but-2-enylzinc bromide | 111195-58-5

• 分子结构分类: 有机化合物 - 有机金属化合物
• 英文名称: but-2-enylzinc bromide
• 英文别名: (crotyl)zinc bromide；crotylzinc bromide；bromure de crotylzinc
• CAS: 111195-58-5
• 化学式: C₄H₇BrZn
• 分子量: 200.394
• InChiKey: CEHQVABBLRDOPX-CZEFNJPISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  6.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-叔丁基环己酮 、 but-2-enylzinc bromide 生成 4-t-Butyl-1-(1-methylallyl)cyclohexanol
  参考文献：
  名称：

  MLADENOVA M.; BLAGOE B.; GAUDEMAR M.; GAUDEMAR-BARDONE F.; LALLEMAND J. Y+, TETRAHEDRON, 1981, 37, NO 11, 2157-2163

  摘要：

  DOI：
• 作为产物：
  描述：

  丁-2-烯氯化镁 、 zinc dibromide 以 四氢呋喃 为溶剂， 生成 but-2-enylzinc bromide
  参考文献：
  名称：

  关于BF 3中非对映选择性的逆转，促进了巴豆基有机金属化合物向醛的添加

  摘要：

  在巴豆基有机金属试剂C 4 H 7 MLn（1）（M = Cu，Cd，Hg，Tl，Ti，Zr和V）中添加苯甲醛和BF 3 ·OEt 2的混合物主要产生赤型均烯丙基醇与α-加合物一样，在没有BF 3 ·OEt 2的情况下，优先形成苏式异构体。

  DOI：

  10.1016/0022-328x(85)80039-5

文献信息

• Formation of<i>O</i>-Allyl Oximes by Reaction of Allylzinc Reagents with α-Chloronitroso Compounds
  作者：Norbert Sewald、Sorin V. Filip

  DOI：10.1055/s-2005-918429

  日期：——

  The reaction of α-chloronitrosocyclohexane with allyl­zinc reagents in THF selectively provides O-allylcyclohexanone oximes in very good yields in an ene type reaction followed by zinc halide elimination. N-Allyl hydroxylamines are formed as minor products via N-allyl nitrones when a nonpolar solvent, e.g. toluene, is employed. In both cases complete allylic transposition with respect to the allylic organozinc reagent is observed. Compared to non-metalated allyl compounds, which give N-allyl nitrones upon reaction with α-chloronitroso compounds, the use of zinc as hydrogen equivalent in an ene type reaction displays a drastic change of reactivity.

  α-氯亚硝基环己烷与烯丙基锌试剂在THF中反应，选择性地以很高的产率提供O-烯丙基环己酮肟，这是一种ene型反应，随后发生锌卤化物消除。当使用非极性溶剂（例如甲苯）时，会形成N-烯丙基羟肟作为少量产物，产物的形成途径是通过N-烯丙基亚硝酮。在这两种情况下，完全的烯丙基转位相对于烯丙基有机锌试剂被观察到。与非金属化的烯丙基化合物相比，后者在与α-氯亚硝基化合物反应时形成N-烯丙基亚硝酮，使用锌作为氢的等价物在ene型反应中显示出反应性发生了剧烈变化。
• Synthesis of 3-Ethoxycarbonyl-3-buten-4-olides and 3-Ethoxycarbonyl-4-butanolides
  作者：Françoise Gaudemar-Bardone、Margarita Mladenova、RENÉ Couffignal

  DOI：10.1055/s-1985-31423

  日期：——

  This paper describes a synthesis of 3-acyl-2-alkyl-3-ethoxycarbonylpropanoic acids from ethyl 2-oxoalkanoates and 2-bromoalkanoic acids. These acids are cyclised via intramolecular dehydration to give 2,4-dialkyl-3-ethoxycarbonyl-3-buten-4-olides or are condensed with allylzinc reagents to give the 4-alkenyl-2,4-dialkyl-3-ethoxycarbonyl-4-butanolides.

  本文描述了从乙基2-氧羧酸酯和2-溴烷酸合成3-酰基-2-烷基-3-乙氧基碳酰基丙酸。这些酸通过分子内脱水环化，生成2,4-二烷基-3-乙氧基碳酰基-3-丁烯-4-内酯，或者与烯丙基锌试剂缩合，生成4-烯基-2,4-二烷基-3-乙氧基碳酰基-4-内酯。
• Diastereoselective Addition of Allylzinc Bromide to Imines Derived from (<i>R</i>)-Phenylglycine Amide
  作者：Marcel van der Sluis、Jan Dalmolen、Ben de Lange、Bernard Kaptein、Richard M. Kellogg、Quirinus B. Broxterman

  DOI：10.1021/ol016840f

  日期：2001.11.1

  The highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. Homoallylamines with high enantiomeric purity are obtained from the adducts in three steps on removal of the chiral auxiliary by means of a nonreductive protocol. Removal of the auxiliary by hydrogenation leads to the saturated amines, also in high enantiomeric purity. [reaction: see

  据报道，将烯丙基溴锌高度非对映选择性地加到衍生自（R）-苯基甘氨酸酰胺的亚胺上。具有高对映体纯度的高烯丙胺是在通过非还原方案去除手性助剂的三个步骤中从加合物获得的。通过氢化除去助剂得到饱和胺，也具有高对映体纯度。[反应：看文字]
• Propargyl and allyl Grignard and zinc reagents. Regioselective alkylation and its application to the synthesis of PGE3 and F3.alpha. methyl ester
  作者：Akira Yanagisawa、Shigeki Habaue、Hisashi Yamamoto

  DOI：10.1021/jo00283a004

  日期：1989.10
• Multicomponent Radical Processes:  Synthesis of Substituted Piperidinones
  作者：Edouard Godineau、Yannick Landais

  DOI：10.1021/ja075755l

  日期：2007.10.1

  Three and four-component radical and radical-organometallic processes have been developed that provide a simple access to 2,3disubstituted piperidinones. Reasonable yield and high stereoselectivities were achieved in a number of cases with three C-C bonds and one C-N bond and up to three stereogenic centers generated in one pot from readily available reagents.