3-[2-(3-bromo-propyl)-phenyl]-acrylic acid | 385806-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[2-(3-bromo-propyl)-phenyl]-acrylic acid
• 英文别名: (E)-3-[2-(3-bromopropyl)phenyl]prop-2-enoic acid
• CAS: 385806-08-6
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: MYAOHONFKJOEIL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[2-(3-bromo-propyl)-phenyl]-acrylic acid 在 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R)-1,2,3,4-tetrahydronaphthalen-1-ylacetic acid
  参考文献：
  名称：

  Highly Diastereoselective Radical Cyclizations on Soluble Ring Opening Metathesis Supports

  摘要：

  [GRAPHICS]This study represents the first examples of stereoselective radical cyclizations on soluble supports. A stereocontrol element consisting of a polymer-imbedded (+)-isosorbide chiral auxiliary was used in each monomer subunit. A survey of various Lewis acids was also examined. The best results gave very high distereoselectivites of > 100:1 in a hepa-1,3-dienenyl radical cyclization using zinc chloride as a Lewis acid.

  DOI：

  10.1021/ol016855d
• 作为产物：
  描述：

  1,2-二氢萘 在 manganese(IV) oxide 、 lithium hydroxide 、 2,3-二巯基丁二酸 、 四溴化碳 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 3-[2-(3-bromo-propyl)-phenyl]-acrylic acid
  参考文献：
  名称：

  Highly Diastereoselective Radical Cyclizations on Soluble Ring Opening Metathesis Supports

  摘要：

  [GRAPHICS]This study represents the first examples of stereoselective radical cyclizations on soluble supports. A stereocontrol element consisting of a polymer-imbedded (+)-isosorbide chiral auxiliary was used in each monomer subunit. A survey of various Lewis acids was also examined. The best results gave very high distereoselectivites of > 100:1 in a hepa-1,3-dienenyl radical cyclization using zinc chloride as a Lewis acid.

  DOI：

  10.1021/ol016855d

文献信息

• Highly Diastereoselective Radical Cyclizations on Soluble Ring Opening Metathesis Supports
  作者：Eric J. Enholm、Jennifer S. Cottone

  DOI：10.1021/ol016855d

  日期：2001.11.1

  [GRAPHICS]This study represents the first examples of stereoselective radical cyclizations on soluble supports. A stereocontrol element consisting of a polymer-imbedded (+)-isosorbide chiral auxiliary was used in each monomer subunit. A survey of various Lewis acids was also examined. The best results gave very high distereoselectivites of > 100:1 in a hepa-1,3-dienenyl radical cyclization using zinc chloride as a Lewis acid.