(4a'R,9a'R)-11'-(cyclopropylmethyl)-6'-methoxy-1',2'-dihydro-4'H,9'H-spiro[[1,3]dioxolane-2,3'-[4a,9a](ethanoiminomethano)fluorene]-10'-carbonitrile | 1069111-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4a'R,9a'R)-11'-(cyclopropylmethyl)-6'-methoxy-1',2'-dihydro-4'H,9'H-spiro[[1,3]dioxolane-2,3'-[4a,9a](ethanoiminomethano)fluorene]-10'-carbonitrile
• CAS: 1069111-51-8
• 化学式: C₂₄H₃₀N₂O₃
• 分子量: 394.514
• InChiKey: FXOSGQYXMPUJRZ-ATTQYFOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.72
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4a'R,9a'R)-11'-(cyclopropylmethyl)-6'-methoxy-1',2'-dihydro-4'H,9'H-spiro[[1,3]dioxolane-2,3'-[4a,9a](ethanoiminomethano)fluorene]-10'-carbonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以74%的产率得到(1'R,9'R)-11'-(cyclopropylmethyl)-4'-methoxyspiro[1,3-dioxolane-2,15'-11-azatetracyclo[7.4.4.01,9.02,7]heptadeca-2(7),3,5-triene]
  参考文献：
  名称：

  Synthesis of a Stable Iminium Salt and Propellane Derivatives

  摘要：

  The treatment of morphinan I with NaH and MsCl provided very stable iminium salt 7 possessing propellane skeleton. One of the synthesized iminium salts 7, isobutyl derivative 7b, was crystallized and its structure was determined by X-ray crystallography. The natural bond orbital analysis suggested that the stability of the iminium should result from the stereoelectronic effect (hyperconjugation) attributed to their own structures.

  DOI：

  10.1021/jo801276z
• 作为产物：
  描述：

  、 氰化钠 以 水 为溶剂， 生成 (4a'R,9a'R)-11'-(cyclopropylmethyl)-6'-methoxy-1',2'-dihydro-4'H,9'H-spiro[[1,3]dioxolane-2,3'-[4a,9a](ethanoiminomethano)fluorene]-10'-carbonitrile
  参考文献：
  名称：

  Synthesis of a Stable Iminium Salt and Propellane Derivatives

  摘要：

  The treatment of morphinan I with NaH and MsCl provided very stable iminium salt 7 possessing propellane skeleton. One of the synthesized iminium salts 7, isobutyl derivative 7b, was crystallized and its structure was determined by X-ray crystallography. The natural bond orbital analysis suggested that the stability of the iminium should result from the stereoelectronic effect (hyperconjugation) attributed to their own structures.

  DOI：

  10.1021/jo801276z