(R)-1-((1S,2R,3S,4R)-3-Hydroxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-ethanol | 528609-59-8

• 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)-ethanol
• 英文别名: (1R)-1-[(1S,2R,3S,4R)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]ethanol
• CAS: 528609-59-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: GGOXZOIAIGTWBD-MQIGXGKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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)-ethanol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 、 邻二氯苯 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-β-angelica lactone
  参考文献：
  名称：

  Enantiodivergent syntheses of γ-substituted butenolides with tertiary and quaternary asymmetric centers

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(02)02711-9
• 作为产物：
  描述：

  (1R,2S,3R,4S)-3-Acetyl-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)-ethanol
  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 new acetal aza-cage compounds via ozonolysis of bis-endo-diol- and diacylnorbornene derivatives
  作者：Chung-Yi Wu、Hui-Chang Lin、Hsien-Jen Wu

  DOI：10.1016/j.tet.2012.01.055

  日期：2012.3

  We synthesized acetal aza-cage compounds directly via ozonolysis of 2,3-bis-endo-diol- and diacylnorbornenes in dichloromethane at −78 °C. Ozonolysis of the diols followed by addition of amines gave the aza-cage compounds in high yields. The reaction mechanism for the formation of this type of aza-cage compounds is proposed to proceed via the hydroperoxide intermediate. Ozonolysis of the diacetyl norbornene

  我们在−78°C下通过在二氯甲烷中进行2,3-双-内-二醇-和二酰基吲哚冰片的臭氧分解直接合成了缩醛氮杂笼化合物。二醇的臭氧分解，然后加入胺，以高收率得到了氮杂笼型化合物。建议通过氢过氧化物中间体进行形成这种氮杂笼型化合物的反应机理。双乙酰降冰片烯的臭氧分解，然后加入（1）伯胺，得到单氮杂笼和二氮杂-保持架，（2）的叔丁胺生成羟基内酯和二氮杂笼，（3）氨基酸酯生成光学活性的氮杂笼，其中一种化合物转化为手性氨基醇，另一种化合物的结构通过X射线分析证实。提出了通过最终的臭氧化物和亚胺中间体的机理来形成这种氮杂笼。
• 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.