[(1R,2S,3R,6R,7S)-6-methyl-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl] acetate | 182210-92-0

• 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: [(1R,2S,3R,6R,7S)-6-methyl-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl] acetate
• CAS: 182210-92-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: HKCPOLNKSWRTDZ-PORUNHMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 [(1R,2S,3R,6R,7S)-6-methyl-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl] acetate 在 氯化亚砜 作用下， 反应 0.5h， 以97%的产率得到(1S,2R,5S,6S,7R)-5-Methoxy-2-methyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0^2,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity

  摘要：

  Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.

  DOI：

  10.1021/jo9610220
• 作为产物：
  描述：

  柠康酸酐 、 环戊二烯 生成 5(RS)-hydroxy-2(SR)-methyl-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one 、 5(R)-hydroxy-2(S)-methyl-4-oxa-endo-tricyclo<5.2.1.0^2,6>dec-8-en-3-one 、 [(1R,2S,3R,6R,7S)-6-methyl-5-oxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-yl] acetate 、
  参考文献：
  名称：

  Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-endo-tricyclo[5.2.1.0^2,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity

  摘要：

  Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.

  DOI：

  10.1021/jo9610220

文献信息

• Enzymatic Kinetic Resolution of 5-Hydroxy-4-oxa-<i>endo-</i>tricyclo[5.2.1.0^2,6]dec-8-en-3-ones:  A Useful Approach to D-Ring Synthons for Strigol Analogues with Remarkable Stereoselectivity
  作者：Jan Willem J. F. Thuring、Gerard H. L. Nefkens、Margreth A. Wegman、Antonius J. H. Klunder、Binne Zwanenburg

  DOI：10.1021/jo9610220

  日期：1996.1.1

  Racemic 5-hydroxy-4-oxa-endo-tricyclo[5.2.1.0(2,6)]dec-8-en-3-one its 2-methyl analogue were resolved employing a lipase-catalyzed acetylation reaction. The latter compound thus gave access to a homochiral D-ring synthon for strigolactones. The enzymatic acetylation reaction occurred with a remarkable inversion of configuration at C-5, through which it is possible to achieve a highly efficient asymmetric synthesis of 5-acetoxy-2(5H)-furanone.