(1R,2S)-trans-2-isopropyl-1,2-dihydronaphthalene-1-carboxaldehyde | 160962-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-trans-2-isopropyl-1,2-dihydronaphthalene-1-carboxaldehyde
• 英文别名: (1R,2S)-2-propan-2-yl-1,2-dihydronaphthalene-1-carbaldehyde
• CAS: 160962-05-0
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: WPEAJZSLAUOVFX-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S)-trans-2-isopropyl-1,2-dihydronaphthalene-1-carboxaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (+)-trans-1-(hydroxymethyl)-2-isopropyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  Stereospecific conjugate addition of organolithium reagents to naphthylimines. A facile route to 1,1,2- and 1,2-substituted dihydroronaphthalenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)96707-8
• 作为产物：
  描述：

  异丙基氯化镁 、 (4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到(1R,2S)-trans-2-isopropyl-1,2-dihydronaphthalene-1-carboxaldehyde
  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

• MEYERS, A. I.;BROWN, JACK D.;LAUCHER, DOMINIQUE, TETRAHEDRON LETT., 28,(1987) N 44, 5283-5286
  作者：MEYERS, A. I.、BROWN, JACK D.、LAUCHER, DOMINIQUE

  DOI：——

  日期：——
• MEYERS, A. I.;BROWN, JACK D.;LAUCHER, DOMINIQUE, TETRAHEDRON LETT., 28,(1987) N 44, 5279-5282
  作者：MEYERS, A. I.、BROWN, JACK D.、LAUCHER, DOMINIQUE

  DOI：——

  日期：——
• Asymmetric Synthesis of 9-Alkyl-2-benzyl-6,7-benzomorphans:  Characterization as Novel σ Receptor Ligands
  作者：F. Ivy Carroll、Xu Bai、Ali Dehghani、S. Wayne Mascarella、Wanda Williams、Wayne D. Bowen

  DOI：10.1021/jm990169r

  日期：1999.11.1

  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.
• Stereospecific conjugate addition of organolithium reagents to naphthylimines. A facile route to 1,1,2- and 1,2-substituted dihydroronaphthalenes
  作者：A.I. Meyers、Jack D. Brown、Dominique Laucher

  DOI：10.1016/s0040-4039(00)96707-8

  日期：1987.1