4,4-dimethyl-1-[(dichlorobutyl)stannyl]-3-pentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-dimethyl-1-[(dichlorobutyl)stannyl]-3-pentanone
• 化学式: C₁₁H₂₂Cl₂OSn
• 分子量: 359.911
• InChiKey: VRDGSTLMPPDRBO-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：
  7
• 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：

  4,4-dimethyl-1-[(dichlorobutyl)stannyl]-3-pentanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 2,2-dimethyl-7-hydroxy-3-tridecanone
  参考文献：
  名称：

  阴离子策略，用于三组分和四组分偶联反应，可基于二硫代酮α，β-二阴离子的乙烯基转化而生成酮骨架。

  摘要：

  [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。

  DOI：

  10.1021/ol050813y

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。
• Conjugate addition of zincates derived from ketone α,β-dianions to enones. An access to unsymmetrical 1,6-diketones
  作者：Ilhyong Ryu、Masanobu Ikebe、Noboru Sonoda、Shin-ya Yamato、Go-hei Yamamura、Mitsuo Komatsu

  DOI：10.1016/s0040-4039(00)00925-4

  日期：2000.7

  The conjugate addition of organozincates derived from ketone α,β-dianions to enones was examined. Good yields of unsymmetrical 1,6-diketones were obtained by this reaction. A mixed zincate consisting of the dianion and methyllithium in a 2:1 ratio gave results which were comparable to those of an unmixed dianion zincate.

  共轭加成由酮衍生α的organozincates，β -二价阴离子以烯酮进行了研究。通过该反应获得了不对称的1，6-二酮的良好产率。由二价阴离子和甲基锂以2：1的比例组成的混合锌酸盐的结果与未混合的二价阴离子锌酸盐的结果相当。
• Chelation-Aided Generation of Ketone α,β-Dianions and Their Use as Copper Ate Complexes. Unprecedented Enolate Intervention in the Conjugate Addition to Enones
  作者：Ilhyong Ryu、Hiroyuki Nakahira、Masanobu Ikebe、Noboru Sonoda、Shin-ya Yamato、Mitsuo Komatsu

  DOI：10.1021/ja993577t

  日期：2000.2.1
• 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.