(1R,4S)-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-one | 1265966-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S)-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-one
• 英文别名: (1'R,4'S)-spiro[1,3-dioxolane-2,6'-bicyclo[2.2.2]octane]-2'-one
• CAS: 1265966-48-0
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: HNODUDDBMMMSGS-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4S)-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-one 在 吡啶 、 iron(III) chloride 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 甲酸 、 硫酸 、 盐酸羟胺 、 sodium acetate 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 、 臭氧 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 11.83h， 生成 1-benzyl-2-methyl (2S,5S)-5-(hydroxymethyl)azepane-1,2-dicarboxylate
  参考文献：
  名称：

  An Asymmetric Synthesis of (2S,5S)-5-Substituted Azepane-2-Carboxylate Derivatives

  摘要：

  To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and CS substituents in a stereoselective manner.

  DOI：

  10.1021/jo102475s
• 作为产物：
  描述：

  (1R,4S,6S)-6-oxobicyclo[2.2.2]oct-2-yl benzoate 在 四丙基高钌酸铵 、 lithium hydroxide monohydrate 、 水 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 50.5h， 生成 (1R,4S)-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-one
  参考文献：
  名称：

  An Asymmetric Synthesis of (2S,5S)-5-Substituted Azepane-2-Carboxylate Derivatives

  摘要：

  To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and CS substituents in a stereoselective manner.

  DOI：

  10.1021/jo102475s

文献信息

• An Asymmetric Synthesis of (2<i>S</i>,5<i>S</i>)-5-Substituted Azepane-2-Carboxylate Derivatives
  作者：Donn G. Wishka、Marion Bédard、Katherine E. Brighty、Richard A. Buzon、Kathleen A. Farley、Michael W. Fichtner、Goss S. Kauffman、Jaap Kooistra、Jason G. Lewis、Hardwin O’Dowd、Ivan J. Samardjiev、Brian Samas、Geeta Yalamanchi、Mark C. Noe

  DOI：10.1021/jo102475s

  日期：2011.3.18

  To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and CS substituents in a stereoselective manner.