(2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester | 169774-63-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3R)-1-benzoyl-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-4-(trifluoromethylsulfonyloxy)-2,3-dihydropyrrole-2-carboxylate
• CAS: 169774-63-4
• 化学式: C₂₀H₂₂F₃NO₈S
• 分子量: 493.458
• InChiKey: LBAQXYZPPZNKSQ-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  三甲基(苯基)锡 、 (2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三(2-呋喃基)膦 、 zinc(II) chloride 作用下， 生成 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-phenyl-<4,5>-dehydropyrrolidine
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯盐酸盐 在 N,N-二甲基丙烯基脲 、 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 乙腈 、 苯 为溶剂， 反应 48.5h， 生成 (2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7

文献信息

• A biomimetic approach to the pyridone rings of the acromelic acids: A concise synthesis of acromelic acid A and an approach to acromelic acid B
  作者：Jack E. Baldwin、Andrew M. Fryer、Gareth J. Pritchard、Mark R. Spyvee、Roger C. Whitehead、Mark E. Wood

  DOI：10.1016/s0040-4020(98)00377-9

  日期：1998.6

  The syntheses of acromelic acid A 1, allo-acromelic acid A 19 and an approach towards acromelic acid B 2 are described. Palladium (0) catalysed cross-coupling reactions were used to generate C-4 catechol precursors and formation of the pyridone rings was investigated using a biomimetic oxidative cleavage - recyclisation strategy.

  描述了丙烯醛酸A 1，别甲丙酸A 19的合成和制备丙烯醛酸B 2的方法。钯（0）催化的交叉偶联反应用于生成C-4邻苯二酚前体，并使用仿生氧化裂解-循环化策略研究了吡啶酮环的形成。
• Concise syntheses of acromelic acid A and allo-acromelic acid A
  作者：Jack E. Baldwin、Andrew M. Fryer、Gareth J. Pritchard、Mark R. Spyvee、Roger C. Whitehead、Mark.E. Wood

  DOI：10.1016/s0040-4039(97)10641-4

  日期：1998.2

  Acromelic acid A 1 and allo-acromelic acid A 12 were synthesised in a biomimetic fashion. An oxidative cleavage - recyclisation strategy was used to construct the requisite C-4 pyridone from an intermediate catechol.

  毒蕈氨酸甲1和异体-acromelic酸A 12在仿生方式合成。氧化裂解-再循环策略用于从中间体邻苯二酚构建必需的C-4吡啶酮。
• A Versatile Approach to Acromelic Acid Analogues
  作者：J Baldwin

  DOI：10.1016/00404-0399(50)0841y-

  日期：1995.7.3