2-(4-氟苯基)-2-苯基-乙腈 | 719-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氟苯基)-2-苯基-乙腈
• 英文名称: 2-(4-fluorophenyl)-2-phenylacetonitrile
• CAS: 719-82-4
• 化学式: C₁₄H₁₀FN
• 分子量: 211.239
• InChiKey: LRNPWSOSXVCRKG-UHFFFAOYSA-N

物化性质

• 熔点：
  39-41 °C
• 沸点：
  192 °C(Press: 25 Torr)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)-2-苯基-乙腈 在 吡啶 、 硫化氢 、 三乙胺 作用下， 反应 12.0h， 以68%的产率得到2-(4-Fluorophenyl)-2-phenylethanethioamide
  参考文献：
  名称：

  Histamine H1 receptor ligands

  摘要：

  New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H-1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H-1-antagonistic activity (pA(2): 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA(2) < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H-1-antagonistic activity (at the meta-position pA(2): 6.38-6.15; at the para-position pA(2): 6.04-5.87). (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00087-2
• 作为产物：
  描述：

  对氟苯乙腈 在 三氯化铝 、 溴 作用下， 以 苯 为溶剂， 反应 1.25h， 生成 2-(4-氟苯基)-2-苯基-乙腈
  参考文献：
  名称：

  Histamine H1 receptor ligands

  摘要：

  New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H-1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H-1-antagonistic activity (pA(2): 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA(2) < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H-1-antagonistic activity (at the meta-position pA(2): 6.38-6.15; at the para-position pA(2): 6.04-5.87). (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00087-2

文献信息

• Phenyl-substituted Normethadones: Synthesis and Pharmacology
  作者：T K N Mbela、J H Poupaert、J Cumps、C Moussebois、A Haemers、M Borloo、P Dumont

  DOI：10.1111/j.2042-7158.1995.tb05786.x

  日期：2011.4.12

  Phenyl-substituted normethadone derivatives were synthesized and their affinity (IC50) for opioid receptors was determined by displacement of the specific binding sites of [3H]sufentanyl on rat brain preparations. Substitution resulted in a decrease of affinity in-vitro. These results suggest that normethadone-like compounds may interact with the P subsite of the mu-opioid receptor and that the P subsite

  合成了苯基取代的去甲美沙酮衍生物，并通过在大鼠脑制剂中置换[3H]舒芬太尼的特异性结合位点，确定了它们对阿片样物质受体的亲和力（IC50）。替代导致体外亲和力降低。这些结果表明，去甲美沙酮样化合物可与μ阿片受体的P亚位相互作用，并且该P亚位具有严格定义的腔体形状，尺寸严格。
• Condensed heterocyclic compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05607939A1

  公开（公告）日：1997-03-04

  The compound ##STR1## wherein ring A represents a benzene ring; Ar represents an aromatic group; R.sup.1 and R.sup.2 independently represent hydrogen, acyl or hydrocarbon group or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom represent a nitrogen-containing heterocyclic group; m represents an integer of 1 to 6; n represents an integer of 2 to 3; ----- represents a single bond or a double bond; X stands for --O-- or --NR.sup.3 -- in which R.sup.3 represents hydrogen, acyl or hydrocarbon group where ----- is a single bond or .dbd.N-- where ----- is a double bond has excellent GnRH receptor antagonizing activity, calcium antagonizing and monoamine-uptake inhibiting activities and and value as a prophylactic/therapeutic drug for sex hormone-dependent diseases and for central nervous system diseases.

  化合物##STR1##，其中环A表示苯环；Ar表示芳香族基团；R.sup.1 和 R.sup.2 各自独立地表示氢、酰基或烃基，或者 R.sup.1 和 R.sup.2 与相邻的氮原子一起表示含氮杂环基团；m表示1至6的整数；n表示2至3的整数；-----表示单键或双键；X表示--O--或--NR.sup.3 --，其中R.sup.3 表示氢、酰基或烃基，当-----为单键时，或表示.dbd.N--，当-----为双键时，该化合物具有优异的GnRH受体拮抗活性、钙拮抗活性和单胺摄取抑制活性，并且具有预防/治疗性激素依赖性疾病和中枢神经系统疾病的价值。
• The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes
  作者：Masakazu Nambo、Muhammad Yar、Joel D. Smith、Cathleen M. Crudden

  DOI：10.1021/ol503213z

  日期：2015.1.2

  The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki–Miyaura cross coupling reaction followed by back-to-back C–H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted

  据报道，通过连续的钯催化的氯乙腈的芳基化反应，可以选择性合成多芳基化的乙腈。这三个芳基是通过Pd催化的Suzuki-Miyaura交叉偶联反应安装的，然后是背靠背的C-H芳基化反应，分三步提供三芳基乙腈，任何一步均不发生过度芳基化。三芳基乙腈产物可以转化为高度官能化的物质，包括四芳基甲烷。这种新策略可从简单易得的起始原料中快速获得各种不对称的三芳基和四芳基甲烷衍生物。
• Rapid and Simple Access to α-(Hetero)arylacetonitriles from <i>Gem</i>-Difluoroalkenes
  作者：Jun-Qi Zhang、Jiayue Liu、Dandan Hu、Jinyu Song、Guorong Zhu、Hongjun Ren

  DOI：10.1021/acs.orglett.1c04336

  日期：2022.1.21

  A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reaction, aqueous ammonia offers a “N” source for the “CN” reagent and entirely avoids the use of toxic cyanating reagents or metal catalysis. Hence, we

  开发了一种可扩展的偕二氟烯烃氰化为（杂）芳基乙腈衍生物的方法。该策略具有反应条件温和、产率高、底物范围广、官能团耐受性广等特点。值得注意的是，在该反应中，氨水为“CN”试剂提供了“N”源，并且完全避免使用有毒的氰化试剂或金属催化剂。因此，我们为芳基乙腈的合成提供了一种绿色替代方法。
• BF 3 ·OEt 2 -mediated [1,2]-aryl shift: Synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin
  作者：Chieh-Kai Chan、Meng-Yang Chang

  DOI：10.1016/j.tet.2017.07.015

  日期：2017.8

  A new sequential, tandem synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF3·OEt2 results in the formation of functionalized

  通过取代的脱氧安息香素的溴化/氰化/去甲酰基化，开发了一种新的顺序串联的官能化α-芳基腈的合成方法。CuBr 2促进的取代脱氧安息香素的溴化反应生成2-溴-2-芳基乙酰基3。的氰化3用氰化钠（NaCN的）epoxynitrile生成。然后，用BF 3 · OEt 2处理环氧腈导致通过1,2-芳基转移形成官能化的α-芳基腈4。