3,7-diisopropyl-3,7-diazabicyclo[3.3.1]nonane-9-one | 173973-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,7-diisopropyl-3,7-diazabicyclo[3.3.1]nonane-9-one
• 英文别名: 3,7-di-i-propyl-3,7-diazabicyclo[3.3.1]nonan-9-one；3,7-diisopropyl-3,7-diazabicyclo[3.3.1]nonan-9-one；3,7-di(propan-2-yl)-3,7-diazabicyclo[3.3.1]nonan-9-one
• CAS: 173973-33-6
• 化学式: C₁₃H₂₄N₂O
• 分子量: 224.346
• InChiKey: YGTKXITWJVCHQV-UHFFFAOYSA-N

物化性质

• 沸点：
  112°/0.2mm
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3,7-diisopropyl-3,7-diazabicyclo[3.3.1]nonane-9-one 在 一水合肼 、 potassium hydroxide 作用下， 以 二乙二醇 为溶剂， 反应 16.0h， 以88%的产率得到3,7-di-i-propyl-3,7-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  在 N-boc 吡咯烷的双配体催化不对称去质子化中作为化学计量配体的双吡啶研究

  摘要：

  已经合成并评估了一系列非手性双吡啶作为 N-Boc 吡咯烷的双配体催化不对称去质子化中的化学计量配体。

  DOI：

  10.3998/ark.5550190.0012.519
• 作为产物：
  描述：

  1-异丙基-4-哌啶酮 、 异丙胺 在 盐酸 、 paraformaldehyde 作用下， 以 甲醇 、 N2 、 溶剂黄146 为溶剂， 生成 3,7-diisopropyl-3,7-diazabicyclo[3.3.1]nonane-9-one
  参考文献：
  名称：

  N-alkyl and n-acyl derivatives of 3,7-diazabicyclo-[3.3.1]nonanes and

  摘要：

  3,7-二氮杂双环[3.3.1]壬烷及其选择性衍生物的一般公式如下：##STR1## 被披露为多类抗心律失常药物。

  公开号：

  US05468858A1

文献信息

• Regioselective Lithiation of Silyl Phosphine Sulfides: Asymmetric Synthesis of <i>P</i>-Stereogenic Compounds
  作者：Jonathan J. Gammon、Peter O’Brien、Brian Kelly

  DOI：10.1021/ol901977p

  日期：2009.11.5

  lithiation of a dimethylphosphine sulfide), a two-step process of regioselective lithiation-trapping and silyl group removal has been used to prepare a range of P-stereogenic compounds, including precursors to diphosphine ligands (e.g., Mini-PHOS). This two-step protocol delivers products with the opposite configuration to that obtained by direct asymmetric lithiation−trapping of a dimethylphosphine sulfide

  从99：1 er的三甲基甲硅烷基取代的磷化氢硫化物（由n -BuLi /（-）-天冬氨酸介导的二甲基膦硫化物的不对称锂化反应生成）开始，分两步进行区域选择性锂化捕获和甲硅烷基去除被用于制备一系列P -stereogenic化合物，包括前体二膦配体（例如，微型-PHOS）。此两步协议可提供与使用n -BuLi /（-）-partaine进行二甲基膦硫化物直接不对称锂化-阱化所获得的产品具有相反配置的产品。
• Development of a Catalytic Asymmetric Variant of Hoppe’s <i>O</i>-Alkyl Carbamate Deprotonation Methodology
  作者：Peter O’Brien、Matthew McGrath

  DOI：10.1055/s-2006-942417

  日期：2006.7

  The optimisation of a ligand-exchange approach to catalytic asymmetric deprotonation of O-alkyl carbamates and subsequent electrophilic trapping (the ‘Hoppe reaction’) is presented. The method uses s-BuLi and sub-stoichiometric amounts of a chiral diamine [(-)-sparteine or the (+)-sparteine surrogate] in conjunction with an achiral ‘regenerating’ diamine (bisisopropyl bispidine) for the deprotonation and proceeds with good yields (up to 84%) and high enantioselectivity (up to 94:6 er). The first applications of this catalytic asymmetric deprotonation methodology in natural product synthesis are also described.

