(3S,3aR,4R,4aS,8aR,9aS)-4-[(S)-1-Hydroxy-2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-ethyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one | 745021-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3S,3aR,4R,4aS,8aR,9aS)-4-[(S)-1-Hydroxy-2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-ethyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one
• 英文别名: (3S,3aR,4R,4aS,8aR,9aS)-4-[(1S)-1-hydroxy-2-[(2R)-1,5,5-trimethylpyrrolidin-2-yl]ethyl]-3-methyl-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one
• CAS: 745021-36-7
• 化学式: C₂₂H₃₇NO₃
• 分子量: 363.541
• InChiKey: MSKMNIYJSITCIE-XSWYFRFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,3aR,4R,4aS,8aR,9aS)-4-[(S)-1-Hydroxy-2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-ethyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one 在 氯化亚砜 作用下， 以 苯 为溶剂， 以75%的产率得到(3S,3aS,4aS,8aR,9aS)-3-Methyl-4-[2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-eth-(Z)-ylidene]-decahydro-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
• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 在 platinum(IV) oxide 、 Ra-Ni 氢气 作用下， 以 甲苯 为溶剂， 生成 (3S,3aR,4R,4aS,8aR,9aS)-4-[(S)-1-Hydroxy-2-((R)-1,5,5-trimethyl-pyrrolidin-2-yl)-ethyl]-3-methyl-decahydro-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

文献信息

• Himbacine analogs as muscarinic receptor antagonists––effects of tether and heterocyclic variations
  作者：Samuel Chackalamannil、Darı́o Doller、Robert McQuade、Vilma Ruperto

  DOI：10.1016/j.bmcl.2004.05.047

  日期：2004.8

  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.