(1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-ethyl-1,2-dihydronaphthalene | 138234-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-ethyl-1,2-dihydronaphthalene
• 英文别名: [(1R,2S)-2-ethyl-1,2-dihydronaphthalen-1-yl]methanol
• CAS: 138234-69-2
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: QIOPAQSTDQLKMK-GXFFZTMASA-N

物化性质

• 沸点：
  308.3±11.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-ethyl-1,2-dihydronaphthalene 在 吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (1R,2S)-trans-1-(cyanomethyl)-2-ethyl-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
• 作为产物：
  描述：

  (4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-ethyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines

  摘要：

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.

  DOI：

  10.1021/jo00030a035

文献信息

• A novel asymmetric synthesis of 3-benzyl-1,2,3,4,5,6-hexahydro-11-alkyl-2,6-methano-3-benzazocines
  作者：Xu Bai、S. Wayne Mascarella、Wayne D. Bowen、F. Ivy Carroll

  DOI：10.1039/c39940002401

  日期：——

  9-Alkyl 6,7-benzomorphans (1,2,3,4,5,6-hexahydro-11-alkyl-2,6-methano-3-benzazocines) are important selective ligands of sigma receptor sites; their asymmetric synthesis starting with (1R, 2R)- or (1S, 2S)-1-hydroxymethyl-2-alkyl-2-alkyl-1,2-dihydronaphthalene is described.

  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。
• 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.
• 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines
  作者：Lendon N. Pridgen、Mohamed K. Mokhallalati、Ming Jung Wu

  DOI：10.1021/jo00030a035

  日期：1992.2

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.