3-羟基-4-苯氧基丁腈 | 57281-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-羟基-4-苯氧基丁腈
• 英文名称: 3-hydroxy-4-(phenyloxy)butanenitrile
• 英文别名: 3-hydroxy-4-phenoxybutanenitrile
• CAS: 57281-49-9
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: KJJPPYGFSUFUAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-4-苯氧基丁腈 在 sodium tetrahydroborate 、 三氯化铝 作用下， 生成 3-Hydroxy-4-phenoxy-butylamin
  参考文献：
  名称：

  1-氨基-3-芳氧基-2-丙醇中乙烯醇的质谱损失。24.关于氮化合物质谱行为的交流† ‡

  摘要：

  电子冲击下1-氨基-3-芳氧基-2-丙醇中乙烯醇的损失

  DOI：

  10.1002/hlca.19770600113
• 作为产物：
  描述：

  苯基缩水甘油醚 在 potassium cyanide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以58%的产率得到3-羟基-4-苯氧基丁腈
  参考文献：
  名称：

  Synthesis of 4-Substituted 3,3-Difluoropiperidines

  摘要：

  Synthetic strategies toward 4-substituted 3,3-difluoropiperidines were evaluated. 4-Alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines were synthesized via 1,4-addition of ethyl bromodifluoroacetate to 3-substituted acrylonitriles in the presence of copper powder, followed by borane reduction of the cyano substituent, lactamization, and reduction of the lactam. This method was applied to establish the synthesis of N-protected 3,3-difluoroisonipecotic acid, a fluorinated gamma-amino, acid. 4-Benzyloxy-3,3-difluoropiperidine was prepared using an analogous methodology and was converted to N-protected 3,3-difluoro-4,4-dihydroxypiperidine, a compound with high potential as a building block in medicinal chemistry.

  DOI：

  10.1021/jo902164z

文献信息

• Biocatalytic Cascade for the Synthesis of Enantiopure β-Azidoalcohols and β-Hydroxynitriles
  作者：Joerg H. Schrittwieser、Iván Lavandera、Birgit Seisser、Barbara Mautner、Wolfgang Kroutil

  DOI：10.1002/ejoc.200900091

  日期：2009.5

  one-pot reaction sequence starting from prochiral α-chloroketones leading to enantiopure β-azidoalcohols and β-hydroxynitriles is described. Asymmetric bioreduction of α-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide

  描述了从前手性 α-氯酮开始导致对映纯 β-叠氮醇和 β-羟基腈的三步、两酶、一锅反应序列。通过由醇脱氢酶 (ADH) 催化的氢转移对 α-氯酮进行不对称生物还原，在第一步中建立了立体中心，以提供对映纯的氯醇中间体。随后通过非选择性卤代醇脱卤酶 (Hhe) 催化环氧化物的生物催化闭环和用叠氮化物 N3- 或氰化物 CN- 的亲核开环进行完全保留构型，得到对映体纯的 β-叠氮醇和 β-羟基腈，分别。合成了各种光学纯 β-叠氮醇和 β-羟基腈的两种对映异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• LiOH-Catalyzed Simple Ring Opening of Epoxides Under Solvent-Free Conditions
  作者：Najmedin Azizi、Alireza Khajeh-Amiri、Hossein Ghafuri、Mohammad Bolourtchian

  DOI：10.1080/10426500903127573

  日期：2010.6.30

  sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions.

  已发现 LiOH 是一种非常简单且选择性的催化剂，可通过环氧化物与芳香族、脂肪族和杂环硫醇以及三甲基氰基氰化物在室温下在无溶剂条件下开环快速温和地合成 β-羟基硫化物和 β-羟基腈使适应。所有反应都在短时间内令人满意地进行，并在温和的反应条件下以良好的收率和高区域选择性和化学选择性提供相应的产物。
• Ring Opening of Epoxides with Acetone Cyanohydrin Catalyzed by Lanthanoid(III) Alkoxides
  作者：Hiroshi Ohno、Atsunori Mori、Shohei Inoue

  DOI：10.1246/cl.1993.975

  日期：1993.6

  Ring opening of epoxide and aziridine with acetone cyanohydrin is promoted by a catalytic amount of lanthanoid(III) alkoxide to provide β-hydroxy nitrile and β-amino nitrile, respectively.

  催化量的镧系元素(III)醇盐促进环氧化物和氮丙啶与丙酮氰醇的开环，分别提供β-羟基腈和β-氨基腈。
• Easy direct stereo- and regioselective formation of β-hydroxy nitriles by reaction of 1,2-epoxides with potassium cyanide in the presence of metal salts
  作者：Marco Chini、Paolo Crotti、Lucilla Favero、Franco Macchia

  DOI：10.1016/s0040-4039(00)92305-0

  日期：1991.1

  A simple efficient, anti stereoselective, and highly regioselective method for the synthesis of β-hydroxy nitriles by the direct opening of 1,2-epoxides with KCN in acetonitrile, in the presence of metal salts, is described. This new method appears to be competitive with the other methods previously reported.

  描述了一种简单有效，抗立体选择性和高度区域选择性的方法，该方法通过在金属盐存在下用乙腈中的KCN直接打开1,2-环氧化物来合成β-羟基腈。这种新方法似乎与以前报道的其他方法竞争。
• Micellar media for the efficient ring opening of epoxides with CN–, N3–, NO3–, NO2–, SCN–, Cl– and Br– catalyzed with Ce(OTf)4
  作者：Nasser Iranpoor、Habib Firouzabadi、Marzieh Shekarize

  DOI：10.1039/b211697a

  日期：2003.2.11

  Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN−, N3−, NO3−, NO2−, SCN−, Br− and Cl−, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN− is an easy procedure for the high yielding preparation of epoxy sulfides.

  引入胶束介质以高效地打开环氧化物，使用如CN⁻、N3⁻、NO3⁻、NO2⁻、SCN⁻、Br⁻和Cl⁻等亲核盐，并用Ce(OTf)₄催化。这种方法是在温和反应条件下合成不同β-取代醇的高效程序。与SCN⁻的反应是一种简单的程序，用于高产率制备环氧硫化物。