methyl (2S)-2-[[(4-methoxyphenyl)methyl]-(2-butyn-1-yl)-amino]-4-(methylsulfinyl)butanoate | 1259286-15-1

• 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-methoxyphenyl)methyl]-(2-butyn-1-yl)-amino]-4-(methylsulfinyl)butanoate
• 英文别名: methyl (2S)-2-[but-2-ynyl-[(4-methoxyphenyl)methyl]amino]-4-methylsulfinylbutanoate
• CAS: 1259286-15-1
• 化学式: C₁₈H₂₅NO₄S
• 分子量: 351.467
• InChiKey: DSROGZPZQNFZRW-KEJDIYNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(4-methoxyphenyl)methyl]-(2-butyn-1-yl)-amino]-4-(methylsulfinyl)butanoate 在 三苯基膦 作用下， 以 均三甲苯 为溶剂， 反应 27.0h， 以74%的产率得到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
• 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 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.5h， 生成 methyl (2S)-2-[[(4-methoxyphenyl)methyl]-(2-butyn-1-yl)-amino]-4-(methylsulfinyl)butanoate
  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