triallylaluminum | 18854-66-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 烯丙基金属
• 英文名称: triallylaluminum
• 英文别名: triallylalane
• CAS: 18854-66-5
• 化学式: C₉H₁₅Al
• 分子量: 150.2
• InChiKey: NYCCIXSSBIMHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  苯甲酸苯酯 、 triallylaluminum 以 乙醚 为溶剂， 反应 0.5h， 以98%的产率得到diallyl carbinol
  参考文献：
  名称：

  An efficient of Grignard-type procedure for the preparation of gem-diallylated compound

  摘要：

  An efficient and a new procedure for the conversion of various carboxylic acid derivatives into the corresponding gemdiallylated compound under mild reaction condition has been developed. The triallyaluminum mediated Grignard-type addition of carboxylic acid derivative was utilized as a key operation to affect the transformation. The procedure is operationally simple, giving good to excellent product yields for a broad range of substrates. The chemoselectivity and regioselectivity of triallylaluminum were also demonstrated. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.008

文献信息

• Total Synthesis of Gambierol: The Generation of the A–C and F–H Subunits by Using a C-Glycoside Centered Strategy
  作者：Utpal Majumder、Jason M. Cox、Henry W. B. Johnson、Jon D. Rainier

  DOI：10.1002/chem.200500993

  日期：2006.2.8

  Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3-diaxial orientation to one another. Herein we describe the generation of gambierol's A-C and F-H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether-olefin RCM strategy to fused polycyclic

  甘比罗尔（Gambierol）是海洋梯形毒素家族的代表，由八个醚环，18个立体中心和两个具有挑战性的吡喃基环组成，这些环具有彼此成1,3双轴取向的甲基。在本文中，我们描述了甘氨醇的AC和FH环系统的产生，并展示了糖基酸酐，烯醇醚-烯烃RCM策略对稠合多环醚的多功能性。这项工作不仅使我们能够生成足够数量的甘比罗尔前体，而且使我们能够更好地理解对于这些努力至关重要的化学转化。基础工作包括对C-糖苷和C-酮苷的研究，克莱森重排以及烯醇醚-烯烃RCM反应。
• Modular and Highly Stereoselective Approach to All-Carbon Tetrasubstituted Alkenes
  作者：Vladislav Kotek、Hana Dvořáková、Tomáš Tobrman

  DOI：10.1021/ol503624v

  日期：2015.2.6

  A modular and completely stereoselective approach for the construction of all-carbon tetrasubstituted alkenes is described. It is based on the three-fold, sequential metal-catalyzed, cross-coupling functionalization of simple enolphosphate dibromide templates with carbon nucleophiles, affording tetrasubstituted alkenes as single isomers.

  描述了用于构建全碳四取代烯烃的模块化且完全立体选择的方法。它基于简单的烯醇磷酸盐二溴化物模板与碳亲核试剂的三重，顺序金属催化，交叉偶联官能化，提供四取代的烯烃作为单一异构体。
• Novel and Efficient Method for the Allylation of Carbonyl Compounds and Imines Using Triallylaluminum
  作者：Kao-Hsien Shen、Ching-Fa Yao

  DOI：10.1021/jo052385f

  日期：2006.5.1

  triallylaluminum as a reagent for the allylation of carbonyl compounds and imines. The allylation of ketimines without additional metal catalyst is known so far only in the case of the Grignard reagent. Triallylaluminum is a useful alternative to provide the homoallylic amines in excellent yield upon addition to aldimines and ketimines. The significant reactivity of this reagent was confirmed by its

  这是首次使用三烯丙基铝作为羰基化合物和亚胺的烯丙基化试剂的报道。迄今仅在格氏试剂的情况下才知道没有附加金属催化剂的酮亚胺的烯丙基化。三烯丙基铝是添加到醛亚胺和酮亚胺中后以优异产率提供均烯丙基胺的有用替代品。该试剂与空间刚性的酮（如金刚烷酮）反应，以98％的收率提供1-金刚烷基-3-丁烯-1-醇，证实了该试剂的显着反应性。通过使用不同的酮酸酯证明了三烯丙基铝的化学选择性。值得注意的是，三烯丙基铝是由烯丙基溴和铝金属而不是格氏试剂制得的，并且该过程操作简单，从而导致了良好的产品收率。
• Preparation of 2-alkyl-1,4-naphthoquinones
  作者：William G. Peet、Wilson Tam

  DOI：10.1039/c39830000853

  日期：——

  The reaction of 2,3-dichloro-1,4-naphthoquinone with organo aluminium, zinc, zirconium, or tin reagents yields 2-alkyl-3-chloro-1,4-naphthoquinones; with Zr or Sn reagents, palladium or nickel catalyst is needed.

  2,3-二氯-1,4-萘醌与有机铝，锌，锆或锡试剂的反应生成2-烷基-3-氯-1,4-萘醌；使用Zr或Sn试剂时，需要钯或镍催化剂。
• On the scope of diastereoselective allylation of various chiral glyoxylic oxime ethers with allyltributylstannane in the presence of a Lewis acid and triallylaluminum
  作者：Neelesh A. Kulkarni、Ching-Fa Yao、Kwunmin Chen

  DOI：10.1016/j.tet.2007.05.091

  日期：2007.8

  The nucleophilic allylation of various chiral auxiliaries derived glyoxylic oxime ethers was studied. The use of allyltributylstannane in the presence of a Lewis acid and triallylaluminum provided the corresponding homoallylic amines in high chemical yields (up to 89%) and excellent stereoselectivities (up to >99%). The stereochemical bias of the allylation is proposed.

  研究了各种手性助剂衍生的乙醛酸肟醚的亲核烯丙基化。在路易斯酸和三烯丙基铝存在下使用烯丙基三丁基锡烷以高化学产率（高达89％）和出色的立体选择性（高达> 99％）提供了相应的均烯丙基胺。提出了烯丙基化的立体化学偏倚。