ethyl 2-(1-hydroxy-4-methyl-3-oxopentyl)thiazole-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(1-hydroxy-4-methyl-3-oxopentyl)thiazole-4-carboxylate
• 英文别名: ethyl 2-[(1R)-1-hydroxy-4-methyl-3-oxopentyl]-1,3-thiazole-4-carboxylate
• 化学式: C₁₂H₁₇NO₄S
• 分子量: 271.337
• InChiKey: AGJQQIXQKJERBP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-hydroxy-4-methyl-3-oxopentyl)thiazole-4-carboxylate 、 苄胺 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成
  参考文献：
  名称：

  噻唑-甲醛的不对称醛醇缩合反应：图布伐林类似物的区域和立体选择性合成

  摘要：

  AbstractThe first organocatalytic enantioselective approach to precursors of tubuvaline (pre‐Tuv) is presented employing a prolinamide‐catalyzed aldol reaction of easily accessible thiazole‐carbaldehyde with methyl isopropyl ketone “on water” in excellent yield as well as regio‐ and enantioselectivities. The analogues of pre‐Tuv were achieved using an L‐proline‐catalyzed direct asymmetric aldol reaction of substituted thiazole‐carbaldehydes with acetone. A direct and flexible approach to the tubavaline (Tuv) core of tubusylins has been established employing the reductive amination of the pre‐Tuv species. The key aldol reaction should greatly expand the potential of this strategy to the synthesis of natural product tubulysins and a range of analogues.magnified image

  DOI：

  10.1002/adsc.201400640
• 作为产物：
  描述：

  2-甲基噻唑-4-甲酸乙酯 在 selenium(IV) oxide 、 甲酸 、 2,4,6-三氟苯甲酸 、 C₁₉H₁₉N₅O 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 132.5h， 生成 ethyl 2-(1-hydroxy-4-methyl-3-oxopentyl)thiazole-4-carboxylate
  参考文献：
  名称：

  噻唑-甲醛的不对称醛醇缩合反应：图布伐林类似物的区域和立体选择性合成

  摘要：

  AbstractThe first organocatalytic enantioselective approach to precursors of tubuvaline (pre‐Tuv) is presented employing a prolinamide‐catalyzed aldol reaction of easily accessible thiazole‐carbaldehyde with methyl isopropyl ketone “on water” in excellent yield as well as regio‐ and enantioselectivities. The analogues of pre‐Tuv were achieved using an L‐proline‐catalyzed direct asymmetric aldol reaction of substituted thiazole‐carbaldehydes with acetone. A direct and flexible approach to the tubavaline (Tuv) core of tubusylins has been established employing the reductive amination of the pre‐Tuv species. The key aldol reaction should greatly expand the potential of this strategy to the synthesis of natural product tubulysins and a range of analogues.magnified image

  DOI：

  10.1002/adsc.201400640