(3aS,4R,7R,7aS,8R)-7-Nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-indene-8-carbaldehyde | 205248-17-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (3aS,4R,7R,7aS,8R)-7-Nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-indene-8-carbaldehyde
• CAS: 205248-17-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: BMPXBIFDGZHNMP-HTFCKZLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aS,4R,7R,7aS,8R)-7-Nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-indene-8-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以86%的产率得到
  参考文献：
  名称：

  Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

  摘要：

  The 1-glyco-2-nitrocyclohexa-2,4-dienes 1a and 5a react with cyclopentadiene to yield, almost exclusively, the 10-glyco-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes 4a and 8a. Formation of these products is explained as the result of a tandem consecutive asymmetric Diels-Alder reaction-Cope rearrangement. Periodate oxidation of deprotected sugar side-chains, followed by sodium borohydride reduction yielded enantiomerically pure 10-formyl- and 10-hydroxymethyl-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes. Structures have been determined by X-ray crystallographic and spectroscopic analyses, and chemical correlation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00627-7
• 作为产物：
  描述：

  在 sodium periodate 作用下， 以 水 为溶剂， 反应 0.25h， 以77%的产率得到(3aS,4R,7R,7aS,8R)-7-Nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-indene-8-carbaldehyde
  参考文献：
  名称：

  Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

  摘要：

  The 1-glyco-2-nitrocyclohexa-2,4-dienes 1a and 5a react with cyclopentadiene to yield, almost exclusively, the 10-glyco-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes 4a and 8a. Formation of these products is explained as the result of a tandem consecutive asymmetric Diels-Alder reaction-Cope rearrangement. Periodate oxidation of deprotected sugar side-chains, followed by sodium borohydride reduction yielded enantiomerically pure 10-formyl- and 10-hydroxymethyl-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes. Structures have been determined by X-ray crystallographic and spectroscopic analyses, and chemical correlation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00627-7