4-(2-苯基乙基)苯甲腈 | 10270-27-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-(2-苯基乙基)苯甲腈
• 英文名称: 4-phenethylbenzonitrile
• 英文别名: 4-(2-phenylethyl) benzonitrile；1-(4-cyanophenyl)-2-phenylethane；4-(2-Phenylethyl)benzonitrile
• CAS: 10270-27-6
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: HMQUZFVNFHUENY-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：
  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：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-苯基乙基)苯甲腈 在 盐酸 、 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 盐酸羟胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Structure–activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors

  摘要：

  Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.03.041
• 作为产物：
  描述：

  4-cyanostilbene 在 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到4-(2-苯基乙基)苯甲腈
  参考文献：
  名称：

  硅藻土-聚苯胺负载的钯催化剂用于化学选择性加氢反应

  摘要：

  涂覆在硅藻土颗粒上的聚苯胺被用作负载钯催化剂的载体。这种杂化的Celite•PANI•Pd系统被用作化学选择性氢化反应的有效催化剂。该催化剂通过常用的光谱，分析技术进行表征，并针对环境条件下的氢化反应进行了研究。温和的反应条件可以控制反应，并在转化数上实现出色的选择性。碳-碳双键的氢化作用优于其他极性π-键系统，而不稳定的官能团（如苄基醚，苄基酯，氰基，硝基和卤素）不受影响。伯胺被转化为N，N‐二甲基胺与甲醛，香豆素的双键被选择性地氢化而不打开内酯官能团。

  DOI：

  10.1002/aoc.4767

文献信息

• Development of the Direct Suzuki–Miyaura Cross-Coupling of Primary <i>B</i>-Alkyl MIDA-boronates and Aryl Bromides
  作者：Jeffrey D. St. Denis、Conor C. G. Scully、C. Frank Lee、Andrei K. Yudin

  DOI：10.1021/ol500057a

  日期：2014.3.7

  The development of a palladium-catalyzed sp3–sp2 Suzuki–Miyaura cross-coupling of B-alkyl-N-methyliminodiacetyl (B-alkyl MIDA) boronates and (hetero)aryl bromides is reported. This transformation is tolerant of a variety of functional groups (F, NO2, CN, Cl, COCH3, and CHO). B-Alkyl MIDA boronates allow an efficient cross-coupling reaction directed toward the synthesis of unsymmetrical methylene diaryls

  发展的钯-催化的SP 3 -SP 2铃木-宫浦交叉偶合B-烷基Ñ -methyliminodiacetyl（乙-烷基MIDA）硼酸酯和（杂）芳基溴化物进行报告。这种转化耐受各种官能团（F，NO 2，CN，Cl，COCH 3和CHO）。B-烷基MIDA硼酸酯可实现高效的交叉偶联反应，以高收率或优异收率合成不对称的亚甲基二芳基以及烷基化的芳烃。
• Efficient phosphine-mediated formal C(sp³)–C(sp³) coupling reactions of alkyl halides in batch and flow
  作者：U. P. N. Tran、K. J. Hock、C. P. Gordon、R. M. Koenigs、T. V. Nguyen

  DOI：10.1039/c7cc02033c

  日期：——

  transformation in synthetic chemistry due to its abundance in organic scaffolds. Here we demonstrate a valuable adaptation of the Wittig-type chemical procedure to efficiently facilitate C(sp3)–C(sp3) bond formation utilizing a range of alkyl building blocks. Additionally the method is amenable with flow synthesis to afford coupled products in good to excellent yields without laborious purification process

  由于C（sp 3）–C（sp 3）键在有机支架中的丰度，因此它是合成化学中必不可少的化学转化。在这里，我们展示了Wittig型化学程序的宝贵改编，以利用一系列烷基构件有效地促进C（sp 3）–C（sp 3）键的形成。另外，该方法适用于流动合成，以提供产率高至优异的偶联产物，而无需费力的纯化过程。
• Cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides
  作者：Gary A. Molander、Chang-Soo Yun

  DOI：10.1016/s0040-4020(02)00009-1

  日期：2002.2

  The cross-coupling reactions of primary alkylboronic acids with aryl triflates and aryl halides has been successfully achieved using PdCl2(dppf)·CH2Cl2 in the presence of potassium carbonate to provide the corresponding Suzuki coupled products in high yields.

  在碳酸钾存在下，使用PdCl 2（dppf）·CH 2 Cl 2成功地实现了伯烷基硼酸与芳基三氟甲磺酸酯和芳基卤化物的交叉偶联反应，从而以高收率提供了相应的Suzuki偶联产物。
• Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides
  作者：Peng Wang、Xuan-Di Song、Bing-Zhi Chen、Weidong Rao、Zhi-Liang Shen

  DOI：10.1016/j.catcom.2019.105824

  日期：2019.12

  The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important

  发现通过催化量的溴化钴（II）（10mol％）可有效地催化将铟粉直接插入到烷基碘中。使如此形成的烷基铟化合物与钯与多种芳基卤化物进行交叉偶联反应后，可以以中等到良好的产率获得一系列交叉偶联的产物，并且对许多重要的官能团具有耐受性。
• Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions
  作者：Man-Ling Zhi、Bing-Zhi Chen、Wei Deng、Xue-Qiang Chu、Teck-Peng Loh、Zhi-Liang Shen

  DOI：10.1021/acs.joc.9b00204

  日期：2019.3.1

  means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate

  报道了一种通过碘催化的将铟直接插入到THF中的烷基碘中来合成烷基铟试剂的有效方法。如此生成的烷基铟试剂可有效地与各种芳基卤化物进行Pd催化的交叉偶联反应，表现出与各种敏感官能团的良好相容性。通过用DMA代替THF并使用0.75当量的碘，同等容易程度的反应性较低的烷基溴可以用作铟插入的底物。