(1R,2S,5R)-5-Methylbicyclo<3.2.0>heptan-2-ol | 169868-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,5R)-5-Methylbicyclo<3.2.0>heptan-2-ol
• 英文别名: (1R,2S,5R)-5-methylbicyclo[3.2.0]heptan-2-ol
• CAS: 169868-19-3
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: KAJXHWRDBBLNGM-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-5-Methylbicyclo<3.2.0>heptan-2-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以69%的产率得到(+/-)5-methylbicyclo<3.2.0>heptan-2-one
  参考文献：
  名称：

  Stereoselective Intramolecular Copper(I)-Catalyzed [2 + 2]- Photocycloadditions. Enantioselective Synthesis of (+)- and (-)-Grandisol

  摘要：

  This work deals with copper(I)-catalyzed intramolecular [2 + 2]-photocycloadditions of 1,6-diene derivatives. The bridgehead carbons C-l and C-5 of the resulting bicyclo[3.2.0]heptanes are generated stereoselectively by using chiral starting material, chiral catalysts, or chiral auxiliaries. The irradiation of (S)-3 leads to enantiomerically pure 4 and 5 which opens a new synthetic route to enantiomerically pure (+)- and (-)-grandisol 9. The use of chiral copper complexes as catalysts delivers enantiomeric excesses below 5%. The reason for these small excesses is a low reactivity of the chiral copper complexes, as confirmed by CD-spectroscopic measurements. Malic acid or amino carboxylic acid derivatives as chiral auxiliaries yield the bicyclic alcohols 4 and 5 with enantiomeric excesses up to 15%. The employment of a chiral diol as an auxiliary delivers a chiral ketal 36, and the resulting ketone 7 exhibits enantiomeric excesses up to 60%.

  DOI：

  10.1021/jo00127a034
• 作为产物：
  描述：

  (+/-)5-methylbicyclo<3.2.0>heptan-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到(1R,2S,5R)-5-Methylbicyclo<3.2.0>heptan-2-ol
  参考文献：
  名称：

  2-Bicyclo[3.2.0]heptyl and 7-norbornyl cations

  摘要：

  DOI：

  10.1021/jo00222a003

文献信息

• Synthesis and solvolysis of derivatives of 7-methyl-7-hydroxynorbornane and the epimeric 7-methyl-7-hydroxynorbornenes
  作者：Paul G. Gassman、John M. Pascone

  DOI：10.1021/ja00804a042

  日期：1973.11
• Copper(I) catalysis of olefin photoreactions. 9. Photobicyclization of .alpha.-, .beta.-, and .gamma.-alkenylallyl alcohols
  作者：Robert G. Salomon、Daniel J. Coughlin、Subrata Ghosh、Michael G. Zagorski

  DOI：10.1021/ja00368a014

  日期：1982.2
• A novel C7H11+ cation
  作者：Wolfgang Kirmse、Rainer Siegfried、Joachim Streu

  DOI：10.1021/ja00320a057

  日期：1984.4
• Langer, Klaus; Mattay, Jochen; Heidbreder, Andreas, Liebigs Annalen der Chemie, 1992, # 3, p. 257 - 260
  作者：Langer, Klaus、Mattay, Jochen、Heidbreder, Andreas、Moeller, Manfred

  DOI：——

  日期：——
• KIRMSE, W.;STREU, J., J. ORG. CHEM., 1985, 50, N 22, 4187-4194
  作者：KIRMSE, W.、STREU, J.

  DOI：——

  日期：——