1-Tetradecene, 4-methylene- | 87514-03-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-Tetradecene, 4-methylene-
• 英文别名: 4-methylidenetetradec-1-ene
• CAS: 87514-03-2
• 化学式: C₁₅H₂₈
• 分子量: 208.387
• InChiKey: OOVQAXHPKGASQY-UHFFFAOYSA-N

物化性质

• 沸点：
  267.5±10.0 °C(Predicted)
• 密度：
  0.783±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-allyl-1-dimethylphenylsilyl-1-dodecene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-Tetradecene, 4-methylene-
  参考文献：
  名称：

  用四丁基氟化铵裂解乙烯基碳-硅键

  摘要：

  用四丁基氟化铵从乙烯基碳上除去二甲基苯基甲硅烷基。硅原子上苯基的存在起着至关重要的作用。烯丙基二甲基甲硅烷基和烷氧基二甲基甲硅烷基的裂解也非常容易进行。

  DOI：

  10.1016/s0040-4020(01)96677-3

文献信息

• Tertiary Amine-Accelerated Allylgallation of Terminal Alkynes
  作者：Kazuhiko Takai、Yoshito Ikawa、Keijiro Ishii、Makoto Kumanda

  DOI：10.1246/cl.2002.172

  日期：2002.2

  Allylic gallium sesquibromides prepared by reduction of allylic bromides with gallium metal in the presence of a catalytic amount of indium, add to terminal alkynes with the aid of a tertiary amine to give 1,4-dienes.

  通过在催化量的铟存在下用金属镓还原烯丙基溴而制备的烯丙基倍半溴化镓，在叔胺的帮助下加到末端炔上，得到 1,4-二烯。
• Carbon–Carbon Bond Formation by Cross Coupling of Enol Phosphates or Enol Triflates with Organomanganese Compounds
  作者：Keigo Fugami、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/cl.1987.2203

  日期：1987.11.5

  Trialkylmanganese-mediated alkylation of enol phosphates is performed in the presence of a catalytic amount of Pd(PPh3)4. The cross coupling reaction catalyzed by Li2MnCl4 between enol triflates and Grignard reagents is also described.

  在催化量 Pd(PPh3)4 的存在下，进行了三烷基锰介导的烯醇膦酸盐烷基化反应，还描述了三烯醇膦酸盐与格氏试剂之间在 Li2MnCl4 催化下发生的交叉偶联反应。
• Lewis acid catalyzed allylstannylation of unactivated alkynes
  作者：Yasuhisa Matsukawa、Naoki Asao、Haruo Kitahara、Yoshinori Yamamoto

  DOI：10.1016/s0040-4020(98)01183-1

  日期：1999.3

  The addition of allyltributylstannane 2 to unactivated aromatic alkynes 1 in the presence of catalytic amounts of ZrCl4 or EtAlCl2 produced the stannylated 1,4-dienes 3 with very high regio- and stereoselectivities in good to high yields. The exclusive trans manner of addition was confirmed by 1H NMR analysis of crude reaction mixtures. On the other hand, the stereochemistries of addition products

  加入allyltributylstannane的2至未活化的芳族炔1在催化量的ZrCl的存在4或EtAlCl 2产生的stannylated 1,4-二烯3具有非常高的区域选择性和立体选择性的良好产量高。通过粗反应混合物的1 H NMR分析证实了排他性反式的添加方式。另一方面，由使用脂族乙炔的反应产生的加成产物的立体化学取决于反应条件和路易斯酸的类型。提出了ZrCl 4和EtAlCl 2催化炔烃烯丙基化的机理。
• Allylation of Unactivated and/or Functionalized Alkynes with Allylindiums
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo9701041

  日期：1997.4.1
• Allyl- and Benzylindium Reagents. Carboindation of Carbon−Carbon and Carbon−Nitrogen Triple Bonds
  作者：Naoya Fujiwara、Yoshinori Yamamoto

  DOI：10.1021/jo990160x

  日期：1999.5.1

  The reaction of unactivated simple terminal alkynes 1 with allylindiums in THF proceeded smoothly to give the corresponding allylation products 2 in good to high yields. This result is in marked contrast to that of the reaction carried out in DMF, where the allylation of unactivated alkynes was very sluggish. The allylic group of the reagent was attached to the internal carbon of the triple. bond, and indium was attached to the less substituted terminal carbon, except for the case of TMS substituted acetylenes 1j and 1k in which the allyl group went to the less substituted carbon of the triple band. The reaction of unactivated simple terminal and certain internal acetylenes with benzylindium in THF proceeded smoothly to afford the corresponding benzylation products 18 in good to high yields. The benzyl group was attached to the less substituted unhindered carbon of the triple bond, and indium was attached to the more sterically congested carbon. The reaction of activated nitriles 3 with allylindiums in THF at 70 degrees C gave the corresponding allylation-enamination products 4 in high to excellent yields. This reaction provides a useful method for the synthesis of highly functionalized enamines, which are not easily available via conventional methods. The mechanisms on the above three indation reactions are discussed.