2-methylocta-5(E),7-dienenitrile | 569329-41-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-methylocta-5(E),7-dienenitrile
• 英文别名: 2-methylocta-5,7-dienenitrile；(5E)-2-methylocta-5,7-dienenitrile
• CAS: 569329-41-5
• 化学式: C₉H₁₃N
• 分子量: 135.209
• InChiKey: JSFQHORADMGBJU-SNAWJCMRSA-N

物化性质

• 沸点：
  222.8±19.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 作为反应物：
  描述：

  2-methylocta-5(E),7-dienenitrile 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 甲苯 、 苯 为溶剂， 反应 1.0h， 生成 (3R,3aS,9R,9aR)-6-Methoxy-3-methyl-9-vinyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinoline
  参考文献：
  名称：

  Efficient Construction of Cyclopenta[b]quinoline Core of Isoschizozygane Alkaloids via Intramolecular Formal Hetero-Diels−Alder Reaction

  摘要：

  [GRAPHICS]Acid-catalyzed condensation of aromatic amines with delta,epsilon-unsaturated aldehydes, followed by intramolecular formal hetero Diels-Alder reaction, is described as a potential route to the cyclopenta[b]quinoline substructure of isoschizozygane alkaloids. Reactions are highly diastereoselective and produce adducts with up to four contiguous stereocenters.

  DOI：

  10.1021/ol034776r
• 作为产物：
  描述：

  (E)-6-bromohexa-1,3-diene 、 丙腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到2-methylocta-5(E),7-dienenitrile
  参考文献：
  名称：

  Efficient Construction of Cyclopenta[b]quinoline Core of Isoschizozygane Alkaloids via Intramolecular Formal Hetero-Diels−Alder Reaction

  摘要：

  [GRAPHICS]Acid-catalyzed condensation of aromatic amines with delta,epsilon-unsaturated aldehydes, followed by intramolecular formal hetero Diels-Alder reaction, is described as a potential route to the cyclopenta[b]quinoline substructure of isoschizozygane alkaloids. Reactions are highly diastereoselective and produce adducts with up to four contiguous stereocenters.

  DOI：

  10.1021/ol034776r

文献信息

• Intramolecular Hydroamination/Cyclization of Conjugated Aminodienes Catalyzed by Organolanthanide Complexes. Scope, Diastereo- and Enantioselectivity, and Reaction Mechanism
  作者：Sukwon Hong、Amber M. Kawaoka、Tobin J. Marks

  DOI：10.1021/ja036266y

  日期：2003.12.1

  precatalysts for the rapid, regioselective, and highly diastereoselective intramolecular hydroamination/cyclization of primary and secondary amines tethered to conjugated dienes. The rates of aminodiene cyclizations are significantly more rapid than those of the corresponding aminoalkenes. This dienyl group rate enhancement as well as substituent group (R) effects on turnover frequencies is consistent with

  一般类型的有机镧系元素配合物 Cp'(2)LnCH(TMS)(2) (Cp' = eta(5)-Me(5)C(5); Ln = La, Sm, Y; TMS = SiMe(3) ) 和 CGCSmN(TMS)(2) (CGC = Me(2)Si(eta(5)-Me(4)C(5))((t)()BuN)) 作为快速、区域选择性的有效预催化剂，以及与共轭二烯相连的伯胺和仲胺的高度非对映选择性分子内加氢胺化/环化。氨基二烯环化的速度明显快于相应的氨基烯烃。这种二烯基速率增强以及取代基 (R) 对转换频率的影响与提议的过渡态电子需求一致。动力学和机械数据平行单取代氨基烯烃加氢胺化/环化，转换限制 C=C 插入 Ln-N 键，可能形成 Ln-eta(3) 烯丙基中间体，然后快速质子分解所得 Ln-C 键。速率定律在[催化剂]中是一级的，在[氨基二烯]中是零级的。然而，根据特定的底物和催化剂组合，与零级
• Efficient Construction of Cyclopenta[<i>b</i>]quinoline Core of Isoschizozygane Alkaloids via Intramolecular Formal Hetero-Diels−Alder Reaction
  作者：Nabi A. Magomedov

  DOI：10.1021/ol034776r

  日期：2003.7.1

  [GRAPHICS]Acid-catalyzed condensation of aromatic amines with delta,epsilon-unsaturated aldehydes, followed by intramolecular formal hetero Diels-Alder reaction, is described as a potential route to the cyclopenta[b]quinoline substructure of isoschizozygane alkaloids. Reactions are highly diastereoselective and produce adducts with up to four contiguous stereocenters.