1-phenylethyl picolinate | 1309438-64-9

• 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: 1-phenylethyl picolinate
• 英文别名: (rac)-1-phenylethanol picolinic acid ester；rac-1-phenylethyl picolinate；1-Phenylethyl pyridine-2-carboxylate；1-phenylethyl pyridine-2-carboxylate
• CAS: 1309438-64-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: KXPFJGOBCQPUKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylethyl picolinate 在 甲醇 、 (CH₃N₂C₃H₂CHNC₆H₁₀NHSO₂C₆H₄CH₃)ZnCl₂ 作用下， 以 氘代甲醇 、 二氯甲烷-D2 为溶剂， 生成 苏合香醇
  参考文献：
  名称：

  New chiral Schiff base–zinc complexes and their esterolytic catalytic activity

  摘要：

  A new series of chiral Zn-Schiff base (imine) complexes has been prepared from mono-N-sulfonyl derivatives of (1R,2R)-diaminocyclohexane, N-heterocyclic aldehydes, and zinc salts. The formation and characterization of the (L)ZnX2 complexes was established by NMR. IR and HRESI-MS. Spectroscopic and kinetic evidence indicates that these ligands may be bidentate or tridentate depending on conditions of the medium. The methanolysis of a chiral, racemic picolinate ester catalyzed by the Zn(II)-Schiff base complexes was studied kinetically. The rate constants were found to vary approximately a hundred-fold and in a complex way depending on the imine ligand and the Zn-counter anion, k(obs) =5.0 x 10(-6)-4.8 x 10(-4) M-1 s(-1). A Job plot analysis of ternary complex formation of LZnX2 with two phosphonate transition state analogs suggests that two types of (imine)Zn(picolinate)X ternary complexes may be intermediates and that varying rate-limiting steps may be involved in the LZnX2-catalyzed methanolysis of picolinate esters. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.02.014
• 作为产物：
  描述：

  2-吡啶甲酸 、 苏合香醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以86%的产率得到1-phenylethyl picolinate
  参考文献：
  名称：

  通过 FeCl3 催化吡啶甲酸酯定向芳烃间位 CH 胺化

  摘要：

  芳香族化合物的直接 CH 官能化是有机合成的有力工具；然而，在普遍存在且通常化学上相似的 CH 键之间进行区分仍然是一个重大挑战。尽管对远程站点的访问仍然有限，但与合并到预期基板中的协调或指导组的合并有助于解决这些限制。在此，我们报告了一种操作简单且可持续的直接间位选择性 H2N 胺化，在足够温和的条件下对苄基和相关芳香族吡啶甲酸酯进行修饰，以修饰多功能和后期分子。

  DOI：

  10.1021/jacs.9b13753

文献信息

• A Metal-Free Oxidative Esterification of the Benzyl CH Bond
  作者：Jie Feng、Shuai Liang、Shan-Yong Chen、Ji Zhang、Song-Sen Fu、Xiao-Qi Yu

  DOI：10.1002/adsc.201100920

  日期：2012.5.7

  An efficient metal‐free oxidative esterification of benzyl CH bonds was developed. Using tetrabutylammonium iodide as catalyst and tert‐butyl hydroperoxide as co‐oxidant, benzylic substrates could react smoothly with various carboxylic acids to give the esters with good to excellent yields. The method was also suitable for the O‐protection of N‐Boc amino acids. The reaction mechanism was primarily

  的苄℃的高效无金属氧化酯化 H键被开发。使用四丁基碘化铵作为催化剂，叔丁基过氧化氢作为助氧化剂，苄基底物可以与各种羧酸平稳地反应，从而以良好或优异的收率得到酯。该方法也适用于N- Boc氨基酸的O-保护。初步研究了反应机理并提出了自由基反应方法。
• Picolinate-Directed Arene <i>meta</i>-C–H Amination via FeCl₃ Catalysis
  作者：Raghunath Reddy Anugu、Sailu Munnuri、John R. Falck

  DOI：10.1021/jacs.9b13753

  日期：2020.3.18

  Direct C-H functionalization of aromatic compounds is a powerful tool for organic synthesis; however, differentiation amongst the ubiquitous and often chemically similar C-H bonds remains a significant challenge. Conflation with coordinating or directing groups incorporated into the intended substrate has helped address these limitations, although access to remote sites remains limited. Herein, we

  芳香族化合物的直接 CH 官能化是有机合成的有力工具；然而，在普遍存在且通常化学上相似的 CH 键之间进行区分仍然是一个重大挑战。尽管对远程站点的访问仍然有限，但与合并到预期基板中的协调或指导组的合并有助于解决这些限制。在此，我们报告了一种操作简单且可持续的直接间位选择性 H2N 胺化，在足够温和的条件下对苄基和相关芳香族吡啶甲酸酯进行修饰，以修饰多功能和后期分子。
• New chiral Schiff base–zinc complexes and their esterolytic catalytic activity
  作者：Ramu Kannappan、Masaomi Matsumoto、John Hallren、Kenneth M. Nicholas

  DOI：10.1016/j.molcata.2011.02.014

  日期：2011.4

  A new series of chiral Zn-Schiff base (imine) complexes has been prepared from mono-N-sulfonyl derivatives of (1R,2R)-diaminocyclohexane, N-heterocyclic aldehydes, and zinc salts. The formation and characterization of the (L)ZnX2 complexes was established by NMR. IR and HRESI-MS. Spectroscopic and kinetic evidence indicates that these ligands may be bidentate or tridentate depending on conditions of the medium. The methanolysis of a chiral, racemic picolinate ester catalyzed by the Zn(II)-Schiff base complexes was studied kinetically. The rate constants were found to vary approximately a hundred-fold and in a complex way depending on the imine ligand and the Zn-counter anion, k(obs) =5.0 x 10(-6)-4.8 x 10(-4) M-1 s(-1). A Job plot analysis of ternary complex formation of LZnX2 with two phosphonate transition state analogs suggests that two types of (imine)Zn(picolinate)X ternary complexes may be intermediates and that varying rate-limiting steps may be involved in the LZnX2-catalyzed methanolysis of picolinate esters. (C) 2011 Elsevier B.V. All rights reserved.