(Z)-1-Bromo-1-trimethylsilylpenta-1,4-diene | 85052-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-Bromo-1-trimethylsilylpenta-1,4-diene
• 英文别名: (Z)-1-bromo-1-trimethylsilyl-1,4-pentadiene；1-bromo-1-trimethylsilyl-1(Z),4-pentadiene；[(1Z)-1-bromopenta-1,4-dienyl]-trimethylsilane
• CAS: 85052-00-2
• 化学式: C₈H₁₅BrSi
• 分子量: 219.197
• InChiKey: USRJTXZSCJDPDE-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (Z)-1-Bromo-1-trimethylsilylpenta-1,4-diene 在 copper(l) iodide 、 magnesium 、 1,2-二溴乙烷 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 trimethyl-[(1R,2R)-2-(3-prop-2-enyl-2-trimethylsilyloxiran-2-yl)cyclohexyl]oxysilane
  参考文献：
  名称：

  Yamaguchi, R.; Kawasaki, H.; Kawanisi, M., Synthetic Communications, 1982, vol. 12, # 13, p. 1027 - 1038

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴丙烯 、 三甲基乙炔基硅 在 bis(acetonitrile)palladium(II) bromide 作用下， 以62%的产率得到(Z)-1-Bromo-1-trimethylsilylpenta-1,4-diene
  参考文献：
  名称：

  两步法作为由Ni（CO）4介导的烯丙基卤和乙炔衍生物环羰基化的改进替代方法

  摘要：

  在Pd（II）配合物（如双乙腈钯（II）溴化物）催化的炔属衍生物中添加烯丙基卤化物，然后在含精确量CH 3的CH 3 CN中用Ni（CO）4环化所得的加合物。OH和Et 3 N比由Ni（CO）4介导的这些底物进行直接环羰基化来制备环戊烯，特别是对于单取代的乙炔或弱极化的二取代的乙炔而言，是一种更好的方法。

  DOI：

  10.1016/s0040-4039(00)82199-1

文献信息

• Ni-promoted Cyclopentenone Formation by Intramolecular Cyclocarbonylation of 1-Bromo-1,4-dienes
  作者：Amadeu Llebaria、Francisco Camps、Josep Ma Moretó

  DOI：10.1016/s0040-4020(01)85818-x

  日期：1993.2

  the formation of 1-bromo-1,4-dienes which were further converted to cyclopentenones through a Ni(CO)4 promoted carbonylation-cyclization process. Four CC bonds are formed by this two step sequence, leading to 2,3-substituted 5-methoxycarbonylmethylcyclopentenones 1. Application of this procedure to 2-butyne affords cyclopentenone 1c, an immediate precursor of the antibiotic methylenomicyn B.

  立体选择性合成除了烯丙基溴通过在1-溴-1,4-二烯，其进一步通过的Ni（CO）转化为环戊烯酮的形成钯（II），溴化结果催化乙炔4促进的羰基化的环化过程。通过这两个步骤序列形成四个CC键，从而生成2，3-取代的5-甲氧羰基甲基环戊烯酮1。将该方法应用于2-丁炔，可得到环戊烯酮1c，即抗生素甲基enomicyn B的直接前体。
• A New Synthetic Approach to Phenol Derivatives:  Use of Ring-Closing Olefin Metathesis
  作者：Kazuhiro Yoshida、Tsuneo Imamoto

  DOI：10.1021/ja050853x

  日期：2005.8.1

  Phenol derivatives, which are one of the most important classes of aromatic compounds in organic chemistry, were synthesized by ruthenium-catalyzed ring-closing olefin metathesis (RCM) of 1,4,7-trien-3-ones with versatile substitution patterns. The RCM reaction for producing phenol derivatives was also successful with 1,5,7-trien-3-one as another precursor. Most of the phenols prepared here could not

  苯酚衍生物是有机化学中最重要的一类芳族化合物，通过钌催化的 1,4,7-trien-3-ones 的闭环烯烃复分解 (RCM) 合成，具有多种取代模式。以 1,5,7-trien-3-one 作为另一种前体，用于生产苯酚衍生物的 RCM 反应也取得了成功。此处制备的大部分酚类无法通过常规方法轻易获得。
• Carboindation of Carbon−Carbon Triple Bonds:  Regioselective Indium-Mediated Allylation of Functionalized Alkynes and Transformation into Halogen-Substituted 1,4-Dienes
  作者：Ernst Klaps、Walther Schmid

  DOI：10.1021/jo9908593

  日期：1999.10.1

  By examining the allylindation of a series of substituted alkynes, the relationships between allylindation reactivity and alkyne structure were systematically investigated. While terminal alkynes with protected hydroxyl groups gave the corresponding allylated branched 1,4-dienes (Markovnikov products) within 5-6 h, the unprotected alkynols reacted markedly faster, requiring only 2-4 h of ultrasonication in THF to produce the 1,4-dienols in good yields. In the latter reactions, the regioisomeric outcome was found to depend on the distance between the hydroxyl group and the alkyne moiety: propargylic substrates gave linear 1,4-dienes (anti-Markovnikov products), suggesting the involvement of bicyclic "chelation-controlled" transition state, while 4-pentynol and higher homologues exclusively afforded the branched 1,4-dienes. Moreover, the proposed vinylic alpha,alpha-bis-indium intermediates from both protected and unprotected substrates were successfully quenched with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) to form tri- and tetrasubstituted dienes in good yields. Taken as a whole, these results illustrate the remarkable stability of the allylindium and vinylindium intermediates despite the presence of protic functionalities in the reaction mixture.
• YAMAGUCHI, R.;KAWASAKI, H.;KAWANISI, M., SYNTH. COMMUN., 1982, 12, N 13, 1027-1037
  作者：YAMAGUCHI, R.、KAWASAKI, H.、KAWANISI, M.

  DOI：——

  日期：——
• CAMPS, F.;COLL, J.;LLEBARIA, A.;MORETO, J. M., TETRAHEDRON LETT., 29,(1988) N 45, C. 5811-5814
  作者：CAMPS, F.、COLL, J.、LLEBARIA, A.、MORETO, J. M.

  DOI：——

  日期：——