(Z)-6-bromo-3,4,7,8,9,10-hexahydrobenzo[b][1,5]dioxacyclotetradecin-12(2H)-one | 1426168-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-6-bromo-3,4,7,8,9,10-hexahydrobenzo[b][1,5]dioxacyclotetradecin-12(2H)-one
• 英文别名: (6Z)-7-bromo-2,12-dioxabicyclo[12.4.0]octadeca-1(18),6,14,16-tetraen-13-one
• CAS: 1426168-83-3
• 化学式: C₁₆H₁₉BrO₃
• 分子量: 339.229
• InChiKey: MTVUZYURGMYVDV-QPEQYQDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-6-bromo-3,4,7,8,9,10-hexahydrobenzo[b][1,5]dioxacyclotetradecin-12(2H)-one 、 3-乙酰基苯硼酸 在 二(三叔丁基膦)钯 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以90%的产率得到(Z)-6-(3-acetylphenyl)-3,4,7,8,9,10-hexahydrobenzo[b][1,5]dioxacyclotetradecin-12(2H)-one
  参考文献：
  名称：

  Selective Access to Trisubstituted Macrocyclic E- and Z-Alkenes from the Ring-Closing Metathesis of Vinylsiloxanes

  摘要：

  Macrocyclic (E)-alkenylsiloxanes, obtained from E-selective ring-closing metathesis reactions, can be converted to the corresponding (Z)-alkenyl bromides and (E)-alkenyl iodides allowing access to both E- and Z-trisubstituted macrocyclic alkenes. The reaction conditions and substrate scope of these stereoselective transformations are explored.

  DOI：

  10.1021/ol400134d
• 作为产物：
  描述：

  5-(diethoxy(methyl)silyl)hex-5-en-1-yl 2-(pent-4-en-1-yloxy)benzoate 在 dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II) 、 溴 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.75h， 生成 (Z)-6-bromo-3,4,7,8,9,10-hexahydrobenzo[b][1,5]dioxacyclotetradecin-12(2H)-one
  参考文献：
  名称：

  Selective Access to Trisubstituted Macrocyclic E- and Z-Alkenes from the Ring-Closing Metathesis of Vinylsiloxanes

  摘要：

  Macrocyclic (E)-alkenylsiloxanes, obtained from E-selective ring-closing metathesis reactions, can be converted to the corresponding (Z)-alkenyl bromides and (E)-alkenyl iodides allowing access to both E- and Z-trisubstituted macrocyclic alkenes. The reaction conditions and substrate scope of these stereoselective transformations are explored.

  DOI：

  10.1021/ol400134d

文献信息

• Selective Access to Trisubstituted Macrocyclic <i>E</i>- and <i>Z</i>-Alkenes from the Ring-Closing Metathesis of Vinylsiloxanes
  作者：Yikai Wang、Miguel Jimenez、Patrick Sheehan、Cheng Zhong、Alvin W. Hung、Chun Pong Tam、Damian W. Young

  DOI：10.1021/ol400134d

  日期：2013.3.15

  Macrocyclic (E)-alkenylsiloxanes, obtained from E-selective ring-closing metathesis reactions, can be converted to the corresponding (Z)-alkenyl bromides and (E)-alkenyl iodides allowing access to both E- and Z-trisubstituted macrocyclic alkenes. The reaction conditions and substrate scope of these stereoselective transformations are explored.