7,7-dimethyloctanenitrile | 1402161-04-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 7,7-dimethyloctanenitrile
• CAS: 1402161-04-9
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: JLKXXFZFFOAOBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7,7-dimethyloctanenitrile 在 双氧水 、 溶剂黄146 、 C₄₆H₄₀F₁₈MnN₆O₆S₂ 作用下， 以33 %的产率得到
  参考文献：
  名称：

  10.1002/anie.202402858

  摘要：

  AbstractThe tert‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic and organometallic molecules. Because of the combination of a high bond dissociation energy (~100 kcal mol−1) and limited accessibility, in the absence of directing groups, neither radical nor organometallic approaches are effective for the chemical modification of tert‐butyl C−H bonds. Herein we overcome these limits by employing a highly electrophilic manganese catalyst, [Mn(CF3bpeb)(OTf)2], that operates in the strong hydrogen bond donor solvent nonafluoro‐tert‐butyl alcohol (NFTBA) and catalytically activates hydrogen peroxide to generate a powerful manganese‐oxo species that effectively oxidizes tert‐butyl C−H bonds. Leveraging on the interplay of steric, electronic, medium and torsional effects, site‐selective and product chemoselective hydroxylation of the tert‐butyl group is accomplished with broad reaction scope, delivering primary alcohols as largely dominant products in preparative yields. Late‐stage hydroxylation at tert‐butyl sites is demonstrated on 6 densely functionalized molecules of pharmaceutical interest. This work uncovers a novel disconnection approach, harnessing tert‐butyl as a potential functional group in strategic synthetic planning for complex molecular architectures.

  DOI：

  10.1002/anie.202402858
• 作为产物：
  描述：

  6-溴己腈 、 叔丁基氯化镁 在 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到7,7-dimethyloctanenitrile
  参考文献：
  名称：

  铜催化的官能化卤代烃和甲苯磺酸盐与仲烷基和叔烷基格氏试剂的偶联

  摘要：

  附加值：铜基方法对于烷基亲电试剂与仲烷基和叔烷基格氏试剂的交叉偶联非常有效。该方法以其广泛的底物范围和高官能团耐受性而著称。

  DOI：

  10.1002/anie.201204275

文献信息

• Novel Bicyclic Cannabinoids
  申请人：Makriyannis Alexandros

  公开号：US20070135388A1

  公开（公告）日：2007-06-14

  Bicyclic-cannabinoids and methods of preparation and use are presented. These compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本文介绍了双环大麻素及其制备和使用方法。当以治疗有效量的这些化合物给个体或动物注射时，会在个体或动物体内产生足够高的该化合物水平，从而引起生理反应。这种生理反应可能对治疗多种生理状况有用。
• US7446229B2
  申请人：——

  公开号：US7446229B2

  公开（公告）日：2008-11-04