methyl 2-(4-methoxybenzyl)-2-methylpropanoate | 1228320-14-6

• 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: methyl 2-(4-methoxybenzyl)-2-methylpropanoate
• 英文别名: 4-Fluoro-α,α-dimethylbenzenepropanoic acid, methyl ester；Methyl 3-(4-fluorophenyl)-2,2-dimethylpropanoate；methyl 3-(4-fluorophenyl)-2,2-dimethylpropanoate
• CAS: 1228320-14-6
• 化学式: C₁₂H₁₅FO₂
• 分子量: 210.248
• InChiKey: LYOBODQRZRXUME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-methoxybenzyl)-2-methylpropanoate 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(4-fluorophenyl)-2,2-dimethyl-N-(quinolin-8-yl)propanamide
  参考文献：
  名称：

  β-Arylation of Carboxamides via Iron-Catalyzed C(sp³)–H Bond Activation

  摘要：

  A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.

  DOI：

  10.1021/ja402806f
• 作为产物：
  描述：

  异丁酸甲酯 、 4-氟溴苄 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 methyl 2-(4-methoxybenzyl)-2-methylpropanoate
  参考文献：
  名称：

  铜催化的分子内C（sp3）？H和C（sp2）？氧化环化H酰胺化

  摘要：

  第一铜催化的分子内C（SP 3） H和（SPç 2） ħ氧化酰胺化得到了发展。在二氯乙烷溶剂中使用Cu（OAc）2催化剂和Ag 2 CO 3氧化剂，在末端甲基以及烷基链的内部苄基位置处进行C（sp 3）H酰胺化反应。该反应具有广泛的底物范围，即使以克为单位，也能以优异的收率获得各种β-内酰胺。在O 2下使用CuCl 2和Ag 2 CO 3但是，在二甲基亚砜中的空气会通过C（sp 2）H酰胺化选择性地生成2-吲哚酮。动力学同位素效应（KIE）的研究表明，Ç  H键活化是速率决定步骤。可以通过氧化除去5-甲氧基喹啉基。

  DOI：

  10.1002/anie.201311105

文献信息

• Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents
  作者：Oscar Mendoza、Guy Rossey、Léon Ghosez

  DOI：10.1016/j.tetlet.2010.03.030

  日期：2010.5

  Trialkylsilyl triflimides generated in situ are unique catalysts for the electrophilic benzylation or allylation of trialkylsilylenol ethers or allyl trialkylsilanes with non-genotoxic alkylating reagents such as benzyl and allyl acetates. In most cases the reactions are fast at room temperature and yields are high. The reaction works particularly well with electron-rich benzyl donors including derivatives

  原位生成的三烷基甲硅烷基三氟甲酸酯是独特的催化剂，用于三烷基甲硅烷基醚或烯丙基三烷基硅烷与非遗传毒性烷基化试剂（如乙酸苄基酯和乙酸烯丙酯）的亲电苄基化或烯丙基化。在大多数情况下，该反应在室温下反应很快，并且产率很高。该反应特别适用于富电子的苄基供体，包括吡咯，吲哚和呋喃的衍生物。
• Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp3) H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams
  作者：Danni Zhou、Chunxia Wang、Mingliang Li、Zheng Long、Jingbo Lan

  DOI：10.1016/j.cclet.2017.06.007

  日期：2018.1

  The direct Pd-catalyzed beta-C(sp(3))-H activation and cyclization of aliphatic amides bearing a removable 2-pyridylmethyl directing group with gem-dibromoolefins is described for the first time to construct a variety of gamma-lactams. The resulting products with Z- and E-configurations can be easily separated and purified after the reaction, demonstrating the effectiveness and applicability of the method herein developed. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• β-Arylation of Carboxamides via Iron-Catalyzed C(sp³)–H Bond Activation
  作者：Rui Shang、Laurean Ilies、Arimasa Matsumoto、Eiichi Nakamura

  DOI：10.1021/ja402806f

  日期：2013.4.24

  A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the beta-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 degrees C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.
• Copper-Catalyzed Intramolecular C(sp³)H and C(sp²)H Amidation by Oxidative Cyclization
  作者：Zhen Wang、Jizhi Ni、Yoichiro Kuninobu、Motomu Kanai

  DOI：10.1002/anie.201311105

  日期：2014.3.24

  The first copper‐catalyzed intramolecular C(sp3)H and C(sp2)H oxidative amidation has been developed. Using a Cu(OAc)2 catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp3)H amidation proceeded at a terminal methyl group, as well as at the internal benzylic position of an alkyl chain. This reaction has a broad substrate scope, and various β‐lactams were obtained in excellent yield, even

  第一铜催化的分子内C（SP 3） H和（SPç 2） ħ氧化酰胺化得到了发展。在二氯乙烷溶剂中使用Cu（OAc）2催化剂和Ag 2 CO 3氧化剂，在末端甲基以及烷基链的内部苄基位置处进行C（sp 3）H酰胺化反应。该反应具有广泛的底物范围，即使以克为单位，也能以优异的收率获得各种β-内酰胺。在O 2下使用CuCl 2和Ag 2 CO 3但是，在二甲基亚砜中的空气会通过C（sp 2）H酰胺化选择性地生成2-吲哚酮。动力学同位素效应（KIE）的研究表明，Ç  H键活化是速率决定步骤。可以通过氧化除去5-甲氧基喹啉基。