(9R,10R)-N,N'-di-tert-butoxycarbonyl-1,5-diaza-cis-decalin | 355131-80-5

• 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)-N,N'-di-tert-butoxycarbonyl-1,5-diaza-cis-decalin
• 英文别名: ditert-butyl (4aR,8aR)-2,3,4,4a,6,7,8,8a-octahydro-1,5-naphthyridine-1,5-dicarboxylate
• CAS: 355131-80-5
• 化学式: C₁₈H₃₂N₂O₄
• 分子量: 340.463
• InChiKey: SMLOMCUIRVWVKD-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9R,10R)-N,N'-di-tert-butoxycarbonyl-1,5-diaza-cis-decalin 在 Rh/Al₂O₃ ruthenium(IV) oxide 、 二氯二茂钛 、 sodium periodate 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， -15.0~80.0 ℃ 、1.1 MPa 条件下， 反应 98.0h， 生成 (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
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (R,R)-cis-decahydro-1,5-naphthyridine (R,R)-tartrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以94%的产率得到(9R,10R)-N,N'-di-tert-butoxycarbonyl-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.
• 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.