(1R,2R,4R)-2-exo-hydroxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane | 620621-14-9

• 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: (1R,2R,4R)-2-exo-hydroxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane
• 英文别名: (1R,2R,4R)-2-(Furan-2-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol；(1R,2R,4R)-2-(furan-2-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 620621-14-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: RCKZRMRIWTXHKX-HONMWMINSA-N

物化性质

• 沸点：
  300.4±17.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R)-2-exo-hydroxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane 在 amberlyst-15 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到(1R,2R,4R)-2-exo-hydroperoxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Time Dependent Density Functional Response Theory Calculation of Optical Rotation as a Method for the Assignment of Absolute Configuration of Camphor-Derived Furyl Hydroperoxide and Alcohol

  摘要：

  The absolute configuration of (R)-(+)-camphor-derived furyl hydroperoxide and alcohol, which exhibit a number of stable conformations, has been successfully accomplished on the basis of time dependent density functional response theory (TDDFT) calculations of optical rotation. Assuming standard approximations, it has been found that the results are improved by using populations for the conformers derived from free energy differences instead of the commonly used PES minimum differences. This represents the first computational study devoted to the direct determination of absolute configuration of an optically pure hydroperoxide, without any need of its further chemical derivatization.

  DOI：

  10.1021/jp047053d
• 作为产物：
  描述：

  (1R,2S,4R)-2-endo-hydroxy-2-exo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane 在 双氧水 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 28.5h， 生成 (1R,2R,4R)-2-exo-hydroxy-2-endo-(2'-furyl)-1,7,7-trimethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  Renewable camphor-derived hydroperoxide: synthesis and use in the asymmetric epoxidation of allylic alcoholsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b303904h/

  摘要：

  可再生对映体纯叔呋喃基氢过氧化物可以从低成本 (+)-(1R)-樟脑开始，通过两步轻松合成，并已用于烯丙醇的不对称环氧化和动力学拆分（对映选择性高达 46%）。

  DOI：

  10.1039/b303904h

文献信息

• Renewable camphor-derived hydroperoxide: synthesis and use in the asymmetric epoxidation of allylic alcoholsElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b3/b303904h/
  作者：Alessandra Lattanzi、Patrizia Iannece、Assunta Vicinanza、Arrigo Scettri

  DOI：10.1039/b303904h

  日期：——

  Renewable enantiopure tertiary furyl hydroperoxide has been easily synthesized in two steps starting from low cost (+)-(1R)-camphor and it has been used in the asymmetric epoxidation and kinetic resolution of allylic alcohols (enantioselectivities up to 46%).

  可再生对映体纯叔呋喃基氢过氧化物可以从低成本 (+)-(1R)-樟脑开始，通过两步轻松合成，并已用于烯丙醇的不对称环氧化和动力学拆分（对映选择性高达 46%）。
• Time Dependent Density Functional Response Theory Calculation of Optical Rotation as a Method for the Assignment of Absolute Configuration of Camphor-Derived Furyl Hydroperoxide and Alcohol
  作者：Alessandra Lattanzi、Rosario G. Viglione、Arrigo Scettri、Riccardo Zanasi

  DOI：10.1021/jp047053d

  日期：2004.12.1

  The absolute configuration of (R)-(+)-camphor-derived furyl hydroperoxide and alcohol, which exhibit a number of stable conformations, has been successfully accomplished on the basis of time dependent density functional response theory (TDDFT) calculations of optical rotation. Assuming standard approximations, it has been found that the results are improved by using populations for the conformers derived from free energy differences instead of the commonly used PES minimum differences. This represents the first computational study devoted to the direct determination of absolute configuration of an optically pure hydroperoxide, without any need of its further chemical derivatization.