2-n-Propyl-1,4-pentadiene | 32852-38-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-n-Propyl-1,4-pentadiene
• 英文别名: 2-propyl-1,4-pentadiene；2-propyl-penta-1,4-diene；4-Methylidenehept-1-ene
• CAS: 32852-38-3
• 化学式: C₈H₁₄
• 分子量: 110.199
• InChiKey: QZLIBACUUHYHAH-UHFFFAOYSA-N

物化性质

• 沸点：
  115-116 °C
• 密度：
  0.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-n-Propyl-1,4-pentadiene 、 三甲基溴化锡 在 BuLi/BuOK 作用下， 以 not given 为溶剂， 以0%的产率得到
  参考文献：
  名称：

  锡亲电试剂对戊二烯阴离子的区域和立体选择性捕获

  摘要：

  无论阴离子的结构如何，带有甲氧基甲基的戊二烯基阴离子与 Me3SnBr 的亲电捕获均以高区域选择性得到 Z-戊二烯基锡烷。

  DOI：

  10.1246/cl.1988.135
• 作为产物：
  描述：

  戊酸甲酯 在 吡啶 、 lithium aluminium tetrahydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 2-n-Propyl-1,4-pentadiene
  参考文献：
  名称：

  Highly selective trapping of unsymmetrical pentadienyl anions by silicon and tin electrophiles. Marked contrast between kinetic and thermodynamic control of product composition

  摘要：

  The nucleophilic reaction of lithium and potassium salts of five pentadienyl anions bearing sterically and/or coordinatively different groups at their unsymmetrical 2-position toward Me3SiCl and Me3SnBr is described. When the anion of the potassium salt was trapped by Me3SiCl, (Z)-4-substituted-pentadienylsilanes were obtained with high selectivity (87-100%). The lithium salt, however, gave a mixture of (E)- and (Z)-4-substituted-pentadienylsilanes. The coupling reaction proceeds under kinetic control, because the product composition from Si trapping reflected the structure of the parent dienyl anion and the steric interaction between the incoming Me3Si group and the substituent on the anion. In contrast, when the anion was trapped by Me3SnBr under the identical conditions, (Z)-2-substituted-pentadienyltins were formed with 60-96% selectivity. Only relatively small changes in product composition, as a function of the cation or the substituent on the anion, were observed. These results could be explained by thermodynamic controlling factors, including a 1,5-Me3Sn shift, and a redistribution of pentadienyl groups under basic conditions.

  DOI：

  10.1021/jo00006a011

文献信息

• A Convenient Method for the Generation of Allylic Dihaloboranes and Diallyl(chloro)borane and Their Application in the Allylboration of Alkenes and Acetylenes
  作者：Yuri N. Bubnov、Nikolai Y. Kuznetsov、Fedor V. Pastukhov、Vadim V. Kublitsky

  DOI：10.1002/ejoc.200500391

  日期：2005.11

  products were isolated by standard techniques and transformed into boronates (boron amides). Deboronation of these products led to 1,4-pentadiene derivatives or unsaturated alcohols. 2-Substituted 1,4-pentadienyl(dichloro)boranes obtained from acetylenes underwent intramolecular chloroboration at a moderate temperature to form 5-chloro-2-borinene derivatives. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451

  基于 BHal3（Hal = Cl，Br）和烯丙基三有机硼烷（烯丙基、肉桂基和 2-亚甲基环丁烷衍生物）之间的交换反应，开发了一种用于高反应性烯丙基二卤代硼烷和二烯丙基（氯）硼烷的便捷方法。由此产生的化合物容易与末端烯烃和乙炔反应形成相应的顺式-1,2-烯丙基硼化产物。这些产品通过标准技术分离并转化为硼酸盐（硼酰胺）。这些产品的脱硼产生 1,4-戊二烯衍生物或不饱和醇。从乙炔获得的 2-取代的 1,4-戊二烯基（二氯）硼烷在中等温度下进行分子内氯硼化反应，形成 5-氯-2-硼烯衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Direct one-pot synthesis of terminal olefins and deuterio olefins from carboxylic acid chlorides
  作者：Jose Barluenga、Miguel Yus、Jose M. Concellon、Pablo Bernad

  DOI：10.1021/jo00166a041

  日期：1983.9
• Miginiac,L.; Lanoiselee,M., Bulletin de la Societe Chimique de France, 1971, p. 2716 - 2720
  作者：Miginiac,L.、Lanoiselee,M.

  DOI：——

  日期：——
• Curry, Michael J.; Stevens, D.R., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1756 - 1760
  作者：Curry, Michael J.、Stevens, D.R.

  DOI：——

  日期：——
• CURRY M. J.; STEVENS I. D. R., J. CHEM. SOC. PERKIN TRANS., 1980, PART 1, NO 8, 1756-1760
  作者：CURRY M. J.、 STEVENS I. D. R.

  DOI：——

  日期：——