(1R,2S,5R,6R,7S)-5-methoxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one | 113033-29-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2S,5R,6R,7S)-5-methoxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 113033-29-7
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VZYLHCHPEGGRAG-RZWYQDGFSA-N

物化性质

• 沸点：
  322.7±42.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R,6R,7S)-5-methoxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one 在 ammonium hydroxide 作用下， 反应 15.0h， 以70%的产率得到3-hydroxy-4,7-methano-1,3,3a,4,7,7a-hexahydroisoindol-1-one
  参考文献：
  名称：

  Farina, Francisco; Martin, M. Victoria; Paredes, M. Carmen, Heterocycles, 1984, vol. 22, # 8, p. 1733 - 1739

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(R)-5-methoxyfuran-2(5H)-one 、 环戊二烯 以 甲苯 为溶剂， 反应 4.5h， 生成 (1R,2S,5R,6R,7S)-5-methoxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with a chiral maleic anhydride analog, 5-(1-menthyloxy)-2(5H)-furanone

  摘要：

  DOI：

  10.1021/jo00240a048

文献信息

• Asymmetric Diels-Alder reactions with 5-menthyloxy-2-(5H)-furanone
  作者：Johannes C. de Jong、Fré van Bolhuis、Ben L. Feringa

  DOI：10.1016/s0957-4166(00)80024-5

  日期：1991.1

  A new class of chiral dienophiles, 5-alkoxy-2(5H)-furanones, has been developed. Both enantiomers of 5-menthyloxy-2(5H)-furanone are readily available in enantiomerically pure form, starting from furfural and d- or l-menthol. Excellent diastereoselectivities (d.e. greater-than-or-equal-to 99%) are obtained in thermal Diels-Alder reactions with several cyclic and acyclic dienes. The use of silyl dienol ethers has resulted in new routes to enantiomerically pure cyclohexanones in a highly regioselective manner.
• 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.
• FERINDA, BEN L.;JONG, JOHANNES C. DE, J. ORG. CHEM., 53,(1988) N 5, 1125-1127
  作者：FERINDA, BEN L.、JONG, JOHANNES C. DE

  DOI：——

  日期：——
• Asymmetric Diels-Alder reactions with a chiral maleic anhydride analog, 5-(1-menthyloxy)-2(5H)-furanone
  作者：Ben L. Feringa、Johannes C. De Jong

  DOI：10.1021/jo00240a048

  日期：1988.3
• Farina, Francisco; Martin, M. Victoria; Paredes, M. Carmen, Heterocycles, 1984, vol. 22, # 8, p. 1733 - 1739
  作者：Farina, Francisco、Martin, M. Victoria、Paredes, M. Carmen、Ortega, M. Carmen、Tito, Amelia

  DOI：——

  日期：——