(1R,4S,10S)-(1-ethyloctahydroquinolizin-4-yl)methanol | 957777-80-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (1R,4S,10S)-(1-ethyloctahydroquinolizin-4-yl)methanol
• 英文别名: [(1R,4S,9aS)-1-ethyl-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-4-yl]methanol
• CAS: 957777-80-9
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: SQAUTNDRQOPHPS-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4S,10S)-(1-ethyloctahydroquinolizin-4-yl)methanol 生成
  参考文献：
  名称：

  Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors

  摘要：

  We previously reported that the synthetic quinolizidine 1-epi-2071 is a relatively selective blocker of 0 nicotinic acetylcholine receptors. We now synthesized the analogous poison frog alkaloids 233A, 235U, and 251AA, and investigated the biological activities at two major types of neuronal nicotinic receptors. Electrophysiological study showed that the alkaloid 233A blocked alpha 7 and alpha 4 beta 2 currents with similar potencies. Alkaloids 235U and 251AA also showed similar potencies for blockade of a7 and alpha 4 beta 2 currents. Thus, based on these studies, it would appear that C4 substituents greater in length than the allyl of 1-epi-2071 reduce alpha 7-potency without affecting alpha 4 beta 2-potency. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.045
• 作为产物：
  描述：

  (2S,6S)-1-But-3-enoyl-5,6-divinyl-piperidine-2-carboxylic acid methyl ester 在 platinum(IV) oxide RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (1R,4S,10S)-(1-ethyloctahydroquinolizin-4-yl)methanol
  参考文献：
  名称：

  Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid

  摘要：

  A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.

  DOI：

  10.1021/ja039919j

文献信息

• Amidopalladation of Alkoxyallenes Applied in the Synthesis of an Enantiopure 1-Ethylquinolizidine Frog Alkaloid
  作者：Sape S. Kinderman、René de Gelder、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra、Floris P. J. T. Rutjes

  DOI：10.1021/ja039919j

  日期：2004.4.1

  A palladium-catalyzed amidation of alkoxyallenes has been developed for the construction of linear allylic N,O-acetals under basic conditions involving (cyclic) amides, sulfonamides, carbamates, and amidophosphates. Application of the methodology provided access to the enantiopure 1-ethylquinolizidine structural motif, which is a key synthon in the synthesis of the naturally occurring poisonous frog quinolizidine 233A and derivatives such as the 1-epi-isomer of quinolizidine 207I.
• Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors
  作者：Naoki Toyooka、Soushi Kobayashi、Dejun Zhou、Hiroshi Tsuneki、Tsutomu Wada、Hideki Sakai、Hideo Nemoto、Toshiyasu Sasaoka、H. Martin Garraffo、Thomas F. Spande、John W. Daly

  DOI：10.1016/j.bmcl.2007.08.045

  日期：2007.11

  We previously reported that the synthetic quinolizidine 1-epi-2071 is a relatively selective blocker of 0 nicotinic acetylcholine receptors. We now synthesized the analogous poison frog alkaloids 233A, 235U, and 251AA, and investigated the biological activities at two major types of neuronal nicotinic receptors. Electrophysiological study showed that the alkaloid 233A blocked alpha 7 and alpha 4 beta 2 currents with similar potencies. Alkaloids 235U and 251AA also showed similar potencies for blockade of a7 and alpha 4 beta 2 currents. Thus, based on these studies, it would appear that C4 substituents greater in length than the allyl of 1-epi-2071 reduce alpha 7-potency without affecting alpha 4 beta 2-potency. (c) 2007 Elsevier Ltd. All rights reserved.