(3R,7R,9R,10R)-3,7-dimethyl-1,5-diaza-cis-decalin | 425603-32-3

• 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: (3R,7R,9R,10R)-3,7-dimethyl-1,5-diaza-cis-decalin
• 英文别名: (3R,4aR,7R,8aR)-3,7-dimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,5-naphthyridine
• CAS: 425603-32-3
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: ARVGKMYAGWLEQN-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (3R,7R,9R,10R)-3,7-dimethyl-1,5-diaza-cis-decalin 在 甲酸 作用下， 以 水 为溶剂， 反应 36.0h， 以82%的产率得到(3R,7R,9R,10R)-1,3,5,7-tetramethyl-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：

  (9R,10R)-N,N'-di-tert-butoxycarbonyl-2,6-dioxo-1,5-diaza-cis-decalin 在 lithium aluminium tetrahydride 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 75.5h， 生成 (3R,7R,9R,10R)-3,7-dimethyl-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

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.