(6,8-dichloro-2-phenyl-2H-chromen-3-yl)methyl 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate | 1228538-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: (6,8-dichloro-2-phenyl-2H-chromen-3-yl)methyl 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate
• CAS: 1228538-84-8
• 化学式: C₂₆H₂₆Cl₂N₂O₄S
• 分子量: 533.475
• InChiKey: YJMGARIHAMYKFG-ANJPWDGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (6,8-dichloro-2-phenyl-2H-chromen-3-yl)methanol 、 D-生物素 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (6,8-dichloro-2-phenyl-2H-chromen-3-yl)methyl 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate
  参考文献：
  名称：

  Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using l-pipecolinic acid and substituted guanidine organocatalysts

  摘要：

  Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.143

文献信息

• Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using l-pipecolinic acid and substituted guanidine organocatalysts
  作者：Bhaskar C. Das、Seetaram Mohapatra、Philip D. Campbell、Sabita Nayak、Sakkarapalayam M. Mahalingam、Todd Evans

  DOI：10.1016/j.tetlet.2010.02.143

  日期：2010.5

  Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets. (C) 2010 Elsevier Ltd. All rights reserved.