2,3-bis(4-fluorophenyl)propanenitrile | 144452-24-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3-bis(4-fluorophenyl)propanenitrile
• CAS: 144452-24-4
• 化学式: C₁₅H₁₁F₂N
• 分子量: 243.256
• InChiKey: CPTJPOPWOYEKIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-bis(4-fluorophenyl)propanenitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 2,3-bis(4-fluorophenyl)propanamine
  参考文献：
  名称：

  Synthesis and histamine H2 agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups

  摘要：

  Analogues of the potent histamine H-2 agonist arpromidine, characterized by non-heterocyclic groups (phenyl, cyclo-hexyl, alkyl) instead of the pheniramine-like portion, were prepared and tested for their H-2 agonistic and H-1 antagonistic activity in the isolated guinea pig right atrium and ileum, respectively. In the diphenylpropylguanidine series an increase in H-2 agonistic potency resulted from mono- or difluorination at one or both phenyl rings in the meta and/or para position (pD2 less-than-or-equal-to 7.75 vs pD2 = 7.15 for the unsubstituted parent compound). Compounds chlorinated at both phenyl rings were considerably less potent. Highest combined H-2 agonistic/H-1 antagonistic potency was found in the 4-fluorophenyl series. The arpromidine analogue with cyclohexyl and methyl group instead of phenyl and pyridine ring proved to be 30 times more potent than histamine in the atrium. The H-1 antagonistic potency in cyclohexyl compounds was lower than in the diaryl series. Thus, aromatic rings appear not to be required for high H-2 agonistic potency but are useful for combined H-2 agonistic/H-1 antagonistic activity.

  DOI：

  10.1016/0223-5234(92)90145-q
• 作为产物：
  描述：

  (Z)-2,3-bis(4-fluorophenyl)acrylonitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以91%的产率得到2,3-bis(4-fluorophenyl)propanenitrile
  参考文献：
  名称：

  Targeting Several Biologically Reported Targets of Glioblastoma Multiforme by Assaying 2D and 3D Cultured Cells

  摘要：

  DOI：

  10.1007/s10571-021-01072-9

文献信息

• 一种以甲酰胺为氰源的腈类化合物的制备方法
  申请人：湘潭大学

  公开号：CN110845364B

  公开（公告）日：2023-02-03

  本发明公开一种腈类化合物的制备方法，是在镍催化剂的作用下，以甲酰胺为氰源，与各种类型的烯烃发生氢氰化反应，生成各种腈类化合物；反应温度为60‑160℃，反应时间为6‑36小时。该方法克服了传统的烯烃的氢氰化反应存在的操作复杂，需要使用剧毒的氰源作为反应原料等不足。该方法使用简单廉价、绿色无毒的甲酰胺为氰基的来源，并且不需要另外加入其它的脱水剂(如：五氧化二磷、三氯氧磷等)，通过路易斯酸催化下甲酰胺的自发脱水生成氰基负离子，并原位与烯烃发生氢氰化反应，生成腈类化合物；反应条件简单、易于操作、经济高效；同时该方法适用于各种单取代、双取代的脂肪族和芳香族烯烃，展示出良好的底物普适性；对空气、水分、光均不敏感；产率高，产物分离纯化简单，有广泛的应用前景。
• Ni-Catalyzed hydrocyanation of alkenes with formamide as the cyano source
  作者：Xiao Shu、Yuan-Yuan Jiang、Lei Kang、Luo Yang

  DOI：10.1039/c9gc04275j

  日期：——

  “CN” generation from formamide dehydration! A novel Ni-catalyzed hydrocyanation of various alkenes to provide aliphatic nitriles is developed by generating hydrocyanic acid in situ from safe and readily available formamide. Excellent linear or branched regio-selectivity, wide substrate scope, cheap and stable nickel salt as a pre-catalyst, a safe cyano source, slow generation of “CN” to obviate catalyst

  甲酰胺脱水生成“ CN”！通过从安全易得的甲酰胺中原位生成氢氰酸，开发了各种烯烃的新型Ni催化氢氰化反应，以提供脂肪族腈。优异的线性或支链区域选择性，广泛的底物范围，廉价且稳定的镍盐作为预催化剂，安全的氰基源，缓慢生成的“ CN”可避免催化剂失活以及方便的实验操作，使得这种氢氰化作用对于实验室合成而言是无活性的脂肪腈。
• Nickel/Cobalt‐Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent
  作者：Jin Zhang、Cui‐Ping Luo、Luo Yang

  DOI：10.1002/adsc.202000935

  日期：2021.1.5

  A Ni/Co co‐catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the NiII pre‐catalyst and vinyl nitriles, along with acting as the co‐solvent in this reaction. Detailed mechanistic investigation

  开发了一种Ni / Co共催化的各种炔烃的还原性氢氰化反应，用于生产饱和腈。氢氰酸是从安全易得的甲酰胺中原位生成的。甲酰胺在Ni II预催化剂和乙烯基腈中起氰基源，脱水剂和还原剂的作用，并在该反应中作为助溶剂。详细的机理研究支持了通过C≡C键氢氰化和随后C = C键还原的途径。广泛的底物范围，使用便宜且稳定的镍盐作为前催化剂，安全的氰基来源和方便的实验操作使这种氢氰化法在实验室合成饱和腈方面具有实用性。
• Chemoselective <i>α</i>‐Alkylation of Nitriles with Primary Alcohols by Manganese(I)‐Catalysis
  作者：Krishanu Bera、Arup Mukherjee

  DOI：10.1002/asia.202300157

  日期：2023.7.3

  Sustainable Alkylation: A simple and easy-to-use manganese(I) catalyzed sustainable alkylation of aryl nitrile with alcohols is reported. The reaction proceeds with broad substrate scope. Controlled experiments were conducted to understand the mechanism.

  可持续烷基化：报道了一种简单易用的锰（I）催化芳基腈与醇的可持续烷基化反应。该反应在广泛的底物范围内进行。进行对照实验以了解其机制。