(Z)-5-bromo-4-methylpenta-1,3-diene | 1447829-96-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (Z)-5-bromo-4-methylpenta-1,3-diene
• 英文别名: (3Z)-5-bromo-4-methylpenta-1,3-diene
• CAS: 1447829-96-0
• 化学式: C₆H₉Br
• 分子量: 161.041
• InChiKey: OXVZQLMBFUTCBX-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  7
• 可旋转键数：
  2
• 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：

  (Z)-5-bromo-4-methylpenta-1,3-diene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium periodate 、 锂硼氢 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.25h， 生成 (6R,7S,8S,9S)-2,2,6,8,12,12,13,13-octamethyl-9-((Z)-2-methyl-4-oxobut-2-en-1-yl)-3,3-diphenyl-4,11-dioxa-3,12-disilatetradecan-7-yl (R)-2-methoxybut-3-enoate
  参考文献：
  名称：

  Construction of the A ring of halichomycin via a RCM strategy

  摘要：

  Attempts to the synthesis of the A ring of halichomycin via ring-closing metathesis (RCM) reaction were investigated. When triene 5 was used as the precursor of cyclization, only unexpected byproduct aldehyde 17 was obtained. When diene 6 was used as the precursor of cyclization, the desired product 20 was obtained in reasonable yield. This work demonstrated that both modification of the substrate and the RCM reaction conditions are important for obtaining the desired 11-membered macrocycle in reasonable yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.027
• 作为产物：
  描述：

  (Z)-2-methyl-2,4-pentadien-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (Z)-5-bromo-4-methylpenta-1,3-diene
  参考文献：
  名称：

  Construction of the A ring of halichomycin via a RCM strategy

  摘要：

  Attempts to the synthesis of the A ring of halichomycin via ring-closing metathesis (RCM) reaction were investigated. When triene 5 was used as the precursor of cyclization, only unexpected byproduct aldehyde 17 was obtained. When diene 6 was used as the precursor of cyclization, the desired product 20 was obtained in reasonable yield. This work demonstrated that both modification of the substrate and the RCM reaction conditions are important for obtaining the desired 11-membered macrocycle in reasonable yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.027

文献信息

• An Efficient Synthesis of the Fully Elaborated Isoindolinone Unit of Muironolide A
  作者：Qing Xiao、Kyle Young、Armen Zakarian

  DOI：10.1021/ol401354a

  日期：2013.7.5

  An efficient stereocontrolled construction of the fully substituted isoindolone subunit of muironolide A is described. The approach is centered on the intramolecular Diels-Alder reaction between the enol form of the beta-keto amide and an alpha,beta,gamma,delta-unsaturated ester, followed by the installation of the cyclohexene double bond.