β-dichlorobutylstannyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-dichlorobutylstannyl ketone
• 化学式: C₁₁H₂₂Cl₂OSn
• 分子量: 359.911
• InChiKey: WABJFIYHOAATGF-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-环己烯-1-酮 、 β-dichlorobutylstannyl ketone 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到1-[5-hydroxybicyclo[3.2.1]oct-6-yl]-2-methyl-1-butanone
  参考文献：
  名称：

  螯合辅助生成酮 α，β-二价阴离子及其作为铜盐配合物的用途。对烯酮共轭添加的前所未有的烯醇化干预

  摘要：

  DOI：

  10.1021/ja993577t

文献信息

• Reactions of ketone dilithio α,β-dianions with imines and hydrazones: an anionic access to γ-amino ketones
  作者：Ilhyong Ryu、Go-hei Yamamura、Sohei Omura、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1016/j.tetlet.2006.02.026

  日期：2006.4

  The reactions of ketone dilithio α,β-dianions with imines and hydrazones were investigated. The nucleophilic addition reaction to C–N double bonds took place selectively at the β-position of dianions to form lithium Z-enolates containing a lithium amide portion, which is then transformed into γ-amino ketones and related compounds by the subsequent reaction with electrophiles.

  研究了酮类二硫代α，β-二价阴离子与亚胺和的反应。C–N双键的亲核加成反应选择性地在二价阴离子的β位置发生，以形成含有锂酰胺部分的Z-烯醇锂，然后通过与亲电试剂的后续反应将其转化为γ-氨基酮和相关化合物。
• Chemistry of ketone α,β-dianions. Acylation reactions of dianion cuprates by acid chlorides
  作者：Ilhyong Ryu、Masanobu Ikebe、Noboru Sonoda、Shin-ya Yamato、Go-hei Yamamura、Mitsuo Komatsu

  DOI：10.1016/s0040-4039(01)02346-2

  日期：2002.2

  The cross-coupling reaction of dianion cuprates, generated from ketone α,β-dianions and copper salts, with acid chlorides, was studied. The reaction gave good to moderate yields of unsymmetrical 1,4-diketones. The consecutive treatment of a dianion cuprate with cyclohexanecarbonyl chloride and methyl iodide or two different acid chlorides gave 2-methyl-substituted 1,4-diketone or triketone, respectively

  研究了由酮α，β-二价阴离子和铜盐生成的二价铜酸盐与酰氯的交叉偶联反应。该反应给出了不对称的1，4-二酮的良好至中等产率。用环己烷羰基氯和碘甲烷或两种不同的酰氯连续处理二价铜酸盐，分别得到2-甲基取代的1，4-二酮或三酮。
• An Anionic Strategy for Three- and Four-Component Coupling Reactions Leading to Ketone Frameworks Based on Vinylogous Conversion of Dilithio Ketone α,β-Dianions
  作者：Shin-ya Yamato、Go-hei Yamamura、Mitsuo Komatsu、Masashi Arai、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1021/ol050813y

  日期：2005.6.1

  [reaction: see text] Ketone alpha,delta-dianions are generated by vinylogous extension of ketone alpha,beta-dianions with alkenes such as vinylarenes, vinylsilanes, and vinyl sulfides, which then undergo reactions at the delta and alpha positions with different electrophiles, creating ketone frameworks. This work represents a cascade-type anion method that achieved three- and four-carbon component

  [反应：请参阅文字]酮α，δ-二价阴离子是通过将酮α，β-二价阴离子与烯键（如乙烯基芳烃，乙烯基硅烷和乙烯基硫化物）乙烯基延伸而产生的，然后这些烯在δ和α位与不同的亲电试剂发生反应，创建酮框架。这项工作代表了一种级联型阴离子方法，该方法实现了三碳和四碳组分的组装反应，从而产生了酮。
• Generation of ketone dilithio α,β-dianions and their reactions with electrophiles
  作者：Hiroyuki Nakahira、Masanobu Ikebe、Yoshiaki Oku、Noboru Sonoda、Takahide Fukuyama、Ilhyong Ryu

  DOI：10.1016/j.tet.2005.01.047

  日期：2005.3

  Ketone dilithio alpha,beta- and alpha,beta'-dianions can be generated by a tin-lithium exchange reaction of the lithium enolate of beta-tributyltin substituted ketones. A chelation-aided approach, which employs beta-dichlorobutyltin substituted ketones and n-BuLi, is also useful for the generation of ketone alpha,beta-dianions having the Z-geometry at the alkene. The generated dianions can be transformed into substituted ketones by reaction with various carbon electrophiles. (c) 2005 Elsevier Ltd. All rights reserved.