(3S,4R,5R,6R)-4-(3-azido-4-hydroxy-5,6-O-(isopropylidenedioxy)cyclohex-1-enyl)benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R,5R,6R)-4-(3-azido-4-hydroxy-5,6-O-(isopropylidenedioxy)cyclohex-1-enyl)benzaldehyde
• 英文别名: 4-[(3aR,6S,7R,7aS)-6-azido-7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-4-yl]benzaldehyde
• 化学式: C₁₆H₁₇N₃O₄
• 分子量: 315.329
• InChiKey: ANKFPXIEAIOFBM-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲酸苯基三氟硼酸钾 、 [3aS-(3aα,4α,5β,7aα)]-5-叠氮-7-溴-3a,4,5,7a-四氢-2,2-二甲基-1,3-苯并二氧杂环戊烷-4-醇 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 以45%的产率得到(3S,4R,5R,6R)-4-(3-azido-4-hydroxy-5,6-O-(isopropylidenedioxy)cyclohex-1-enyl)benzaldehyde
  参考文献：
  名称：

  Synthesis of unnatural cyclitols via a combined enzymatic-palladium catalysis approach

  摘要：

  The Suzuki-Miyaura cross-coupling reaction of a hydroxylated vinyl bromide obtained by a chemoenzymatic approach with a diverse range of potassium organotrifluoroborates has been accomplished catalyzed by Pd(PPh3)(4) in satisfactory yields. A variety of functional groups are tolerated in the nucleophilic partner. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.01.006

文献信息

• Synthesis of unnatural cyclitols via a combined enzymatic-palladium catalysis approach
  作者：Ana Bellomo、David Gonzalez、Hèlio A. Stefani

  DOI：10.1016/j.jorganchem.2008.01.006

  日期：2008.3

  The Suzuki-Miyaura cross-coupling reaction of a hydroxylated vinyl bromide obtained by a chemoenzymatic approach with a diverse range of potassium organotrifluoroborates has been accomplished catalyzed by Pd(PPh3)(4) in satisfactory yields. A variety of functional groups are tolerated in the nucleophilic partner. (C) 2008 Elsevier B.V. All rights reserved.