(1R,5S)-2,8,8-trimethylbicyclo<3.2.1>oct-2-en-7-one | 110415-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5S)-2,8,8-trimethylbicyclo<3.2.1>oct-2-en-7-one
• 英文别名: (1S,5S)-4,8,8-trimethylbicyclo[3.2.1]oct-3-en-6-one
• CAS: 110415-92-4
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: GQJWHWVNEJBEPZ-WCBMZHEXSA-N

物化性质

• 沸点：
  229.7±9.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,5S)-2,8,8-trimethylbicyclo<3.2.1>oct-2-en-7-one 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 (1S,5R)-6,6,8-trimethyl-2-oxabicyclo<3.3.1>non-7-en-3-one
  参考文献：
  名称：

  An Approach towards Enantiomerically Pure Taxoidic A,B-Ring Fragments

  摘要：

  DOI：

  10.1055/s-1999-6057
• 作为产物：
  描述：

  (-)-α-蒎烯 、 alkaline earth salt of/the/ methylsulfuric acid 反应 53.0h， 生成 (1R,5S)-2,8,8-trimethylbicyclo<3.2.1>oct-2-en-7-one 、 (1S,5S)-2,4,4-trimethylbicyclo<3.2.1>oct-2-en-7-one
  参考文献：
  名称：

  The Octant Rule. 21. Circular dichroism dependence on .alpha.-methyl configuration in cyclohexanones. Experiments and RPA calculations

  摘要：

  DOI：

  10.1021/ja00255a005

文献信息

• The Octant Rule. 21. Circular dichroism dependence on .alpha.-methyl configuration in cyclohexanones. Experiments and RPA calculations
  作者：David A. Lightner、Thomas D. Bouman、B. Vincent Crist、Stephen L. Rodgers、Michael A. Knobeloch、Aaron M. Jones

  DOI：10.1021/ja00255a005

  日期：1987.10
• Synthetic use of a σ-alkyl-π-allyl iron complex obtained by stereospecific ring opening of α-pinene
  作者：Titus A. Jenny、Liqian Ma

  DOI：10.1016/0040-4039(91)80763-v

  日期：1991.10

  Insertion of iron carbonyl into the four-membered ring of alpha-pinene produces a versatile iron complex exhibiting an iron-carbon sigma-bond. Reaction of this complex with various reagents, i.e. dimethyl butynedioate, produces the bicyclic ketones 2, 7, and 8 with moderate to high regioselectivity and full conservation of the optical purity of the starting terpene.
• Stereoselective Nazarov Cyclizations of Bridged Bicyclic Dienones
  作者：Robert D. Mazzola、Timothy D. White、Heidi R. Vollmer-Snarr、F. G. West

  DOI：10.1021/ol051169q

  日期：2005.6.1

  Bridged bicyclic dienones underwent silyl-directed Nazarov cyclization with generally very high diastereoselectivity. In most cases, a strong preference for cyclization to the product with an exo-disposed cyclopentenone was seen. However, the presence of additional unsaturation in the three-carbon bridge of a bicyclo[3.2.1]octadiene system caused complete reversal in selectivity with exclusive formation of the endocyclopentenone. The observed selectivities are believed to result from a combination of steric and electronic effects.
• An Approach towards Enantiomerically Pure Taxoidic A,B-Ring Fragments
  作者：Marion Wenz

  DOI：10.1055/s-1999-6057

  日期：1999.4