methyl (2S)-2-[(4-methoxyphenylmethyl)-(4-butyn-1-yl)amino]-3-butenoate | 1259286-16-2

• 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: methyl (2S)-2-[(4-methoxyphenylmethyl)-(4-butyn-1-yl)amino]-3-butenoate
• 英文别名: methyl (2S)-2-[but-2-ynyl-[(4-methoxyphenyl)methyl]amino]but-3-enoate
• CAS: 1259286-16-2
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: LOGDWXVWFWYOSH-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-蛋氨酸甲酯盐酸盐 在 sodium periodate 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 均三甲苯 为溶剂， 反应 72.5h， 生成 methyl (2S)-2-[(4-methoxyphenylmethyl)-(4-butyn-1-yl)amino]-3-butenoate
  参考文献：
  名称：

  Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy

  摘要：

  Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.

  DOI：

  10.1021/jo101790z

文献信息

• Stereocontrolled Total Syntheses of Isodomoic Acids G and H via a Unified Strategy
  作者：Scott E. Denmark、Jack Hung-Chang Liu、Joseck M. Muhuhi

  DOI：10.1021/jo101790z

  日期：2011.1.7

  Marine neuroexcitatory compounds isodomoic acids G and H were efficiently synthesized from a common intermediate using a silicon-based cross-coupling reaction. Dividing each target compound into the core fragment and the side-chain fragment enabled the synthesis to be convergent. The trans-2,3-disubstituted pyrrolidine core fragment was accessed through a diastereoselective rhodium-catalyzed carbonylative silylcarbocyclization reaction of a vinylglycine-derived 1,6-enyne. A stereochemically divergent desilylative iodination reaction was developed to convert the cyclization product to both E- and Z-alkenyl iodides, which would eventually lead to isodomoic acid G and isodomoic acid H, respectively. The late-stage alkenyl alkenyl silicon-based cross-coupling reaction uniting the core alkenyl iodides and the side-chain alkenylsilanol was achieved under mild conditions. Finally, two mild deprotections afforded the target molecules.