  本文介绍了对催化 O-烷基氨基甲酸酯不对称去质子化及随后亲电捕集（"Hoppe 反应"）的配体交换方法的优化。该方法使用 s-BuLi、亚几何量的手性二胺[(-)-天冬氨酸或(+)-天冬氨酸代用品]以及非手性 "再生 "二胺（双异丙基双脒）进行去质子化反应，产率高（达 84%），对映选择性高（达 94:6er）。此外，还介绍了这种催化不对称去质子化方法在天然产物合成中的首次应用。
• N-alkyl and N-acyl derivatives of 3,7-Diazabicyclo-\x9b3.3.1!nonanes and
  申请人：The Board of Regents, Oklahoma State University

  公开号：US05786481A1

  公开（公告）日：1998-07-28

  3,7-Diazabicyclo\x9b3.3!nonanes and selected derivatives thereof of the general formula: ##STR1## wherein Q=S; Z=CH.sub.2 ; and Y equals an N-acyl or N-alkyl group are disclosed as multiclass antiarrhythmic agents.

  本文披露了3,7-二氮杂双环[3.3.0]庚烷及其选定衍生物的一般式：##STR1## 其中Q=S; Z=CH.sub.2 ; 且Y等于N-酰基或N-烷基基团，作为多类抗心律失常药物。
• Catalytic Asymmetric Deprotonation Using a Ligand Exchange Approach
  作者：Matthew J. McGrath、Peter O'Brien

  DOI：10.1021/ja056026d

  日期：2005.11.30

  A novel ligand exchange approach to catalytic asymmetric deprotonation-electrophilic trapping has been developed that uses 1.3 equiv of s-BuLi, 0.06-0.2 equiv of chiral diamine ((-)-sparteine or a (+)-sparteine surrogate), and 1.2 equiv of achiral bispidine. The methodology is illustrated with a range of examples and gives access to either enantiomer of useful chiral products in good yields using substoichiometric amounts of chiral diamines.
• Novel 3,7-Diheterabicyclo[3.3.1]nonanes That Possess Predominant Class III Antiarrhythmic Activity in 1-4 Day Post Infarction Dog Models:  X-ray Diffraction Analysis of 3-[4-(1<i>H</i>-Imidazol-1-yl)benzoyl]-7-isopropyl-3,7-diazabicyclo[3.3.1]nonane Dihydroperchlorate
  作者：Gregory L. Garrison、K. Darrell Berlin、Benjamin J. Scherlag、Ralph Lazzara、Eugene Patterson、Tamas Fazekas、Subbiah Sangiah、Chun-Lin Chen、F. D. Schubot、Dick van der Helm

  DOI：10.1021/jm950772j

  日期：1996.1.1

  Several 3,7-diheterabicyclo[3.3.1]nonanes (DHBCNs) were prepared and screened in the Harris dog model for their ability to abolish pace-induced and sustained ventricular tachycardia (SVT) or prevent induction of ventricular tachycardia. In addition, an electrophysiological examination was made in the infarcted hearts of each animal to determine if more than one class activity was present. The examples exhibited predominately class III antiarrhythmic activity via a prolongation of the ventricular effective refractory period (VERP) in the models, although there may well be an underlying class Ib action present as exemplified by the ability of several of the agents to slow conduction in the myocardial infarcted dog hearts. 3-[4-(1H-Imidazol-1-yl)benzoyl]-7-isopropyl-3,7-diazabicyclo[3.3.1]nonane dihydroperchlorate displayed powerful class III activity in the model systems while several other DHBCNs exhibited various degrees of class III action. An X-ray diffraction analysis revealed that this compound has a 3,7-diazabicyclo[3.3.1]nonane bicyclic unit in a chair-chair conformation.