(6R)-(+)-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide | 690656-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (6R)-(+)-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide
• 英文别名: (6R)-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-5,5-dimethyl-4,6-dihydrocyclopenta[b]thiophene-6-carboxamide
• CAS: 690656-69-0
• 化学式: C₁₅H₂₃NO₂S
• 分子量: 281.419
• InChiKey: ATIUTEZBBMBRRL-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-(+)-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到(6R)-(-)-2-(5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophen-6-yl)-(4S)-4-isopropyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Cyclopenta[b]thiophene-alkyloxazolines: new nitrogen–sulfur hybrid ligands and their use in asymmetric palladium-catalyzed allylic alkylation

  摘要：

  New chiral nitrogen and sulfur containing hybrid ligands have been prepared and fully characterized. Their structure includes cyclopenta[b]tiophene and oxazoline moieties as sources of chirality. Their catalytic activity has been tested successfully in the Pd-allylic alkylation leading to enantioselectivities of up to 74% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.036
• 作为产物：
  描述：

  4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 18-冠醚-6 、 三氟化硼乙醚 、 R(+)-alpha-甲基苄胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙二醇 、 丙酮 、 甲苯 为溶剂， 反应 42.83h， 生成 (6R)-(+)-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxamide
  参考文献：
  名称：

  Cyclopenta[b]thiophene-alkyloxazolines: new nitrogen–sulfur hybrid ligands and their use in asymmetric palladium-catalyzed allylic alkylation

  摘要：

  New chiral nitrogen and sulfur containing hybrid ligands have been prepared and fully characterized. Their structure includes cyclopenta[b]tiophene and oxazoline moieties as sources of chirality. Their catalytic activity has been tested successfully in the Pd-allylic alkylation leading to enantioselectivities of up to 74% ee. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.036

文献信息

• Cyclopenta[b]thiophene-alkyloxazolines: new nitrogen–sulfur hybrid ligands and their use in asymmetric palladium-catalyzed allylic alkylation
  作者：Bianca-Flavia Bonini、Laurent Giordano、Mariafrancesca Fochi、Mauro Comes-Franchini、Luca Bernardi、Elena Capitò、Alfredo Ricci

  DOI：10.1016/j.tetasy.2004.01.036

  日期：2004.3

  New chiral nitrogen and sulfur containing hybrid ligands have been prepared and fully characterized. Their structure includes cyclopenta[b]tiophene and oxazoline moieties as sources of chirality. Their catalytic activity has been tested successfully in the Pd-allylic alkylation leading to enantioselectivities of up to 74% ee. (C) 2004 Elsevier Ltd. All rights reserved.