4-phenoxy-ξ-crotononitrile | 103261-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-phenoxy-ξ-crotononitrile
• 英文别名: 3-Cyano allyl phenyl ether；4-phenoxybut-2-enenitrile
• CAS: 103261-28-5
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: JLKORMLNNNKMCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二氟溴乙酸乙酯 、 4-phenoxy-ξ-crotononitrile 在 铜 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以57%的产率得到ethyl 4-cyano-2,2-difluoro-3-(butoxymethyl)butanoate
  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
• 作为产物：
  描述：

  3-羟基-4-苯氧基丁腈 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以53%的产率得到4-phenoxy-ξ-crotononitrile
  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

• Nickel-catalyzed regioselective hydrocyanation of terminal alkynes by assistance of a tosyl group
  作者：Shigeru Arai、Koichi Nakazawa、Xiao-fei Yang、Atsushi Nishida

  DOI：10.1016/j.tet.2019.03.019

  日期：2019.4

  hydrocyanation of terminal alkynes is described. A tosylamide functionality at the propargyl position was the most suitable group for controlling the regiochemistry for CCN bond formation as well as rate enhancement. A gram-scale synthesis was achieved by minimizing the catalyst loading to 2 mol%. The major HCN adduct could be transformed to the corresponding indoline through construction of a benzylic quaternary

  描述了末端炔烃的镍催化的区域选择性氢氰化。炔丙基位置上的甲苯磺酰胺官能团是最合适的基团，用于控制区域化学以形成C CN键以及提高速率。通过将催化剂载量最小化至2mol％来实现克级合成。通过在铁催化下构建苄基季碳，可以将主要的HCN加合物转化为相应的二氢吲哚。
• van der Straeten; Bruylants, Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 345,355,362
  作者：van der Straeten、Bruylants

  DOI：——

  日期：——
• Julia, Bulletin de la Societe Chimique de France, 1954, p. 474,477
  作者：Julia

  DOI：——

  日期：——
• Synthesis of 4-Substituted 3,3-Difluoropiperidines
  作者：Riccardo Surmont、Guido Verniest、Jan Willem Thuring、Gregor Macdonald、Frederik Deroose、Norbert De Kimpe

  DOI：10.1021/jo902164z

  日期：2010.2.5

  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.