(9R,10R)-2,6-diphenyl-3,4,7,8,9,10-hexahydro-1,5-naphthyridine | 425603-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (9R,10R)-2,6-diphenyl-3,4,7,8,9,10-hexahydro-1,5-naphthyridine
• 英文别名: (4aR,8aR)-2,6-diphenyl-3,4,4a,7,8,8a-hexahydro-1,5-naphthyridine
• CAS: 425603-28-7
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: VPYXGDBYASIFIM-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9R,10R)-2,6-diphenyl-3,4,7,8,9,10-hexahydro-1,5-naphthyridine 在 5percent Rh/Al₂O₃ 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 48.0h， 以0.180 g的产率得到(2R,6R,9R,10R)-2,6-diphenyl-1,5-diaza-cis-decalin
  参考文献：
  名称：

  Conformational Control of Flexible Molecules:  Design and Synthesis of Novel Chiral 1,5-Diaza-cis-decalins

  摘要：

  Control of the conformational equilibria of 1,5-diaza-cis-decalins, a new class of chiral diamine ligands, has been investigated. Chiral 2,6- and 3,7-substituted derivatives of 1,5-diaza-cis-decalins were designed to stabilize the conformational form needed to chelate a lithium. These derivatives were synthesized in optically pure form starting from 1,5-diaza-cis-decalin. Due to the rigid and conformationally well-defined nature of these compounds, the potential of these compounds as chiral diamine ligands was investigated. Asymmetric lithiation-substitution reactions of N-Boc-pyrrolidine and N,N-diisopropyl-o-ethylbenzamide were performed using these ligands and up to 60% ee was obtained. For the latter substrate, results spanning a range from 32% ee (R) to 60% ee (S) were obtained (Deltaee = 92%) with 1,5-diaza-cis-decalin ligands differing only in the location of two methyl substituents. Unlike many other diamines that have been employed in asymmetric lithiation-substitution reactions, the limited conformational flexibility of the 1,5-diaza-cis-decalins is analogous to (-)-sparteine such that these results may permit the construction of structure-activity relationships.

  DOI：

  10.1021/jo025503x
• 作为产物：
  描述：

  ditert-butyl (4aR,8aR)-2,6-bis(trifluoromethylsulfonyloxy)-4,4a,8,8a-tetrahydro-1,5-naphthyridine-1,5-dicarboxylate 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.5h， 生成 (9R,10R)-2,6-diphenyl-3,4,7,8,9,10-hexahydro-1,5-naphthyridine
  参考文献：
  名称：

  Conformational Control of Flexible Molecules:  Design and Synthesis of Novel Chiral 1,5-Diaza-cis-decalins

  摘要：

  Control of the conformational equilibria of 1,5-diaza-cis-decalins, a new class of chiral diamine ligands, has been investigated. Chiral 2,6- and 3,7-substituted derivatives of 1,5-diaza-cis-decalins were designed to stabilize the conformational form needed to chelate a lithium. These derivatives were synthesized in optically pure form starting from 1,5-diaza-cis-decalin. Due to the rigid and conformationally well-defined nature of these compounds, the potential of these compounds as chiral diamine ligands was investigated. Asymmetric lithiation-substitution reactions of N-Boc-pyrrolidine and N,N-diisopropyl-o-ethylbenzamide were performed using these ligands and up to 60% ee was obtained. For the latter substrate, results spanning a range from 32% ee (R) to 60% ee (S) were obtained (Deltaee = 92%) with 1,5-diaza-cis-decalin ligands differing only in the location of two methyl substituents. Unlike many other diamines that have been employed in asymmetric lithiation-substitution reactions, the limited conformational flexibility of the 1,5-diaza-cis-decalins is analogous to (-)-sparteine such that these results may permit the construction of structure-activity relationships.

  DOI：

  10.1021/jo025503x

文献信息

• Conformational Control of Flexible Molecules:  Design and Synthesis of Novel Chiral 1,5-Diaza-<i>cis</i>-decalins
  作者：Zhenrong Xu、Marisa C. Kozlowski

  DOI：10.1021/jo025503x

  日期：2002.5.1

  Control of the conformational equilibria of 1,5-diaza-cis-decalins, a new class of chiral diamine ligands, has been investigated. Chiral 2,6- and 3,7-substituted derivatives of 1,5-diaza-cis-decalins were designed to stabilize the conformational form needed to chelate a lithium. These derivatives were synthesized in optically pure form starting from 1,5-diaza-cis-decalin. Due to the rigid and conformationally well-defined nature of these compounds, the potential of these compounds as chiral diamine ligands was investigated. Asymmetric lithiation-substitution reactions of N-Boc-pyrrolidine and N,N-diisopropyl-o-ethylbenzamide were performed using these ligands and up to 60% ee was obtained. For the latter substrate, results spanning a range from 32% ee (R) to 60% ee (S) were obtained (Deltaee = 92%) with 1,5-diaza-cis-decalin ligands differing only in the location of two methyl substituents. Unlike many other diamines that have been employed in asymmetric lithiation-substitution reactions, the limited conformational flexibility of the 1,5-diaza-cis-decalins is analogous to (-)-sparteine such that these results may permit the construction of structure-activity relationships.