methyl 2-(4-methoxybenzamido)-4-phenylbutanoate | 1332649-06-5

• 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-methoxybenzamido)-4-phenylbutanoate
• 英文别名: Methyl 2-[(4-methoxybenzoyl)amino]-4-phenylbutanoate；methyl 2-[(4-methoxybenzoyl)amino]-4-phenylbutanoate
• CAS: 1332649-06-5
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: CPVAVYOJRSGAEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-methoxybenzamido)-4-phenylbutanoate 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-(4-methoxyphenyl)-4-phenethyloxazol-5(4H)-one
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524
• 作为产物：
  描述：

  2-(p-methoxyphenyl)-5-methoxyoxazole 在 copper diacetate 、 palladium diacetate 、 乙酰氯 作用下， 以 甲醇 、 乙腈 为溶剂， 60.0 ℃ 、344.75 kPa 条件下， 反应 18.0h， 生成 methyl 2-(4-methoxybenzamido)-4-phenylbutanoate
  参考文献：
  名称：

  通过C–H键激活Pd催化的恶唑C4烯烃加成反应：功能化氨基醇和氨基酸衍生物的不同合成

  摘要：

  在温和的条件下，通过C–H键的活化，实现了Pd催化的恶唑的C4烯化反应。在一系列底物上显示该反应是普遍的。还建立了用于这些产物的发散转化以提供官能化的氨基醇和氨基酸衍生物的新方案。

  DOI：

  10.1021/ol201865h

文献信息

• Efficient synthesis of oxazoles by dirhodium(ii)-catalyzed reactions of styryl diazoacetate with oximes
  作者：Xinfang Xu、Peter Y. Zavalij、Wenhao Hu、Michael P. Doyle

  DOI：10.1039/c2cc36537e

  日期：——

  An efficient one-step synthesis of multi-functionalized oxazole derivatives is achieved in high yield by dirhodium(II)-catalyzed reactions of styryl diazoacetate with aryl oximes.

  通过二铑(II)催化苯乙烯基重氮乙酸酯与芳基肟的反应，以高产率高效一步合成多官能化恶唑衍生物。
• Pd-Catalyzed C4-Olefination of Oxazoles via C–H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives
  作者：Sunliang Cui、Lukasz Wojtas、Jon C. Antilla

  DOI：10.1021/ol201865h

  日期：2011.10.7

  A Pd-catalyzed C4-olefination of oxazoles via C–H bond activation under mild conditions was achieved. The reaction was shown to be general over a range of substrates. New protocols for the divergent transformation of these products to provide functionalized amino alcohol and amino acid derivatives have also been established.

  在温和的条件下，通过C–H键的活化，实现了Pd催化的恶唑的C4烯化反应。在一系列底物上显示该反应是普遍的。还建立了用于这些产物的发散转化以提供官能化的氨基醇和氨基酸衍生物的新方案。
• Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and <i>N</i>,<i>O</i>-Acetal Derivatives
  作者：Tianli Wang、Zhaoyuan Yu、Ding Long Hoon、Claire Yan Phee、Yu Lan、Yixin Lu

  DOI：10.1021/jacs.5b10524

  日期：2016.1.13

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.