methyl 3-hydroxy-2-(pent-4-enamido)propanoate

• 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 3-hydroxy-2-(pent-4-enamido)propanoate
• 英文别名: Methyl 3-hydroxy-2-(pent-4-enoylamino)propanoate
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: OIKKWEMALUANLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  methyl 3-hydroxy-2-(pent-4-enamido)propanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 chromium dichloride 、 (IMes)AuNTf₂ 、 三氯溴甲烷 、 二乙胺基三氟化硫 、 C₂₄H₄₂BCl 、 四丁基氟化铵 、 水 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二甲基甲酰胺 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 15.08h， 生成 2'-((S,3E,6Z,9E)-6,8-dimethylundeca-3,6,9-trien-1-yl)-4-((R)-1-methoxy-2-((2R,4R,6R)-6-methoxy-4-((4-methoxybenzyl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)ethyl)-2,4'-bioxazole
  参考文献：
  名称：

  Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods

  摘要：

  A new total synthesis of (-)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.

  DOI：

  10.1055/s-0032-1318109
• 作为产物：
  描述：

  4-戊烯酸 、 DL-丝氨酸甲酯盐酸盐 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 乙腈 为溶剂， 以89%的产率得到methyl 3-hydroxy-2-(pent-4-enamido)propanoate
  参考文献：
  名称：

  Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods

  摘要：

  A new total synthesis of (-)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.

  DOI：

  10.1055/s-0032-1318109

文献信息

• Synthesis of (-)-Hennoxazole A: Integrating Batch and Flow Chemistry Methods
  作者：Steven Ley、Amadeo Fernández、Zebulon Levine、Marcus Baumann、Sarah Sulzer-Mossé、Christof Sparr、Sabrina Schläger、Albrecht Metzger、Ian Baxendale

  DOI：10.1055/s-0032-1318109

  日期：——

  A new total synthesis of (-)-hennoxazole A is reported. The synthetic approach is based on the preparation of three similarly sized fragments resulting in a fast and convergent assembly of the natural product. The three key reactions of the synthesis include a highly stereoselective 1,5-anti aldol coupling, a gold-catalyzed alkoxycyclization reaction, and a stereocontrolled diene cross-metathesis. The synthesis involves integrated batch and flow chemistry methods leading to the natural product in 16 steps longest linear sequence and 2.8% overall yield.