(1S,2R)-trans-1-(cyanomethyl)-2-isopropyl-1,2-dihydronaphthalene | 160845-54-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (1S,2R)-trans-1-(cyanomethyl)-2-isopropyl-1,2-dihydronaphthalene
• 英文别名: 2-[(1S,2R)-2-propan-2-yl-1,2-dihydronaphthalen-1-yl]acetonitrile
• CAS: 160845-54-5
• 化学式: C₁₅H₁₇N
• 分子量: 211.307
• InChiKey: AQAHGOKUBUMOEU-ZFWWWQNUSA-N

物化性质

• 沸点：
  361.3±11.0 °C(predicted)
• 密度：
  0.993±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R)-trans-1-(cyanomethyl)-2-isopropyl-1,2-dihydronaphthalene 在 lithium aluminium tetrahydride 、 三乙醇胺 作用下， 以 四氢呋喃 为溶剂， 生成 Benzyl-[2-((1S,2R)-2-isopropyl-1,2-dihydro-naphthalen-1-yl)-ethyl]-amine
  参考文献：
  名称：

  A novel asymmetric synthesis of 3-benzyl-1,2,3,4,5,6-hexahydro-11-alkyl-2,6-methano-3-benzazocines

  摘要：

  9-烷基-6,7-苄莫沙芬（1,2,3,4,5,6-六氢-11-烷基-2,6-亚甲基-3-苄唑辛）是σ受体位点的重要选择性配体；以（1R, 2R）-或（1S, 2S）-1-羟甲基-2-烷基-2-烷基-1,2-二氢萘为起始原料的不对称合成方法已被描述。

  DOI：

  10.1039/c39940002401
• 作为产物：
  描述：

  [(1S,2R)-2-propan-2-yl-1,2-dihydronaphthalen-1-yl]methanol 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (1S,2R)-trans-1-(cyanomethyl)-2-isopropyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  Asymmetric Synthesis of 9-Alkyl-2-benzyl-6,7-benzomorphans:  Characterization as Novel σ Receptor Ligands

  摘要：

  A convenient enantioselective synthesis of (1R,5R,9R)- and (1S,5S,9S)-9-alkyl-2-benzyl-6,7-benzomorphans (2a-c) which starts with naphthaldehyde is described. These compounds were designed to gain additional information on the structure-a binding relationship of the 6,7-benzomorphan class of a ligands. In contrast to pentazocine and most 6,7-benzomorphans, the (1R,5R,9R)-isomers of 2a-c showed greater affinity for the al receptor than the (1S,5S,9S)isomers. Despite reversal of enantioselectivity at the ax sites, moderate affinity and enantioselectivity at the sigma(2) sites [greater affinity for (1R,5R,9R)-isomers than (1S,5S,9S)-isomers] were maintained. A comparison of the binding affinities of 2a-e to the more conformationally flexible trans-2-alkyl-1-benzaminoethyl-1,2-dihydronaphthalenes (10a-c) suggested that the relatively rigid structure of 2a-c played an important part in their al binding properties. These compounds, particularly (1R,5R,SR)-2-benzyl-9-methyl-6,7-benzomorphan [(-)-2a], which has a Ki value of 0.96 nM, will be useful in further characterization of the al receptor.

  DOI：

  10.1021/jm990169r

文献信息

• Bai Xu, Mascarella S. Wayne, Bowen Wayne D., Carroll F. Ivy,, J. Chem. Soc. Chem. Commun, (1994) N 20, S 2401-2402
  作者：Bai Xu, Mascarella S. Wayne, Bowen Wayne D., Carroll F. Ivy,

  DOI：——

  日期：——