(1S)-1-[(1R,2S,3R,4S)-3-[(1R)-1-hydroxyethyl]-2-bicyclo[2.2.1]hept-5-enyl]ethanol | 202480-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-[(1R,2S,3R,4S)-3-[(1R)-1-hydroxyethyl]-2-bicyclo[2.2.1]hept-5-enyl]ethanol
• CAS: 202480-24-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: LSGIYLIJAFTOMC-MBVBQEHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.19
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(1R,2S,3R,4S)-3-[(1R)-1-hydroxyethyl]-2-bicyclo[2.2.1]hept-5-enyl]ethanol 在 碘 、 potassium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以80%的产率得到
  参考文献：
  名称：

  Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane

  摘要：

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.

  DOI：

  10.1002/jccs.199700094
• 作为产物：
  描述：

  endo-2,3-diacetylbicyclo[2.2.1]hept-5-ene 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到(1S)-1-[(1R,2S,3R,4S)-3-[(1R)-1-hydroxyethyl]-2-bicyclo[2.2.1]hept-5-enyl]ethanol
  参考文献：
  名称：

  Synthesis of 3,11-Dioxatetracyclo[6.3.0.0^2,6.0^5,9]undecanes and 3,5,7-Trioxapentacyclo[7.2.1.0^2,8.0^4,11.0^6,10]dodecane

  摘要：

  AbstractThe synthesis of 3,11‐dioxatetracyclo[6.3.0.02,6.05,9]undecanes has been accomplished from furans in a short sequence by iodine‐induced cyclization reaction. The application of iodine‐induced cyclization reaction for the synthesis of 3,5,7‐trioxapentacyclo[7.2.1.02,8.04,11.06,10]dodecane itself was also demonstrated.

  DOI：

  10.1002/jccs.199700094

文献信息

• Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group
  作者：Hsien-Jen Wu、Ching-Shiun Chao、Chu-Chung Lin

  DOI：10.1021/jo980632s

  日期：1998.10.1

  The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2Cl2 at -78 degrees C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.