(2S,6S,9R,10R)-2,6-dimethyl-1,5-diaza-cis-decalin | 355131-86-1

• 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: (2S,6S,9R,10R)-2,6-dimethyl-1,5-diaza-cis-decalin
• 英文别名: 2,6-dimethyldecahydro-1,5-naphthyridine；2,6-dimethyl-1,5-diaza-cis-decalin；(2S,4aR,6S,8aR)-2,6-dimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,5-naphthyridine
• CAS: 355131-86-1
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: LQPIKJMBUZADGZ-AXTSPUMRSA-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 、 (2S,6S,9R,10R)-2,6-dimethyl-1,5-diaza-cis-decalin 在 甲酸 作用下， 以 水 为溶剂， 反应 41.0h， 以60%的产率得到(2S,6S,9R,10R)-1,2,5,6-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)-2,6-dimethyl-3,4,7,8,9,10-hexahydro-1,5-naphthyridine 在 Rh/Al₂O₃ 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 20.0 ℃ 、1.1 MPa 条件下， 反应 36.0h， 以0.380 g的产率得到(2S,6S,9R,10R)-2,6-dimethyl-1,5-diaza-cis-decalin
  参考文献：
  名称：

  Synthesis and conformational analysis of 2,6-dimethyl-1,5-diaza-cis-decalins

  摘要：

  The stereoselective synthesis of 2,6-dimethyl-1,5-diaza-cis-decalins with the dimethyl groups syn or anti to the angular hydrogens has been accomplished starting from 1,5-diaza-cis-decalin. From an NMR study of the conformational properties of all three 2,6-dimethyl-1,5-diaza-cis-decalins, the components which affect the conformational equilibrium have been identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00370-2

文献信息

• Asymmetric Ruthenium-Catalyzed Hydrogenation of 2,6-Disubstituted 1,5-Naphthyridines: Access to Chiral 1,5-Diaza-<i>cis</i>-Decalins
  作者：Jianwei Zhang、Fei Chen、Yan-Mei He、Qing-Hua Fan

  DOI：10.1002/anie.201411105

  日期：2015.4.7

  developed. A wide range of 1,5‐naphthyridine derivatives were efficiently hydrogenated to give 1,2,3,4‐tetrahydro‐1,5‐naphthyridines with up to 99 % ee and full conversions. This facile and green protocol is applicable to the scaled‐up synthesis of optically pure 1,5‐diaza‐cis‐decalins, which have been used as rigid chelating diamine ligands for asymmetric synthesis.

  已经开发了由手性阳离子钌二胺络合物催化的2,6-二取代和2,3,6-三取代的1,5-萘啶的不对称氢化（AH）。各种1,5-萘啶衍生物均被有效氢化，得到1,2,3,4-四氢-1,5-萘啶类化合物，ee最高可达99％， 并且可以完全转化。该简便而绿色的方案适用于光学纯的1,5-二氮杂顺式十氢化萘的放大合成，该合成已用作不对称合成的刚性螯合二胺配体。
• Homogeneous Perdehydrogenation and Perhydrogenation of Fused Bicyclic N-Heterocycles Catalyzed by Iridium Complexes Bearing a Functional Bipyridonate Ligand
  作者：Ken-ichi Fujita、Yui Tanaka、Masato Kobayashi、Ryohei Yamaguchi

  DOI：10.1021/ja5001888

  日期：2014.4.2

  Homogeneous perdehydrogenation of saturated bicyclic 2,6-dimethyldecahydro-1,5-naphthyridine and perhydrogenation of aromatic 2,6-dimethyl-1,5-naphthyridine with release and uptake of five molecules of H-2 are efficiently achieved by iridium complexes bearing a functional bipyridonate ligand. Successive perhydrogenation and perdehydrogenation of 2,6-dimethyl-1,5-naphthryridine using a single iridium complex also proceed with the reversible inter-conversion of the catalytic species, depending on the presence or absence of H-2.
• 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.
• Synthesis and conformational analysis of 2,6-dimethyl-1,5-diaza-cis-decalins
  作者：Marisa C. Kozlowski、Zhenrong Xu、A.Gil Santos

  DOI：10.1016/s0040-4020(01)00370-2

  日期：2001.5

  The stereoselective synthesis of 2,6-dimethyl-1,5-diaza-cis-decalins with the dimethyl groups syn or anti to the angular hydrogens has been accomplished starting from 1,5-diaza-cis-decalin. From an NMR study of the conformational properties of all three 2,6-dimethyl-1,5-diaza-cis-decalins, the components which affect the conformational equilibrium have been identified. (C) 2001 Elsevier Science Ltd. All rights reserved.