-4 -通过两个简单的步骤即可获得高产量。