(2S,6R)-2-Methyl-6-[(Z)-2-((3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester | 475273-05-3

• 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: (2S,6R)-2-Methyl-6-[(Z)-2-((3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,6S)-2-[(Z)-2-[(3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-4-yl]ethenyl]-6-methylpiperidine-1-carboxylate
• CAS: 475273-05-3
• 化学式: C₂₆H₄₁NO₄
• 分子量: 431.616
• InChiKey: QNYKAHUMLTWFJY-BFJAMPTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-Methyl-6-[(Z)-2-((3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,3aR,4S,4aR,8aR,9aS)-3-Methyl-4-[(Z)-2-((2R,6S)-6-methyl-piperidin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one
  参考文献：
  名称：

  Synthesis and affinity studies of himbacine derived muscarinic receptor antagonists

  摘要：

  A series of himbacine (1)-related analogues has been prepared featuring three different isomeric configurations with respect to the B-ring (a, b and natural c) and three different interconnecting two-carbon unsaturated units [natural (E)-ene, (Z)-ene, and yne]. The study of the binding affinities of the nine resulting compounds, including synthetic (+)-himbacine (3c), towards the M-1-M-4 muscarine receptor subtypes revealed that analogues 3a and 5c display a promising 10-fold selectivity for the M-2 receptor as compared to the M, receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00315-3
• 作为产物：
  描述：

  (2S,6R)-2-Methyl-6-((3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylethynyl)-piperidine-1-carboxylic acid tert-butyl ester 在 镍 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,6R)-2-Methyl-6-[(Z)-2-((3S,3aR,4S,4aR,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and affinity studies of himbacine derived muscarinic receptor antagonists

  摘要：

  A series of himbacine (1)-related analogues has been prepared featuring three different isomeric configurations with respect to the B-ring (a, b and natural c) and three different interconnecting two-carbon unsaturated units [natural (E)-ene, (Z)-ene, and yne]. The study of the binding affinities of the nine resulting compounds, including synthetic (+)-himbacine (3c), towards the M-1-M-4 muscarine receptor subtypes revealed that analogues 3a and 5c display a promising 10-fold selectivity for the M-2 receptor as compared to the M, receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00315-3

文献信息

• Synthesis and affinity studies of himbacine derived muscarinic receptor antagonists
  作者：Ling-Jie Gao、Magali Waelbroeck、Sven Hofman、Dirk Van Haver、Marco Milanesio、Davide Viterbo、Pierre J De Clercq

  DOI：10.1016/s0960-894x(02)00315-3

  日期：2002.8

  A series of himbacine (1)-related analogues has been prepared featuring three different isomeric configurations with respect to the B-ring (a, b and natural c) and three different interconnecting two-carbon unsaturated units [natural (E)-ene, (Z)-ene, and yne]. The study of the binding affinities of the nine resulting compounds, including synthetic (+)-himbacine (3c), towards the M-1-M-4 muscarine receptor subtypes revealed that analogues 3a and 5c display a promising 10-fold selectivity for the M-2 receptor as compared to the M, receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.