(1R,2S,5R,6R)-2-azido-5,6-O-(isopropylidenedioxy)-4-(thiophen-3'-yl)cyclohex-3-ene-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,5R,6R)-2-azido-5,6-O-(isopropylidenedioxy)-4-(thiophen-3'-yl)cyclohex-3-ene-1-ol
• 英文别名: (3aS,4R,5S,7aR)-5-azido-2,2-dimethyl-7-thiophen-3-yl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• 化学式: C₁₃H₁₅N₃O₃S
• 分子量: 293.346
• InChiKey: BAHXLTCKUJXZFH-QCNOEVLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [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 、 3-噻吩三氟硼酸钾 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 5.5h， 以50%的产率得到(1R,2S,5R,6R)-2-azido-5,6-O-(isopropylidenedioxy)-4-(thiophen-3'-yl)cyclohex-3-ene-1-ol
  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.