(3S,3aS,4aS,9aS)-3-Methyl-4-[2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-eth-(Z)-ylidene]-3a,4,4a,5,6,7,8,9a-octahydro-3H-naphtho[2,3-c]furan-1-one | 745021-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3S,3aS,4aS,9aS)-3-Methyl-4-[2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-eth-(Z)-ylidene]-3a,4,4a,5,6,7,8,9a-octahydro-3H-naphtho[2,3-c]furan-1-one
• CAS: 745021-40-3
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: BFWLLXLCNDBKTL-NJPIXWDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 (3S,3aS,4aS,9aS)-3-Methyl-4-[2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-eth-(Z)-ylidene]-3a,4,4a,5,6,7,8,9a-octahydro-3H-naphtho[2,3-c]furan-1-one 以93%的产率得到(R)-1,1,2,2-Tetramethyl-5-{2-[(3S,3aS,4aS,9aS)-3-methyl-1-oxo-3,3a,4a,5,6,7,8,9a-octahydro-1H-naphtho[2,3-c]furan-(4Z)-ylidene]-ethyl}-pyrrolidinium; iodide
  参考文献：
  名称：

  Himbacine analogs as muscarinic receptor antagonists––effects of tether and heterocyclic variations

  摘要：

  A number of analogs of the natural product himbacine were synthesized employing variations at the heterocyclic unit and the tether that links the heterocyclic unit to the tricyclic motif. Several of these analogs had M-2 affinity and M-1/M-2 selectivity comparable to those of himbacine. The structural and stereochemical requirements of the heterocyclic unit for muscarinic binding are discussed in the light of these data. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.047
• 作为产物：
  描述：

  (E)-3-Cyclohex-1-enyl-acrylic acid (Z)-(S)-1-methyl-penta-2,4-dienyl ester 在 Ra-Ni 氢气 作用下， 以 甲苯 为溶剂， 生成 (3S,3aS,4aS,9aS)-3-Methyl-4-[2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-eth-(Z)-ylidene]-3a,4,4a,5,6,7,8,9a-octahydro-3H-naphtho[2,3-c]furan-1-one
  参考文献：
  名称：

  Himbacine analogs as muscarinic receptor antagonists––effects of tether and heterocyclic variations

  摘要：

  A number of analogs of the natural product himbacine were synthesized employing variations at the heterocyclic unit and the tether that links the heterocyclic unit to the tricyclic motif. Several of these analogs had M-2 affinity and M-1/M-2 selectivity comparable to those of himbacine. The structural and stereochemical requirements of the heterocyclic unit for muscarinic binding are discussed in the light of these data. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.047