(4bR,8aS,9R)-11-(cyclopropylmethyl)-8a-hydroxy-3-methoxy-4-phenoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one | 1069111-43-8

• 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: (4bR,8aS,9R)-11-(cyclopropylmethyl)-8a-hydroxy-3-methoxy-4-phenoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one
• CAS: 1069111-43-8
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: RHGOORFNFRYFJD-XSBVVTFOSA-N

物化性质

• 熔点：
  169-171 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  589.0±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4bR,8aS,9R)-11-(cyclopropylmethyl)-8a-hydroxy-3-methoxy-4-phenoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one 、 乙二醇 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以92%的产率得到(4b'R,8a'S,9'R)-11'-(cyclopropylmethyl)-3'-methoxy-4'-phenoxy-7',8',9',10'-tetrahydro-5'H,8a'H-spiro[[1,3]dioxolane-2,6'-[9,4b](epiminoethano)phenanthren]-8a'-ol
  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：

  溴苯 、 (4bR,8aS,9R)-11-(cyclopropylmethyl)-4,8a-dihydroxy-3-methoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one 在 吡啶 、 铜 、 potassium carbonate 作用下， 反应 13.5h， 以84%的产率得到(4bR,8aS,9R)-11-(cyclopropylmethyl)-8a-hydroxy-3-methoxy-4-phenoxy-8,8a,9,10-tetrahydro-5H-9,4b-(epiminoethano)phenanthren-6(7H)-one
  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