(+)-1,1,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]heptan-2-one | 853911-91-8

• 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: (+)-1,1,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]heptan-2-one
• 英文别名: (1R,3R,4S)-1,7,7-trimethyl-3-triethylsilyloxybicyclo[2.2.1]heptan-2-one
• CAS: 853911-91-8
• 化学式: C₁₆H₃₀O₂Si
• 分子量: 282.498
• InChiKey: VOPHOUZVNRPQLO-IOASZLSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-1,1,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]heptan-2-one 在 cerium(III) chloride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (-)-(1R,2R,3R,4S)-1,7,7-trimethyl-2-phenyl-bicyclo[2.2.1]heptane-2,3-diol
  参考文献：
  名称：

  Practical and Efficient Multigram Preparation of a Camphor-Derived Diol for the Enantioselective Lewis Acid Catalyzed Allylboration of Aldehydes

  摘要：

  Chiral diols are important molecules with widespread use as chiral auxiliaries and ligands in enantioselective synthesis. Therefore, efficient and practical syntheses of highly dissymmetrical nonracemic diols are still a meaningful pursuit. Two new routes to access camphor-derived chiral diol 1 have been developed. One route employs camphorquinone (3) as the starting material, affording in only two steps the desired diol in 55% overall yield. The second route, from camphor (2), leads to the desired diol in an efficient four-step synthesis, with an overall yield of 55%.

  DOI：

  10.1021/jo050207g
• 作为产物：
  描述：

  三乙基氯硅烷 在 Oxone 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 (+)-1,1,7-trimethyl-2-(triethylsilyloxy)bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Practical and Efficient Multigram Preparation of a Camphor-Derived Diol for the Enantioselective Lewis Acid Catalyzed Allylboration of Aldehydes

  摘要：

  Chiral diols are important molecules with widespread use as chiral auxiliaries and ligands in enantioselective synthesis. Therefore, efficient and practical syntheses of highly dissymmetrical nonracemic diols are still a meaningful pursuit. Two new routes to access camphor-derived chiral diol 1 have been developed. One route employs camphorquinone (3) as the starting material, affording in only two steps the desired diol in 55% overall yield. The second route, from camphor (2), leads to the desired diol in an efficient four-step synthesis, with an overall yield of 55%.

  DOI：

  10.1021/jo050207g

文献信息

• Practical and Efficient Multigram Preparation of a Camphor-Derived Diol for the Enantioselective Lewis Acid Catalyzed Allylboration of Aldehydes
  作者：Hugo Lachance、Miguel St-Onge、Dennis G. Hall

  DOI：10.1021/jo050207g

  日期：2005.5.1

  Chiral diols are important molecules with widespread use as chiral auxiliaries and ligands in enantioselective synthesis. Therefore, efficient and practical syntheses of highly dissymmetrical nonracemic diols are still a meaningful pursuit. Two new routes to access camphor-derived chiral diol 1 have been developed. One route employs camphorquinone (3) as the starting material, affording in only two steps the desired diol in 55% overall yield. The second route, from camphor (2), leads to the desired diol in an efficient four-step synthesis, with an overall yield of 55%.