(2Z,4E)-nona-2,4-dienenitrile | 53378-99-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2Z,4E)-nona-2,4-dienenitrile
• 英文别名: 2(Z),4(E)-Nonadiennitril
• CAS: 53378-99-7
• 化学式: C₉H₁₃N
• 分子量: 135.209
• InChiKey: KNKLDSOWHQCJAH-MDAAKZFYSA-N

物化性质

• 沸点：
  227.5±9.0 °C(Predicted)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-己炔 在 palladium diacetate 氧气 、 sodium carbonate 、 儿萘酚硼烷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 8.0h， 生成 (2Z,4E)-nona-2,4-dienenitrile
  参考文献：
  名称：

  Oxygen-Promoted Palladium(II) Catalysis:  Facile C(sp²)−C(sp²) Bond Formation via Cross-Coupling of Alkenylboronic Compounds and Olefins

  摘要：

  Oxygen-promoted Pd(II) catalysis facilitated the synthesis of conjugated dienes; by cross-coupling of alkenylboronic compounds and various olefins including highly substituted alkenes and cyclohexenone. Under mild conditions, these versatile reactions were efficient and highly stereoselective.

  DOI：

  10.1021/ol0483192

文献信息

• Oxidative Palladium(II) Catalysis:  A Highly Efficient and Chemoselective Cross-Coupling Method for Carbon−Carbon Bond Formation under Base-Free and Nitrogenous-Ligand Conditions
  作者：Kyung Soo Yoo、Cheol Hwan Yoon、Kyung Woon Jung

  DOI：10.1021/ja063710z

  日期：2006.12.1

  For instance, oxidative palladium(II) catalysis is effective with highly substituted alkenes and cyclic alkenes, which are known to be incompatible with other known catalytic conditions. Most examined reactions progressed smoothly to completion at low temperatures and in short times. These interesting results provide mechanistic insights and utilities for a new paradigm of palladium catalytic cycles

  我们在此报告了氧促进 Pd(II) 催化的通用和温和协议的开发，导致烯基和芳基硼化合物与各种烯烃的选择性交叉偶联。与大多数交叉偶联反应不同，这种新方法即使在没有碱基的情况下也能很好地工作，因此避免了不需要的同源偶联。包括二甲基菲咯啉在内的基于氮的配体增强了反应性，并提供了一种高效的立体选择性方法来克服具有挑战性的底物限制。例如，氧化钯 (II) 催化对于高度取代的烯烃和环烯烃是有效的，已知它们与其他已知的催化条件不相容。大多数检查的反应在低温和短时间内顺利完成。
• Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
  作者：Johannes H. Harenberg、Niels Weidmann、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.202012085

  日期：2021.1.11

  The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe2 or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized

  使用 EtNMe 2中的 NaDA（二异丙基酰胺钠）或正己烷中的 NaTMP（2,2,6,6-四甲基哌啶钠）·TMEDA 在连续流装置中对取代的丙烯腈和烯基硫醚进行钠化，得到钠化的丙烯腈和烯基硫醚，随后与各种亲电子试剂（例如醛、酮、二硫化物和烯丙基溴）分批捕获，得到官能化的丙烯腈和烯基硫醚。通过使用巴比耶型条件，该流程已成功扩展到其他丙烯酸酯。
• Reaction of trialkylboranes with 2-bromo-6-lithiopyridine
  作者：K. Utimoto、N. Sakai、M. Obayashi、H. Nozaki

  DOI：10.1016/0040-4020(76)80002-6

  日期：1976.1

  Reaction of 2-bromo-6-lithiopyridine with trialkylboranes affords 5-alkyl-5-dialkylboryl-2-(Z), 4(E)- pentadienenitriles by stereospecific alkylative cleavage of the pyridine ring. These intermediary vinylboranes are versatile reagents for the preparation of 5-alkyl-2(Z), 4(E)-pentadienenitriles, 5,5-dialkyl-4-pentenenitriles and 5,5-dialkyl-2,4-pentadienenitriles.

  2-溴-6-硫代吡啶与三烷基硼烷的反应通过吡啶环的立体定向烷基化裂解得到5-烷基-5-二烷基硼基-2-（Z），4（E）-戊二烯腈。这些中间体乙烯基硼烷是用于制备5-烷基-2（Z），4（E）-戊二烯腈，5,5-二烷基-4-戊烯腈和5,5-二烷基-2,4-戊二烯腈的通用试剂。
• Oxygen-Promoted Palladium(II) Catalysis:  Facile C(sp²)−C(sp²) Bond Formation via Cross-Coupling of Alkenylboronic Compounds and Olefins
  作者：Cheol Hwan Yoon、Kyung Soo Yoo、Sung Wook Yi、Rajesh K. Mishra、Kyung Woon Jung

  DOI：10.1021/ol0483192

  日期：2004.10.1

  Oxygen-promoted Pd(II) catalysis facilitated the synthesis of conjugated dienes; by cross-coupling of alkenylboronic compounds and various olefins including highly substituted alkenes and cyclohexenone. Under mild conditions, these versatile reactions were efficient and highly stereoselective.