1-(4-(9-isopropyl-9H-purin-6-yl)phenyl)ethan-1-one | 1535484-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(9-isopropyl-9H-purin-6-yl)phenyl)ethan-1-one
• CAS: 1535484-13-9
• 化学式: C₁₆H₁₆N₄O
• 分子量: 280.329
• InChiKey: JMWPLAFQBKZTBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5-二氧代-1-吡咯烷甲腈 、 1-(4-(9-isopropyl-9H-purin-6-yl)phenyl)ethan-1-one 在 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 、 silver(I) acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以48%的产率得到
  参考文献：
  名称：

  N-氰基琥珀酰亚胺作为新型氰化剂的钴催化（杂）芳烃和6-芳基嘌呤的CHH氰化反应

  摘要：

  使用N-氰基琥珀酰亚胺作为新型的亲电子氰化剂，已开发出钴催化芳烃的CH氰化反应。反应以高选择性进行，得到具有优异的官能团耐受性的单氰酸酯化产物。发现底物的范围足够宽，可以包括包括6-芳基嘌呤在内的各种杂环。

  DOI：

  10.1021/ol503680d

文献信息

• Cp*Co^III-Catalyzed Dehydrative C–H Allylation of 6-Arylpurines and Aromatic Amides Using Allyl Alcohols in Fluorinated Alcohols
  作者：Youka Bunno、Nanami Murakami、Yudai Suzuki、Motomu Kanai、Tatsuhiko Yoshino、Shigeki Matsunaga

  DOI：10.1021/acs.orglett.6b00846

  日期：2016.5.6

  Cp*CoIII-catalyzed C–H allylation of various aromatic C–H bonds using allyl alcohols as allylating reagents is described. Improved reaction conditions using fluorinated alcohol solvents afforded efficient directed C–H allylation of 6-arylpurines, benzamides, and a synthetically useful Weinreb amide with good functional group compatibility.

  描述了使用烯丙醇作为烯丙基化试剂的Cp * Co III催化的各种芳香族CH-H键的CH-H烯丙基化。使用氟化醇溶剂改善的反应条件提供了6-芳基嘌呤，苯甲酰胺和具有良好官能团相容性的合成有用的Weinreb酰胺的有效的定向C–H烯丙基化。
• Ruthenium(II)-Catalyzed <i>meta</i> C−H Mono- and Difluoromethylations by Phosphine/Carboxylate Cooperation
  作者：Zhixiong Ruan、Shou-Kun Zhang、Cuiju Zhu、Paul Niklas Ruth、Dietmar Stalke、Lutz Ackermann

  DOI：10.1002/anie.201611595

  日期：2017.2.13

  Ruthenium(II)‐catalyzed meta‐selective C−H (di)fluoromethylation was accomplished by phosphine and carboxylate cooperation. The remote C−H functionalization was characterized by ample substrate scope, thereby setting the stage for meta‐(di)fluoromethylation through facile C−H cleavage.

  钌（II） -催化的元-选择性C-H（二）氟甲基化是由膦和羧酸合作来实现的。远程CH官能化的特征是具有足够的底物范围，从而通过容易的CH裂解为间-（二）氟甲基化奠定了基础。
• Synthesis of Fluorine-Containing 6-Arylpurine Derivatives &lt;i&gt;via&lt;/i&gt; Cp*Co(III)-Catalyzed C–H Bond Activation
  作者：Nanami Murakami、Misaki Yoshida、Tatsuhiko Yoshino、Shigeki Matsunaga

  DOI：10.1248/cpb.c17-00797

  日期：——

  Cp*Co(III)-catalyzed (Cp*=pentamethylcyclopentadienyl) C–H bond functionalization of 6-arylpurines using gem-difluoroalkenes and allyl fluorides is described. The reaction with gem-difluoroalkenes afforded monofluoroalkenes with high (Z)-selectivity, while the reaction with allyl fluorides led to C–H allylation in moderate (Z)-selectivity. Both reactions proceeded using a user-friendly single-component catalyst [Cp*Co(CH3CN)3](SbF6)2 in fluorinated alcohol solvents without any additives. Robustness was also demonstrated by a preparative-scale reaction under air.

  本研究描述了 Cp*Co(III)-catalyzed (Cp*=pentamethylcyclopentadienyl) C-H bond functionalization of 6-arylpurines using gem-difluoroalkenes and allyl fluorides。与宝石二氟烯烃的反应以高 (Z) 选择性生成单氟烯烃，而与烯丙基氟化物的反应则以中等 (Z) 选择性生成 C-H 烯丙基化。这两个反应都是使用方便的单组分催化剂 [Cp*Co(CH3CN)3](SbF6)2，在氟化醇溶剂中进行的，没有使用任何添加剂。在空气中进行的制备规模反应也证明了其稳定性。
• Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group
  作者：Hyun Jin Kim、Manjaly J. Ajitha、Yongjae Lee、Jaeyune Ryu、Jin Kim、Yunho Lee、Yousung Jung、Sukbok Chang

  DOI：10.1021/ja4118472

  日期：2014.1.22

  We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group.