<3R-<3α(1R,2S,5R),3aα,4α,7α,7aα>>-3a,4,7,7a-tetrahydro-3-<<5-methyl-2-(1-methyl-ethyl)-cyclohexyl>oxy>-4,7-methanoisobenzofuran-1(3H)-one | 72937-74-7

• 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: <3R-<3α(1R,2S,5R),3aα,4α,7α,7aα>>-3a,4,7,7a-tetrahydro-3-<<5-methyl-2-(1-methyl-ethyl)-cyclohexyl>oxy>-4,7-methanoisobenzofuran-1(3H)-one
• 英文别名: (1R,2S,5R,6R,7S)-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-4-oxatricyclo[5.2.1.02,6]dec-8-en-3-one
• CAS: 72937-74-7
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: YAMJFZHNMNGZSI-AJFMGFNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  <3R-<3α(1R,2S,5R),3aα,4α,7α,7aα>>-3a,4,7,7a-tetrahydro-3-<<5-methyl-2-(1-methyl-ethyl)-cyclohexyl>oxy>-4,7-methanoisobenzofuran-1(3H)-one 在 水 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 生成 3-hydroxy-3a,4,7,7a-tetrahydro-4,5-methano-(3H)-isobenzofuran-1-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with 5-menthyloxy-2-(5H)-furanone

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)80024-5
• 作为产物：
  描述：

  (1R,2R,5R,6S,7S)-5-Ethoxy-2-(toluene-4-sulfinyl)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 在 samarium diiodide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 苯 为溶剂， 生成 <3R-<3α(1R,2S,5R),3aα,4α,7α,7aα>>-3a,4,7,7a-tetrahydro-3-<<5-methyl-2-(1-methyl-ethyl)-cyclohexyl>oxy>-4,7-methanoisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of γ-alkoxy-α-sulfinylbutenolides

  摘要：

  The synthesis of the enantiomerically pure 5-ethoxy-3-p-tolylsulfinyl-2(5H)-furanones (2a and 2b) and the study of their behaviour as dienophiles in asymmetric Diels-Alder reactions with cyclopentadiene arc reported. Depending on the reaction conditions, the pi-facial selectivity is mainly controlled by the sulfur or C-5 configurations.

  DOI：

  10.1016/s0957-4166(00)82331-9

文献信息

• An Alternative Enantioselective Synthesis of (+)-Tricyclodecadienone
  作者：Joop Knol、Ben L Feringa*

  DOI：10.1016/s0040-4039(97)00392-4

  日期：1997.4

  The enantiomerically pure endo-cycloadduct , obtained from the thermal Diels-Alder reaction of 5R-(l-menthyloxy)-2(5H)-furanone with cyclopentadiene is converted into (+)-tricyclo[5.2.1.0  and ]decadi-4,8-en-3-one ((+)-) in a one-pot procedure via ring-opening with lithium methyl dimethylphosphonate followed by an intramolecular Wittig-Horner-Emmons reaction in THF. The use of LiBr as additive in this

  的对映体纯内切-cycloadduct ，从5的热第尔斯-阿尔德反应获得的[R - （升-menthyloxy）-2（5H） -呋喃酮与环戊二烯转化成（+） -三环[5.2.1.0和] decadi -4-一锅法中，通过二甲基膦酸锂甲酯的开环反应，制得1，8-en-3-one（（+）- ），然后在THF中进行分子内Wittig-Horner-Emmons反应。在此步骤中使用溴化锂作为添加剂对形成镍极为有益。©1997由Elsevier Science Ltd发布。
• 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
• DE, JONG JOHANNES C.;FERINGA, BEN L., TETRAHEDRON LETT., 30,(1989) N1, C. 7239-7240
  作者：DE, JONG JOHANNES C.、FERINGA, BEN L.

  DOI：——

  日期：——
• 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 of γ-alkoxy-α-sulfinylbutenolides
  作者：J.Carlos Carretero、J.L.Garcia Ruano、A. Lorente、F. Yuste

  DOI：10.1016/s0957-4166(00)82331-9

  日期：1993.2

  The synthesis of the enantiomerically pure 5-ethoxy-3-p-tolylsulfinyl-2(5H)-furanones (2a and 2b) and the study of their behaviour as dienophiles in asymmetric Diels-Alder reactions with cyclopentadiene arc reported. Depending on the reaction conditions, the pi-facial selectivity is mainly controlled by the sulfur or C-5 configurations.