(Z)-(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester | 283612-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester
• 英文别名: (E)-(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester；[(1R,2S)-2-phenylcyclohexyl] (1S,9R,13E)-13-ethylidene-5-methoxy-11-methylidene-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-1-carboxylate
• CAS: 283612-41-9
• 化学式: C₂₉H₃₃NO₃
• 分子量: 443.586
• InChiKey: YUBQVSFTGYFMHR-NIOGLDEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester 在 三氟甲磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以88%的产率得到(1S,9S)-13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2,4,6,10-tetraene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
  参考文献：
  名称：

  Asymmetric palladium annulation: formal synthesis of (+)-huperzine A

  摘要：

  A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1R,2S)-2-phenylcyclohexanol derived beta-ketoester 14. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01874-2
• 作为产物：
  描述：

  (1R,2S)-trans-2-phenylcyclohexanol 在 四(三苯基膦)钯 、 偶氮二异丁腈 、 potassium tert-butylate 、 苯硫酚 、 APTS 、 四甲基胍 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 、 苯 为溶剂， 反应 234.0h， 生成 (Z)-(5S)-11-ethylidene-7,8,9,10-tetrahydro-2-methoxy-7-methylene-5,9-methanocycloocta[b]pyridine-5(6H)carboxylic acid, (1R,2S)-2-phenylcyclohexyl ester
  参考文献：
  名称：

  Asymmetric palladium annulation: formal synthesis of (+)-huperzine A

  摘要：

  A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1R,2S)-2-phenylcyclohexanol derived beta-ketoester 14. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01874-2

文献信息

• A Formal Synthesis of (+)-Huperzine A
  作者：Arnaud Haudrechy、Christophe Chassaing、Claude Riche、Yves Langlois

  DOI：10.1016/s0040-4020(00)00227-1

  日期：2000.5

  A new formal stereoselective synthesis of (+)-Huperzine A (1) was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1R,2S)-2-phenylcyclohexanol derived beta-ketoester 2c. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric palladium annulation: formal synthesis of (+)-huperzine A
  作者：Christophe Chassaing、Arnaud Haudrechy、Yves Langlois

  DOI：10.1016/s0040-4039(99)01874-2

  日期：1999.12

  A new formal stereoselective synthesis of (+)-huperzine A 1 was achieved using as a key step a palladium mediated annulation between 2-methylene-1,3-propanediol diacetate and (1R,2S)-2-phenylcyclohexanol derived beta-ketoester 14. (C) 1999 Elsevier Science Ltd. All rights reserved.