3-hydroxy-6-heptenenitrile | 70102-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-6-heptenenitrile
• 英文别名: 3-hydroxyhept-6-enenitrile
• CAS: 70102-86-2
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: NBDYMSGNVSUIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Bromo-5-(but-3-EN-1-YL)-4,5-dihydro-1,2-oxazole 在 对甲苯磺酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以90%的产率得到3-hydroxy-6-heptenenitrile
  参考文献：
  名称：

  Ring Opening of 3‐Bromo‐2‐Isoxazolines to β‐Hydroxy Nitriles

  摘要：

  3-Bromo-2-isoxazolines were converted to the corresponding beta-hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para-toluenesulfonic acid. Both methods gave beta-hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3-bromo-2-isoxazolines.

  DOI：

  10.1081/scc-200039452

文献信息

• Metal(II) Schiff base complexes as catalysts for the high-regioselective conversion of epoxides to β-hydroxy nitriles in glycol solvents
  作者：Hossein Naeimi、Mohsen Moradian

  DOI：10.1139/v06-158

  日期：2006.11.1

  A facile preparation of 3-hydroxy propanenitrile derivatives is described involving ring opening of epoxides with potassium cyanide in glycol solvents in the presence of Schiff base complexes as catalysts. This method occurs under neutral and mild conditions with high yields and high regioselectivity. Thus, several β-Hydroxy nitriles, useful intermediates toward biologically-active molecules, are easily obtained at room temperature.Key words: β-hydroxy nitrile, Schiff base, epoxide, glycol, catalyst.

  本文介绍了一种简便的 3-羟基丙腈衍生物制备方法，该方法涉及环氧化物与氰化钾在乙二醇溶剂中，在希夫碱络合物作为催化剂存在下的开环反应。该方法在中性温和的条件下进行，具有高产率和高区域选择性。因此，可在室温下轻松获得几种 β-羟基腈，它们是生物活性分子的有用中间体。
• Facile conversion of epoxides to β-hydroxy nitriles under anhydrous conditions with lithium cyanide
  作者：James A. Ciaccio、Catherine Stanescu、Jongnic Bontemps

  DOI：10.1016/s0040-4039(00)91639-3

  日期：1992.3

  Functionalized epoxides are easily and efficiently converted to β-hydroxy nitriles in good yield with high regio- and stereoselectivity upon treatment with lithium cyanide in refluxing anhydrous THF. The conditions described permit a one-pot conversion of epoxide to 1,3-amino alcohol via hydride reduction of the nitrile.

  在回流的无水THF中用氰化锂处理后，官能化的环氧化物可以轻松，有效地以高收率和高选择性以及高选择性转化为β-羟基腈。所描述的条件允许通过腈的氢化物还原将环氧一锅转化为1,3-氨基醇。
• Synthesis of β-hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as a LiCN precursor
  作者：James A. Ciaccio、Michael Smrtka、William A. Maio、David Rucando

  DOI：10.1016/j.tetlet.2004.08.039

  日期：2004.9

  The reaction of acetone cyanohydrin with MeLi affords a LiCN·acetone complex that can be made to react with epoxides in THF, either in one-pot or using isolated samples of the cyanide complex, to cleanly afford β-hydroxy nitriles upon aqueous workup; in situ hydride reduction of nitriles affords 1,3-amino alcohols.

  丙酮氰醇与MeLi的反应可制得LiCN·丙酮络合物，可将其与THF中的环氧化物反应，可以一锅法或使用氰化物络合物的分离样品，经水后处理干净地得到β-羟基腈。原位氢化还原腈可得到1,3-氨基醇。
• [EN] PYRAZOLO[1,5-A]PYRAZINE DERIVATIVES AS BTK INHIBITORS<br/>[FR] DÉRIVÉS DE PYRAZOLO[1,5-A]PYRAZINE UTILISÉS EN TANT QU'INHIBITEURS DE BTK
  申请人：BIOGEN MA INC

  公开号：WO2022104079A1

  公开（公告）日：2022-05-19

  Provided are compounds of Formula (I'): or pharmaceutically acceptable salts thereof, wherein the variables in the formula are as defined herein; and methods for their use and production.

  提供了公式（I'）的化合物或其药学上可接受的盐，其中公式中的变量如此处定义；以及它们的使用和生产方法。
• Preparation and reactivity of acetoacetonitrile dianion
  作者：Fredric J. Vinick、Yolanda Pan、Heinz W. Gschwend

  DOI：10.1016/s0040-4039(01)95186-x

  日期：1978.1