(R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-pentan-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-pentan-1-ol
• 英文别名: (1R)-1-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]pentan-1-ol
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: PXXRXOLZJBHECE-OBPIAQAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-pentan-1-ol 在 二甲基硫 、 臭氧 作用下， 生成 3β-n-Butyl-2,7,12-trioxatetracyclo[6.3.1.0^4,11.0^5,9]dodecane
  参考文献：
  名称：

  Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group

  摘要：

  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.

  DOI：

  10.1021/jo980632s
• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-Pentanoyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-pentan-1-ol
  参考文献：
  名称：

  Synthesis of New Type Diacetal Trioxa-Cage Compounds via an Intramolecular Nucleophilic Addition of the Hydroxy Group to the Carbonyl Oxide Group

  摘要：

  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.

  DOI：

  10.1021/jo980632s

文献信息

• 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
  作者：Hui-Chang Lin、Chung-Yi Wu、Hsien-Jen Wu

  DOI：10.1002/jccs.199700094

  日期：1997.12

  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.
• Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers
  作者：Katsufumi Suzuki、Kohei Inomata

  DOI：10.1016/s0040-4039(02)02711-9

  日期：2003.1

  Continuous nucleophilic addition with several organometallic reagents to tricyclic lactone (-)-1 proceeded diastereoselectively. Newly generated tertiary and quaternary asymmetric centers were controlled by the order in which the nucleophilic reagents were added. Using this methodology, enantiodivergent syntheses of several gamma-substituted butenolides with tertiary and quaternary asymmetric centers were established from a single chiral material. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.