2-(4-fluorophenyl)-2-cyclohexylacetonitrile | 141528-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-fluorophenyl)-2-cyclohexylacetonitrile
• 英文别名: 2-Cyclohexyl-2-(4-fluorophenyl)acetonitrile
• CAS: 141528-95-2
• 化学式: C₁₄H₁₆FN
• 分子量: 217.286
• InChiKey: OLKDNKNCMTXUJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-fluorophenyl)-2-cyclohexylacetonitrile 在 二甲基硫 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以56%的产率得到2-(4-fluorophenyl)-2-cyclohexylethylamine
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017
• 作为产物：
  描述：

  溴代环己烷 、 对氟苯乙腈 在 lithium hexamethyldisilazane 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 16.5h， 生成 2-(4-fluorophenyl)-2-cyclohexylacetonitrile
  参考文献：
  名称：

  前手性α,α-二取代醛烯醇化物的对映选择性铑催化烯丙基烷基化用于构建无环四元立体中心

  摘要：

  描述了前手性 α,α-二取代醛烯醇化物与苯甲酸烯丙酯的高度对映选择性铑催化烯丙基烷基化。该协议为合成无环季碳立体中心提供了一种新方法，它代表了醛烯醇本身直接对映选择性烷基化的第一个例子。α-季醛产品的多功能性通过将它们转化为各种适用于靶向合成的有用基序来证明。最后，机理研究表明，前手性 (E)- 和 (Z)- 烯醇化物的混合物可实现高水平的不对称诱导，这为此类转化提供了令人兴奋的发展。

  DOI：

  10.1021/jacs.6b10099

文献信息

• 10.1021/acscatal.4c01383
  作者：Li, Tianyu、Da, Yue-Yi、Chen, Jing、Ma, Zongyan、Jin, Yu、Ma, Jiantai、Li, Rong

  DOI：10.1021/acscatal.4c01383

  日期：——

  bimetallic heterogeneous catalyst is presented for α-olefination and α-alkylation of nitriles using secondary alcohols. Currently, catalysis for this reaction has been exclusively carried out with homogeneous catalysts, which generally achieve satisfactory yields but come with some drawbacks, including challenging recovery processes and limited characterization methods. In contrast, this heterogeneous catalyst

  提出了一种采用 Ru-Fe 双金属非均相催化剂的催化策略，用于使用仲醇对腈进行 α-烯化和 α-烷基化。目前，该反应的催化仅使用均相催化剂进行，通常可以达到令人满意的收率，但也存在一些缺点，包括具有挑战性的回收过程和有限的表征方法。相比之下，这种多相催化剂不仅简化了回收，可以重复使用五个周期，而且与现有均相催化剂所达到的α-乙烯基腈产率相匹配。此外，该催化剂可以在不同的碱性条件下对α-烯烃化或α-烷基化腈的生产进行一定的控制。这项工作不仅扩展了使用仲醇合成β-二取代乙烯基腈的催化体系，而且展示了多相催化剂在无受体脱氢偶联中拓宽醇的范围的潜力，展示了双金属体系在增强有机合成中的作用。
• New triazine derivatives as potent modulators of multidrug resistance
  作者：Alain Dhainaut、Gilbert Regnier、Ghanem Atassi、Alain Pierre、Stephane Leonce、Laurence Kraus-Berthier、Jean Francois Prost

  DOI：10.1021/jm00091a017

  日期：1992.6

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.
• Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers
  作者：Timothy B. Wright、P. Andrew Evans

  DOI：10.1021/jacs.6b10099

  日期：2016.11.30

  highly enantioselective rhodium-catalyzed allylic alkylation of prochiral α,α-disubstituted aldehyde enolates with allyl benzoate is described. This protocol provides a novel approach for the synthesis of acyclic quaternary carbon stereogenic centers and it represents the first example of the direct enantioselective alkylation of an aldehyde enolate per se. The versatility of the α-quaternary aldehyde

  描述了前手性 α,α-二取代醛烯醇化物与苯甲酸烯丙酯的高度对映选择性铑催化烯丙基烷基化。该协议为合成无环季碳立体中心提供了一种新方法，它代表了醛烯醇本身直接对映选择性烷基化的第一个例子。α-季醛产品的多功能性通过将它们转化为各种适用于靶向合成的有用基序来证明。最后，机理研究表明，前手性 (E)- 和 (Z)- 烯醇化物的混合物可实现高水平的不对称诱导，这为此类转化提供了令人兴奋的发展。