(1S,8aS)-1-(4-Bromo-pyridin-3-ylmethyl)-2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,2,3,4,6,7,8,8a-octahydro-isoquinoline | 200629-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: (1S,8aS)-1-(4-Bromo-pyridin-3-ylmethyl)-2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,2,3,4,6,7,8,8a-octahydro-isoquinoline
• 英文别名: (1S,8aS)-1-[(4-bromopyridin-3-yl)methyl]-2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)-3,4,6,7,8,8a-hexahydro-1H-isoquinoline
• CAS: 200629-25-0
• 化学式: C₃₀H₃₁BrN₂
• 分子量: 499.494
• InChiKey: QGMXXSRFMGQTGJ-SVEHJYQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,8aS)-1-(4-Bromo-pyridin-3-ylmethyl)-2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,2,3,4,6,7,8,8a-octahydro-isoquinoline 在 palladium (II) bis(triphenylphosphine) bis(trifluoroacetate) 、 N,N-二异丙基乙胺 作用下， 以 xylene 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  Pyridinomorphinans: Asymmetric synthesis of either enantiomer and opioid receptor binding selectivity

  摘要：

  Either enantiomer of a new class of morphinans in which the aryl ring is replaced by a pyridine ring can be prepared by sequential iminium ion-allylsilane cyclization and intramolecular Heck insertion. Pyridinomorphinan 5 exhibits high affinity for the mu opioid receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10274-x
• 作为产物：
  描述：

  3-allyl-4-bromopyridine 在 sodium periodate 、 四氧化锇 、 zinc(II) iodide 、 potassium hexacyanoferrate(III) 作用下， 生成 (1S,8aS)-1-(4-Bromo-pyridin-3-ylmethyl)-2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1,2,3,4,6,7,8,8a-octahydro-isoquinoline
  参考文献：
  名称：

  Pyridinomorphinans: Asymmetric synthesis of either enantiomer and opioid receptor binding selectivity

  摘要：

  Either enantiomer of a new class of morphinans in which the aryl ring is replaced by a pyridine ring can be prepared by sequential iminium ion-allylsilane cyclization and intramolecular Heck insertion. Pyridinomorphinan 5 exhibits high affinity for the mu opioid receptor. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10274-x

文献信息

• Pyridinomorphinans: Asymmetric synthesis of either enantiomer and opioid receptor binding selectivity
  作者：Chang Y. Hong、Larry E. Overman、Alex Romero

  DOI：10.1016/s0040-4039(97)10274-x

  日期：1997.12

  Either enantiomer of a new class of morphinans in which the aryl ring is replaced by a pyridine ring can be prepared by sequential iminium ion-allylsilane cyclization and intramolecular Heck insertion. Pyridinomorphinan 5 exhibits high affinity for the mu opioid receptor. (C) 1997 Elsevier Science Ltd.