N,N-diallyl-2,4,9,9a-tetrahydro-1H-cyclopenta[b]naphthalen-9-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: N,N-diallyl-2,4,9,9a-tetrahydro-1H-cyclopenta[b]naphthalen-9-amine
• 英文别名: (3aR,4S)-N,N-bis(prop-2-enyl)-3,3a,4,9-tetrahydro-2H-cyclopenta[b]naphthalen-4-amine
• 化学式: C₁₉H₂₃N
• 分子量: 265.398
• InChiKey: LMXRJUQIIBAMRC-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-diallyl-2,4,9,9a-tetrahydro-1H-cyclopenta[b]naphthalen-9-amine 、 N-甲基苄胺 在 磷酸二苯酯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以70%的产率得到N-benzyl-N-methyl-2,4,9,9a-tetrahydro-1H-cyclopenta[b]naphthalen-9-amine
  参考文献：
  名称：

  Domino Formation of Enamines - Intramolecular Cyclizations to 1-Aminotetralins from γ-Arylallene Aldehydes and Amines

  摘要：

  1,5-/1,6-Allenals conjugated to an aromatic ring undergo a cyclization, in the presence of an amine, that leads to tricyclic compounds including the 1-aminotetralin scaffold. This domino process combines the in situ formation of the enamine and the cyclization affording the tricyclic 1-aminotetralins in very high diastereoselectivities.

  DOI：

  10.1021/ol5026712
• 作为产物：
  描述：

  7-phenylhepta-5,6-dien-1-ol 在 草酰氯 、 磷酸二苯酯 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 17.0h， 生成 N,N-diallyl-2,4,9,9a-tetrahydro-1H-cyclopenta[b]naphthalen-9-amine
  参考文献：
  名称：

  Domino Formation of Enamines - Intramolecular Cyclizations to 1-Aminotetralins from γ-Arylallene Aldehydes and Amines

  摘要：

  1,5-/1,6-Allenals conjugated to an aromatic ring undergo a cyclization, in the presence of an amine, that leads to tricyclic compounds including the 1-aminotetralin scaffold. This domino process combines the in situ formation of the enamine and the cyclization affording the tricyclic 1-aminotetralins in very high diastereoselectivities.

  DOI：

  10.1021/ol5026712

文献信息

• Reactions Involving Tryptamines and δ-Allenyl Aldehydes: Competition between Pictet-Spengler Reaction and Cyclization to 1-Aminotetralins
  作者：Valérian Gobé、Vincent Gandon、Xavier Guinchard

  DOI：10.1002/adsc.201701487

  日期：2018.3.20

  course of Pictet‐Spengler reactions between tryptamines and δ‐allenyl aldehydes. This discovery led to the study of a novel reactivity using aldehydes and secondary amines. DFT calculations show that the cyclization occurs in a stepwise manner that is sufficiently fast to allow high diastereoselectivity. When using allyl‐tryptamines, it is possible to control the reaction, depending on the substituents

  在色胺和δ-烯基醛之间的Pictet-Spengler反应过程中意外地观察到1-氨基四氢萘的分离。这一发现导致了对使用醛和仲胺的新型反应性的研究。DFT计算表明，环化以足够快的步长方式发生，以实现高非对映选择性。当使用烯丙基色胺时，可以根据取代基控制反应，以得到1-氨基四氢化萘或四氢β-咔啉。通过DFT计算研究了这些竞争反应性。
• Domino Formation of Enamines - Intramolecular Cyclizations to 1-Aminotetralins from γ-Arylallene Aldehydes and Amines
  作者：Valérian Gobé、Pascal Retailleau、Xavier Guinchard

  DOI：10.1021/ol5026712

  日期：2014.10.17

  1,5-/1,6-Allenals conjugated to an aromatic ring undergo a cyclization, in the presence of an amine, that leads to tricyclic compounds including the 1-aminotetralin scaffold. This domino process combines the in situ formation of the enamine and the cyclization affording the tricyclic 1-aminotetralins in very high diastereoselectivities.