3-环己基-3-羟基-2-亚甲基丙腈 | 106011-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-环己基-3-羟基-2-亚甲基丙腈
• 英文名称: 3-cyclohexyl-3-hydroxy-2-methylenepropanenitrile
• 英文别名: 2-(1-hydroxycyclohexyl)acrylonitrile；2-(1-Hydroxycyclohexyl)prop-2-enenitrile
• CAS: 106011-29-4
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: FJTMCBYCOOSDCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  环己酮 、 丙烯腈 在 三乙烯二胺 作用下， 25.0 ℃ 、500.0 MPa 条件下， 反应 16.67h， 以50%的产率得到3-环己基-3-羟基-2-亚甲基丙腈
  参考文献：
  名称：

  Functionalisation of the α position of acrylate systems by the addition of carbonyl compounds: Highly pressure-dependent reactions.

  摘要：

  DOI：

  10.1016/s0040-4039(00)85119-9

文献信息

• Process for the preparation of 2-(hydroxyalkyl)acrylic compounds
  申请人：STAMICARBON B.V.

  公开号：EP0196708A1

  公开（公告）日：1986-10-08

  The invention relates to a process for the preparation of 2-(hydroxyalkyl)acrylic compounds having the formula wherein X represents a -CN group, a -COOR3 group, a - COR4 group or a -CONR4R5 group wherein R3 is an alkyl group containing 1-4 C atoms and R4 and Rs independently represent an H atom or R3, and wherein R, and R, independently represent an H atom or an alkyl group with 1-4 C atoms or an (hetero) aryl group, or R, and R2 together represent a cyclic compound with 5-12 C atoms by contacting an acrylic compound H2C = CH -X with a carbonyl compound of the formula wherein X, R, and R2 denote the same as in the above, this being effected in the liquid phase in the presence of a tertiary amine, characterized in that the reaction is carried out at a pressure in excess of 500 bar, advantageously 1,500-18,000 bar.

  本发明涉及一种制备 2-(羟基烷基)丙烯酸化合物的工艺，其式为 其中 X 代表-CN 基团、-COR3 基团、-COR4 基团或-CONR4R5 基团，其中 R3 是含有 1-4 个 C 原子的烷基，R4 和 Rs 独立地代表 H 原子或 R3，R 和 R 独立地代表 H 原子或含有 1-4 个 C 原子的烷基或（杂）芳基，或 R 和 R2 一起代表含有 5-12 个 C 原子的环状化合物。 其中 X、R 和 R2 表示与上述相同，在液相中在叔胺存在下进行，其特征在于反应是在超过 500 巴的压力下进行的，最好是 1,500-18,000 巴。
• Hill, Jon S.; Isaacs, Neil S., Journal of Chemical Research, Miniprint, 1988, # 10, p. 2641 - 2676
  作者：Hill, Jon S.、Isaacs, Neil S.

  DOI：——

  日期：——
• Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)₂ Using Water as the Hydrogen Source
  作者：Xingjie Zhang、Xin Xie、Yuanhong Liu

  DOI：10.1021/jacs.8b02542

  日期：2018.6.20

  The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)(2) in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
• JACKSON, W. ROY;LOVEL, CRAIG G.;PERLMUTTER, PATRICK;SMALLRIDGE, ANDREW J., AUSTRAL. J. CHEM., 41,(1988) N, C. 1099-1106
  作者：JACKSON, W. ROY、LOVEL, CRAIG G.、PERLMUTTER, PATRICK、SMALLRIDGE, ANDREW J.

  DOI：——

  日期：——
• HILL, JON S.;ISAACS, NEIL S., J. CHEM. RES. (S),(1988) N 10, C. 330-331
  作者：HILL, JON S.、ISAACS, NEIL S.

  DOI：——

  日期：——