(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene | 596834-79-6

• 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: (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene
• 英文别名: (3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-5-phenylmethoxy-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 596834-79-6
• 化学式: C₁₆H₁₉BrO₄
• 分子量: 355.228
• InChiKey: YWQHUEDEPNKZCE-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene 在 草酰氯 、 [CH₃OCH₂CH₂]NSF₃ 、 camphor-10-sulfonic acid 、 二甲基亚砜 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (2S,3S,4aS,8R,8aR)-8-Benzyloxy-6-bromo-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5
• 作为产物：
  描述：

  溴甲苯 、 [3aS-(3aα,4α,5α,7aα)]-7-溴-3a,4,5,7a-四氢-2,2-二甲基-1,3-苯并二茂-4,5-二醇 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 以63%的产率得到(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene
  参考文献：
  名称：

  Difluorinated analogues of shikimic acid

  摘要：

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00697-5