γ-Butoxy-β-hydroxy-butyronitril | 18282-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: γ-Butoxy-β-hydroxy-butyronitril
• 英文别名: 4-Butoxy-3-hydroxybutanenitrile
• CAS: 18282-79-6
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: XSLZGIVXKMWZKR-UHFFFAOYSA-N

物化性质

• 沸点：
  302.7±27.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  γ-Butoxy-β-hydroxy-butyronitril 在 sodium hydroxide 作用下， 生成 γ-Butoxy-crotononitril
  参考文献：
  名称：

  环氧氯丙烷衍生物的研究。三、一种制备γ-烷氧基-γ-丁内酯的新方法

  摘要：

  当衍生自环氧氯丙烷和醇的烷基缩水甘油醚用氰化钠处理时，得到相应的γ-烷氧基-β-羟基丁腈(I)。I 用碱金属氢氧化物水溶液水解，然后酸化和蒸馏，得到 γ-烷氧基-γ-丁内酯 (II)。II的结构通过化学和物理手段得到证实。还研究了 I 到 II 的反应路径。

  DOI：

  10.1246/bcsj.42.1345
• 作为产物：
  描述：

  n-butyl glycidyl ether 在 potassium cyanide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以81%的产率得到γ-Butoxy-β-hydroxy-butyronitril
  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

• 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。
• Synthesis and characterization of a novel Fe3O4@SiO2/bipyridinium dichloride nanocomposite and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols
  作者：Ali Reza Kiasat、Fatemeh Chadorian、Seyyed Jafar Saghanezhad

  DOI：10.1016/j.crci.2015.06.019

  日期：2015.12

  Résumé β-Azidoalcohols, β-cyanohydrins, and β-acetoxy alcohols have been synthesized in the presence of a Fe3O4@SiO2/bipyridinium nanocomposite (Fe3O4@SiO2/BNC) as a novel magnetic and recyclable phase-transfer catalyst (PTC) in water. The catalyst was characterized with FT–IR, SEM, XRD, VSM, and TGA. This methodology offers several advantages, including easy work-up procedure, excellent regioselectivity, high yields, short reaction times, recyclable catalyst, easy separation of the catalyst through an external magnet and eco-friendly procedure.

  摘要 β-叠氮醇、β-氰醇和 β-乙酰氧基醇在作为新型磁性可回收相转移催化剂（PTC）的 Fe3O4@SiO2/ 联吡啶纳米复合材料（ @SiO2/BNC）存在下于水中合成。该催化剂通过傅立叶变换红外光谱、扫描电镜、XRD、VSM 和热重分析进行了表征。该方法具有多个优点，包括操作简便、具有优异的区域选择性、产率高、反应时间短、催化剂可回收、催化剂易于通过外部磁铁分离以及操作过程环保。
• Greener and regioselective ring opening of epoxides with TMSCN using potassium salts of magnetic carbon nitride
  作者：Mostafa Saadat、Mahnaz Qomi、Najmedin Azizi

  DOI：10.1007/s00706-020-02689-0

  日期：2020.10

  green and recyclable catalyst for rapid and regioselective ring opening of epoxides with TMSCN, yielding the β-hydroxynitrile ring-opened products under mild reaction conditions. It is manageable to large-scale preparation with simple instruments and gives the desired compounds in short reaction times with good-to-excellent yields (73–95%) under solvent-free conditions. Magnetic separation protocol has

  摘要 磁性石墨碳氮化碳（Fe 3 O 4 @gC 3 N 4 -K）的钾盐经合成，被证明是一种绿色且可回收的催化剂，可用于通过TMSCN快速和区域选择性地使环氧化物开环，生成β-羟基腈开环产物在温和的反应条件下。使用简单的仪器即可进行大规模制备，并且在无溶剂条件下以较短的反应时间即可获得所需化合物，并具有良好至优异的收率（73–95％）。磁分离方案已使用外部磁体实现了从未纯化的反应混合物中简单分离和重复使用催化剂，而在五个循环后没有损失催化操作。 图形摘要
• Facile synthesis of an organic–inorganic nanocomposite, PEG–silica, by sol–gel method; its characterization and application as an efficient catalyst in regioselective nucleophilic ring opening of epoxides: Preparation of β-azido alcohols and β-cyanohydrins
  作者：Ali Reza Kiasat、Simin Nazari、Jamal Davarpanah

  DOI：10.1016/j.crci.2013.07.008

  日期：2014.2

  Abstract The sol–gel method was used for the synthesis of a PEG–silica hybrid. In order to introduce PEG into the cavities of silica gel, first, the bis(3-trimethoxysilylpropyl)-polyethylene glycol precursor was synthesized by the reaction of 3-chloropropyltrimethoxysilane with alkoxides formed on the PEG terminals. The organic–inorganic hybrid silica was then synthesized by hydrolysis and polycondensation

  摘要 溶胶-凝胶法用于合成 PEG-二氧化硅杂化物。为了将 PEG 引入硅胶空腔，首先通过 3-氯丙基三甲氧基硅烷与 PEG 末端形成的醇盐反应合成双（3-三甲氧基甲硅烷基丙基）-聚乙二醇前体。然后在弱酸性条件下通过前体的水解和缩聚合成有机-无机杂化二氧化硅。FT-IR、XRD 和 TGA 的特征结果证实了二氧化硅和 PEG 网络的共存。还研究了这种多相催化剂对 H 2 O 中叠氮化物和氰化物阴离子对环氧化物区域选择性开环的催化能力。