(2R)-2-[(1R,3S)-3-methyl-2-methylidenecyclopentyl]-N-[(1S)-1-phenylethyl]propan-1-amine | 176325-80-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-[(1R,3S)-3-methyl-2-methylidenecyclopentyl]-N-[(1S)-1-phenylethyl]propan-1-amine
• CAS: 176325-80-7
• 化学式: C₁₈H₂₇N
• 分子量: 257.419
• InChiKey: AAIHVTLEPWOAED-ILXVDBEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (2R)-2-[(1R,3S)-3-methyl-2-methylidenecyclopentyl]-N-[(1S)-1-phenylethyl]propan-1-amine 在 palladium dihydroxide hydroxide 、 氢气 、 双氧水 、 氰基亚甲基三甲基膦 、 儿萘酚硼烷 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.0h， 生成 (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
• 作为产物：
  描述：

  (2R)-2-[(1R,3S)-3-methyl-2-methylidenecyclopentyl]-N-[(1S)-1-phenylethyl]propanamide 在 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 为溶剂， 以80%的产率得到(2R)-2-[(1R,3S)-3-methyl-2-methylidenecyclopentyl]-N-[(1S)-1-phenylethyl]propan-1-amine
  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

• 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