2a(S)5a(S)6(R)-3,4-diaza-6-menthyloxy-1-oxa-2-oxo-bicyclo<3.3.0>oct-3-ene | 120263-00-5

• 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: 2a(S)5a(S)6(R)-3,4-diaza-6-menthyloxy-1-oxa-2-oxo-bicyclo<3.3.0>oct-3-ene
• 英文别名: (3aR,4R,6aS)‐4‐(((1R,2S,5R)‐2‐isopropyl‐5‐methylcyclohexyl)oxy)‐3,3a,4,6a‐tetrahydro‐6H-furo[3,4‐c]pyrazol‐6‐one；(3aR,4R,6aS)-4-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3,3a,4,6a-tetrahydrofuro[3,4-c]pyrazol-6-one
• CAS: 120263-00-5
• 化学式: C₁₅H₂₄N₂O₃
• 分子量: 280.367
• InChiKey: PKVZFCZLWRKQIM-PVZBEVCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.25
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2a(S)5a(S)6(R)-3,4-diaza-6-menthyloxy-1-oxa-2-oxo-bicyclo<3.3.0>oct-3-ene 以 甲苯 为溶剂， 反应 12.0h， 以100%的产率得到(5R)-4-甲基-5-[[(1R,2S,5R)-5-甲基-2-(1-甲基乙基)环己基]氧基]-2-(5H)-呋喃酮
  参考文献：
  名称：

  Asymmetric 1,3-dipolar cycloadditions to 5-(R)-menthyloxy-2(5H)-furanone

  摘要：

  Various diazo compounds, nitrile oxides, nitrones and azomethine ylides were examined in 1,3-dipolar cycloadditions to enantiomerically pure 5-(R)-menthyloxy-2(5H)-furanone 1a. Pyrazoline 9 was obtained in 100% c.y. as a mixture of 2 diastereoisomers in ratios up to 72 : 28, whereas pyrazoline 16 was obtained in 100% c.y. as a single enantiomer. Photochemically pyrazolines 9 and 10 have been converted to cyclopropanes 11 and 13. Under thermal conditions pyrazoline 9 is converted to 4-methyl-5-menthyloxy-2(5H)-furanone. Isoxazoles 21a-24a were obtained enantiomerically pure via nitrile oxide addition to la in 64-67% yield. Nitrone addition afforded isoxazolidines 27, 28 and 34 with complete anti-facial- and regiochemistry, but with endo-exo selectivities up to 76%. Enantiomerically pure isoxazolidines were obtained in 25-75% yield. Pyrrolidine 36 was obtained diastereomerically pure in 81% c.y. Pyrrolidines 42 and 45, however, were obtained as diastereomeric mixtures in 37% resp. 6% yield.

  DOI：

  10.1016/0957-4166(94)80023-5
• 作为产物：
  描述：

  重氮甲烷 、 (5R)-(L-menthyloxy)-2(5H)-furanone 以 乙醚 为溶剂， 反应 48.0h， 以48%的产率得到2a(S)5a(S)6(R)-3,4-diaza-6-menthyloxy-1-oxa-2-oxo-bicyclo<3.3.0>oct-3-ene
  参考文献：
  名称：

  2-氨基甲基-1-环丙烷羧酸的四种立体异构体：合成和生物学评价

  摘要：

  在这里，我们报告了一种不对称合成环丙烷融合 GABA 类似物的实用方法。以 2-糠醛为原料，经过 10 步合成顺式异构体 (CAMP)；(−)- 和 (+)-CAMP·H...

  DOI：

  10.1246/bcsj.20190168

文献信息

• Asymmetric 1,3-dipolar cycloadditions to 5-menthyloxy-2[5H]-furanones.
  作者：Ben de Lange、Ben L. Feringa

  DOI：10.1016/s0040-4039(00)80747-9

  日期：1988.1
• FERINGA, BEN L.;DE, LANGE BEN;DE, JONG JOHANNES C., J. ORG. CHEM., 54,(1989) N0, C. 2471-2475
  作者：FERINGA, BEN L.、DE, LANGE BEN、DE, JONG JOHANNES C.

  DOI：——

  日期：——
• DE, LANGE BEN;FERINGA, BEN L., TETRAHEDRON LETT., 29,(1988) N 41, C. 5317-5320
  作者：DE, LANGE BEN、FERINGA, BEN L.

  DOI：——

  日期：——