(+)-menthyl (Z)-2-benzoylamino-3-hydroxyacrylate

• 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: (+)-menthyl (Z)-2-benzoylamino-3-hydroxyacrylate
• 英文别名: [(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (Z)-2-benzamido-3-hydroxyprop-2-enoate
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: IUNFKHKGLBVSLW-IDTPUJOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 (+)-menthyl (Z)-2-benzoylamino-3-hydroxyacrylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到(+)-menthyl (Z)-2-benzoylamino-3-ethoxycarbonyloxyacrylate
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

  摘要：

  The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates. (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective synthesis of the exo/endo compounds 5c,d and 5 'c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)(2) as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

  DOI：

  10.1021/jo010374q
• 作为产物：
  描述：

  D-薄荷醇 、 4-hydroxymethylene-2-phenyl-2-oxazolin-5-one 在 双(二丁基氯基锡(四))氧化物 作用下， 以 苯 为溶剂， 反应 24.0h， 以85%的产率得到(+)-menthyl (Z)-2-benzoylamino-3-hydroxyacrylate
  参考文献：
  名称：

  Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives

  摘要：

  The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates. (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective synthesis of the exo/endo compounds 5c,d and 5 'c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)(2) as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.

  DOI：

  10.1021/jo010374q

文献信息

• Asymmetric Synthesis of 2-Amino-3-hydroxynorbornene-2-carboxylic Acid Derivatives
  作者：Giorgio Abbiati、Francesca Clerici、Maria Luisa Gelmi、Andrea Gambini、Tullio Pilati

  DOI：10.1021/jo010374q

  日期：2001.9.1

  The enantioselective synthesis of 2-amino-3-hydroxynorbornene-2-carboxylic acid derivatives (5) was studied using the Diels-Alder reaction between cyclopentadiene and different dienophiles, i.e., alkyl 5-oxo-2-phenyloxazol-4-methylenecarbonates (1) or 2-benzoylamino-3-alkoxycarbonyloxy-acrylates. (12), operating with different Lewis acids and both with thermal and with ultrasound conditions. The enantioselective synthesis of the exo/endo compounds 5c,d and 5 'c,d was achieved starting from the chiral menthyl acrylates 12b,c using Mg(ClO4)(2) as the catalyst and ultrasound. The cycloadducts were obtained in very good yield, in mild conditions, in short time, and in good diastereomeric excess (exo, 80%; endo, 87%). Finally, the use of alkylidene-oxazolones or acrylates and EtAlCl2 or Mg(ClO4)(2) as the catalyst allowed control of the cycloaddition reaction in favor of the exo or endo products.