1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-(furan-2-yl)ethanone | 445399-66-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-(furan-2-yl)ethanone
• 英文别名: 1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-(furan-2-yl)ethanone
• CAS: 445399-66-6
• 化学式: C₁₆H₂₁NO₄S
• 分子量: 323.413
• InChiKey: XIBXWRNQBHJEAL-AXAPSJFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-(furan-2-yl)ethanone 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2S)-2-(furan-2-yl)propan-1-ol
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol

  摘要：

  The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00023-x
• 作为产物：
  描述：

  2-呋喃乙酰氯 、 (2R)-bornane-10,2-sultam 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以76%的产率得到1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-(furan-2-yl)ethanone
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol

  摘要：

  The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00023-x

文献信息

• Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol
  作者：Anja Bierstedt、Jörn Stölting、Roland Fröhlich、Peter Metz

  DOI：10.1016/s0957-4166(02)00023-x

  日期：2002.1

  The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.