2,2-dimethylhexadecanenitrile | 903502-55-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-dimethylhexadecanenitrile
• 英文别名: 2,2-dimethylhexadecannitrile
• CAS: 903502-55-6
• 化学式: C₁₈H₃₅N
• 分子量: 265.483
• InChiKey: KFOURKVVNXADFB-UHFFFAOYSA-N

物化性质

• 熔点：
  27 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  354.7±10.0 °C(Predicted)
• 密度：
  0.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  2,2-dimethylhexadecanenitrile 在 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 3,3-dimethylheptadec-1-ene
  参考文献：
  名称：

  Total Synthesis and Structural Verification of Some Novel Branched Alkanes with Quaternary Carbons Isolated from Diverse Geological Sources

  摘要：

  With a view to the authentication of an unusual series of branched alkanes with quaternary centers (BAQCs) isolated from geological samples, and whose structures rest on the interpretation of EI-mass spectral fragmentation patterns, the total synthesis of 3-ethyl-3-methylheptadecane, 3,3-dimethylheptadecane, 3,3,11,11-tetraethyltridecane, and 5,5,7,7-tetraethylundecane is described. The GC-MS data of the first two samples are identical with those of the isolates and confirm their structures. However, the GC-MS data of the two more highly branched structures do not match those of the geological isolates leading to the conclusion that these structures were erroneously assigned.

  DOI：

  10.1021/jo0603983
• 作为产物：
  描述：

  异丁腈 、 溴代十四烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以76%的产率得到2,2-dimethylhexadecanenitrile
  参考文献：
  名称：

  突破中性有机电子给体的极限：四（亚氨基正膦酸酯）取代的双吡啶亚次甲基

  摘要：

  制备了一种新的基态有机电子给体，其在双吡啶亚烷基骨架上具有四个强烈的π-供电子亚氨基膦酸酯取代基。循环伏安法显示，该对夫妇涉及中性有机供体及其指示，相对于饱和甘汞电极（SCE），记录的氧化还原电势为-1.70V。可以通过涉及易于制备的吡啶鎓离子前体的去质子化反应来分离（44％）这种高还原性有机化合物，或者更方便地就地生成。该给体能够还原各种芳基卤化物，并且由于其氧化还原电位，被发现是第一个对热诱导的N，N还原SN键裂解有效的有机给体。-二烷基磺酰胺和丙二醛的还原性加氢脱氰作用。

  DOI：

  10.1002/anie.201505378

文献信息

• Differentiating CBr and CCl Bond Activation by Using Solvent Polarity: Applications to Orthogonal Alkyl-Alkyl Negishi Reactions
  作者：Niloufar Hadei、George T. Achonduh、Cory Valente、Christopher J. O'Brien、Michael G. Organ

  DOI：10.1002/anie.201100705

  日期：2011.4.18

  A pot to share: A CalkylCl bond can be rendered “dormant” or “active” in the Negishi alkyl–alkyl cross‐coupling by a simple solvent polarity “switch” (see scheme). Adjustment from a 1:2 to a 2:1 solvent ratio of dimethylimidazolidinone:tetrahydrofuran enables orthogonal alkyl–alkyl Negishi cross‐coupling strategies to be carried out on bifunctional bromochloroalkanes in one pot at room temperature

  一个共享的锅：通过简单的溶剂极性“转换”，在Negishi烷基-烷基交叉偶联中，AC烷基Cl键可被“休眠”或“激活”。将二甲基咪唑啉酮：四氢呋喃的溶剂比例从1：2调整为2：1，可以在室温下在一锅中对双官能溴氯烷烃进行正交烷基-烷基Negishi交叉偶联策略。
• Pushing the Limits of Neutral Organic Electron Donors: A Tetra(iminophosphorano)-Substituted Bispyridinylidene
  作者：Samuel S. Hanson、Eswararao Doni、Kyle T. Traboulsee、Graeme Coulthard、John A. Murphy、C. Adam Dyker

  DOI：10.1002/anie.201505378

  日期：2015.9.14

  deprotonation reaction involving its readily prepared pyridinium ion precursor. This donor is able to reduce a variety of aryl halides, and, owing to its redox potential, was found to be the first organic donor to be effective in the thermally induced reductive SN bond cleavage of N,N‐dialkylsulfonamides, and reductive hydrodecyanation of malonitriles.

  制备了一种新的基态有机电子给体，其在双吡啶亚烷基骨架上具有四个强烈的π-供电子亚氨基膦酸酯取代基。循环伏安法显示，该对夫妇涉及中性有机供体及其指示，相对于饱和甘汞电极（SCE），记录的氧化还原电势为-1.70V。可以通过涉及易于制备的吡啶鎓离子前体的去质子化反应来分离（44％）这种高还原性有机化合物，或者更方便地就地生成。该给体能够还原各种芳基卤化物，并且由于其氧化还原电位，被发现是第一个对热诱导的N，N还原SN键裂解有效的有机给体。-二烷基磺酰胺和丙二醛的还原性加氢脱氰作用。
• Total Synthesis and Structural Verification of Some Novel Branched Alkanes with Quaternary Carbons Isolated from Diverse Geological Sources
  作者：David Crich、Huadong Xu、Fabien Kenig

  DOI：10.1021/jo0603983

  日期：2006.6.1

  With a view to the authentication of an unusual series of branched alkanes with quaternary centers (BAQCs) isolated from geological samples, and whose structures rest on the interpretation of EI-mass spectral fragmentation patterns, the total synthesis of 3-ethyl-3-methylheptadecane, 3,3-dimethylheptadecane, 3,3,11,11-tetraethyltridecane, and 5,5,7,7-tetraethylundecane is described. The GC-MS data of the first two samples are identical with those of the isolates and confirm their structures. However, the GC-MS data of the two more highly branched structures do not match those of the geological isolates leading to the conclusion that these structures were erroneously assigned.