(1Z,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1Z,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol
• 化学式: C₈H₁₃BrO
• 分子量: 205.095
• InChiKey: RFYOHCOJZFXVNO-SACCCDBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-丁烯-2-醋酸 、 Z-3-bromo-2-methyl-2-propen-1-ol 在 C₄₉H₃₅IrN₂O₈P₂ 、 水 、 sodium carbonate 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 、 对硝基苯甲酸 、 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 149.0h， 生成 (Z,3R,4S)-1-bromo-2,4-dimethyl-3-hydroxyhexa-1,5-diene 、 (1Z,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol
  参考文献：
  名称：

  Synthesis of the Cytotrienin A CoreviaMetal Catalyzed C−C Coupling

  摘要：

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

  DOI：

  10.1021/ol200160p

文献信息

• Synthesis of the Cytotrienin A Core<i>via</i>Metal Catalyzed C−C Coupling
  作者：Michael Rössle、David J. Del Valle、Michael J. Krische

  DOI：10.1021/ol200160p

  日期：2011.3.18

  A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which Is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.