methyl (2S,3S,4aS,8aR)-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-8,8a-dihydro-4aH-1,4-benzodioxine-7-carboxylate | 257876-92-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,4aS,8aR)-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-8,8a-dihydro-4aH-1,4-benzodioxine-7-carboxylate
• CAS: 257876-92-9
• 化学式: C₁₄H₂₀F₂O₆
• 分子量: 322.306
• InChiKey: QSVAWJZYZCXCAV-URBCHYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4aS,8aR)-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-8,8a-dihydro-4aH-1,4-benzodioxine-7-carboxylate 在 三氟乙酸 作用下， 反应 1.5h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of 3-deoxy-3,3-difluoroshikimic acid and its 4-epimer from quinic acid

  摘要：

  3-Deoxy-3,3-difluoroshikimic acid 2 and its 4-epimer 3 as new analogues of shikimic acid have been synthesised from quinic acid in overall yields of 30% and 12%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00447-4
• 作为产物：
  描述：

  (2S,3S,4aR,6S,8R,8aR)-八氢-6,8-二羟基-2,3-二甲氧基-2,3-二甲基-1,4-苯并二氧杂环己-6-羧酸甲酯 在 光气 、 二乙胺基三氟化硫 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 337.0h， 生成 methyl (2S,3S,4aS,8aR)-5,5-difluoro-2,3-dimethoxy-2,3-dimethyl-8,8a-dihydro-4aH-1,4-benzodioxine-7-carboxylate
  参考文献：
  名称：

  Synthesis of 3-deoxy-3,3-difluoroshikimic acid and its 4-epimer from quinic acid

  摘要：

  3-Deoxy-3,3-difluoroshikimic acid 2 and its 4-epimer 3 as new analogues of shikimic acid have been synthesised from quinic acid in overall yields of 30% and 12%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00447-4

文献信息

• Approaches to the synthesis of 3-fluoroshikimic acids
  作者：Lovely Begum、Michael G.B. Drew、Jane L. Humphreys、David J. Lowes、Pamela R. Russi、Helen L. Whitby、Roger C. Whitehead

  DOI：10.1016/j.tetlet.2004.06.092

  日期：2004.8

  Exploitation of the dual dehydrating and fluorodeoxygenating properties of the dialkylaminosulfurtrifluorides has allowed access to the C3-fluorinated analogues of (-)-shikimic acid. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 3-deoxy-3,3-difluoroshikimic acid and its 4-epimer from quinic acid
  作者：Shende Jiang、Gurdial Singh、Deborah J Boam、John R Coggins

  DOI：10.1016/s0957-4166(99)00447-4

  日期：1999.10

  3-Deoxy-3,3-difluoroshikimic acid 2 and its 4-epimer 3 as new analogues of shikimic acid have been synthesised from quinic acid in overall yields of 30% and 12%, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.