(4R,4aR,7S,7aR)-4,7-二甲基八氢-1H-环戊二烯并[c]吡啶 | 176486-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: (4R,4aR,7S,7aR)-4,7-二甲基八氢-1H-环戊二烯并[c]吡啶
• 英文名称: nor-α-skytanthine
• 英文别名: (4R,4aR,7S,7aR)-4,7-dimethyloctahydro-1H-cyclopenta[c]pyridine；(4R,4aR,7S,7aR)-4,7-dimethyl-2,3,4,4a,5,6,7,7a-octahydro-1H-cyclopenta[c]pyridine
• CAS: 176486-94-5
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: XFDFLVUGOJZRPW-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (4R,4aR,7S,7aR)-4,7-二甲基八氢-1H-环戊二烯并[c]吡啶 在 甲酸 作用下， 以82%的产率得到(+)-α-skytanthine
  参考文献：
  名称：

  Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

  摘要：

  Cyanomethylenetributylphosphorane was shown to mediate the dehydrocyclization of diols and amino alcohols to give the corresponding 6-membered O- and N-heterocycles in 90% or better yields. Using the reaction as a key step, (+)-alpha-skytanthine, a unique mono terpene alkaloid was synthesized stereoselectively. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00319-x
• 作为产物：
  描述：

  (4R,4aR,7S,7aR)-4,7-dimethyl-2-[(1S)-1-phenylethyl]-1,3,4,4a,5,6,7,7a-octahydrocyclopenta[c]pyridine 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 以91%的产率得到(4R,4aR,7S,7aR)-4,7-二甲基八氢-1H-环戊二烯并[c]吡啶
  参考文献：
  名称：

  Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

  摘要：

  Cyanomethylenetributylphosphorane was shown to mediate the dehydrocyclization of diols and amino alcohols to give the corresponding 6-membered O- and N-heterocycles in 90% or better yields. Using the reaction as a key step, (+)-alpha-skytanthine, a unique mono terpene alkaloid was synthesized stereoselectively. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00319-x

文献信息

• Stereocontrolled synthesis of (+)-α-skytanthine by means of an intramolecular Pauson–Khand reaction
  作者：Kyosuke Kaneda、Toshio Honda

  DOI：10.1016/j.tet.2008.10.029

  日期：2008.12

  Diastereoselective synthesis of (+)-α-skytanthine was established by means of an intramolecular Pauson–Khand reaction of N-but-2-yn-1-yl-N-[(2R)-2-methylbut-3-en-1-yl]-1-(2-nitrobenzene)sulfonamide, in which the newly generated stereogenic center was stereoselectively constructed to be R by reflection of the stereochemistry of the methyl group in the starting material.

  通过N -but-2-yn-1-yl- N -[（2 R）-2-甲基but-3-en- 1-基] -1-（2-硝基苯）磺酰胺，其中新生成的立体异构中心通过反映起始原料中甲基的立体化学而被立体选择性地构建为R。
• Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine
  作者：Tetsuto Tsunoda、Fumie Ozaki、Nozomi Shirakata、Yuki Tamaoka、Hidetoshi Yamamoto、Shô Itô

  DOI：10.1016/0040-4039(96)00319-x

  日期：1996.4

  Cyanomethylenetributylphosphorane was shown to mediate the dehydrocyclization of diols and amino alcohols to give the corresponding 6-membered O- and N-heterocycles in 90% or better yields. Using the reaction as a key step, (+)-alpha-skytanthine, a unique mono terpene alkaloid was synthesized stereoselectively. Copyright (C) 1996 Elsevier Science Ltd