5-phenylpentyl benzoate | 1332887-12-3

• 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: 5-phenylpentyl benzoate
• CAS: 1332887-12-3
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: VRVXSWUMNFDYCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenylpentyl benzoate 在 N-羟基邻苯二甲酰亚胺 、 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 以81%的产率得到5-benzoyloxy-1-phenylpentyl nitrate
  参考文献：
  名称：

  Direct oxidative installation of nitrooxy group at benzylic positions and its transformation into various functionalities

  摘要：

  C-H Nitrooxylation at benzylic positions has been achieved by employing the N-hydroxyphthalimide (NHPI) catalyst/cerium(IV) ammonium nitrate (CAN) reagent system. The nitrooxy groups were demonstrated to function as tentative hydroxy protecting groups, as well as excellent leaving groups for N- and C-substitution reactions. Hence, the present method offers a unique way to synthesize diverse O-. N-, or C-functionalized benzylic compounds from simple alkyl aromatics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.118
• 作为产物：
  描述：

  碘苯 、 5-bromopentyl benzoate 在 吡啶 、 nickel(II) iodide 、 4,4'-二叔丁基-2,2'-二吡啶 、 magnesium chloride 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以30%的产率得到5-phenylpentyl benzoate
  参考文献：
  名称：

  镍催化的芳基卤化物与仲烷基溴化物和乙酸烯丙酯的还原偶联

  摘要：

  已经开发了一种室温镍催化的还原方法，用于将芳基溴化物与仲烷基溴化物偶合，从而以良好的收率提供了良好的C（sp 2）–C（sp 3）产品。对该协议进行轻微修改，即可使活化的芳基氯化物与环己基溴化物有效偶联，而芳基溴化物与乙酸烯丙酯有效偶联。

  DOI：

  10.1021/ol3013342

文献信息

• Enantioselective Intermolecular Radical Amidation and Amination of Benzylic C−H Bonds via Dual Copper and Photocatalysis
  作者：Xuemeng Chen、Zhong Lian、Søren Kramer

  DOI：10.1002/anie.202217638

  日期：2023.3.20

  A method for enantioselective intermolecular benzylic C−H amidation and amination is reported. This dehydrogenative C−N bond formation displays broad substrate scope and good atom economy, is amenable to late-stage C−H functionalization, and enables easy access to 15N-labeling from cheap [15N]-NH4Cl.

  报道了一种对映选择性分子间苄基 C−H 酰胺化和胺化的方法。这种脱氢 C−N 键形成显示出广泛的底物范围和良好的原子经济性，适用于后期 C−H 功能化，并且能够从廉价的 [ 15 N]-NH 4 Cl轻松获得15 N-标记。
• Metal-Free Fluorination of C(sp³)–H Bonds Using a Catalytic <i>N</i>-Oxyl Radical
  作者：Yuuki Amaoka、Masanori Nagatomo、Masayuki Inoue

  DOI：10.1021/ol4006757

  日期：2013.5.3

  A direct conversion of C(sp(3))-H bonds to C(sp(3))-F bonds has been developed. In this process, a catalytic N-oxyl radical generated from N,N-dihydroxypyromellitimide abstracts hydrogen from the C(sp(3))-H bond and Selectfluor acts to trap the resulting carbon radical to form the C(sp(3))-F bond. This simple metal-free protocol enables the chemoselective introduction of a fluorine atom into various aromatic and aliphatic compounds and serves as a powerful tool for the efficient synthesis of fluorinated molecules.
• US6919397B2
  申请人：——

  公开号：US6919397B2

  公开（公告）日：2005-07-19
• Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate
  作者：Shulin Wang、Qun Qian、Hegui Gong

  DOI：10.1021/ol3013342

  日期：2012.7.6

  A room-temperature Ni-catalyzed reductive method for the coupling of aryl bromides with secondary alkyl bromides has been developed, providing C(sp2)–C(sp3) products in good to excellent yields. Slight modification of this protocol allows efficient coupling of activated aryl chlorides with cyclohexyl bromide and aryl bromides with allylic acetate.

  已经开发了一种室温镍催化的还原方法，用于将芳基溴化物与仲烷基溴化物偶合，从而以良好的收率提供了良好的C（sp 2）–C（sp 3）产品。对该协议进行轻微修改，即可使活化的芳基氯化物与环己基溴化物有效偶联，而芳基溴化物与乙酸烯丙酯有效偶联。
• Direct oxidative installation of nitrooxy group at benzylic positions and its transformation into various functionalities
  作者：Shin Kamijo、Yuuki Amaoka、Masayuki Inoue

  DOI：10.1016/j.tetlet.2011.06.118

  日期：2011.9

  C-H Nitrooxylation at benzylic positions has been achieved by employing the N-hydroxyphthalimide (NHPI) catalyst/cerium(IV) ammonium nitrate (CAN) reagent system. The nitrooxy groups were demonstrated to function as tentative hydroxy protecting groups, as well as excellent leaving groups for N- and C-substitution reactions. Hence, the present method offers a unique way to synthesize diverse O-. N-, or C-functionalized benzylic compounds from simple alkyl aromatics. (C) 2011 Elsevier Ltd. All rights reserved.