3-((2R,4aR,8S,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-but-3-en-2-one | 1054656-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 3-((2R,4aR,8S,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-but-3-en-2-one
• 英文别名: 3-[[(2R,4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]but-3-en-2-one
• CAS: 1054656-39-1
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: CNOOEEPCWPWEQL-VVLHAWIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-((2R,4aR,8S,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-but-3-en-2-one 以 xylene 为溶剂， 以99%的产率得到1-((2R,4aR,6R,8aS)-2-Phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butane-2,3-dione
  参考文献：
  名称：

  Synthesis of α-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement

  摘要：

  A variety of alpha-C-glycosides may be accessed in an entirely stercoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding beta-series, careful control of conditions for Claisen rearrangement is required in order to avoid loss of integrity of anomeric stereochemistry; thermal rearrangements are best carried out in xylene in a sealed tube. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00710-x
• 作为产物：
  描述：

  1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 3-((2R,4aR,8S,8aS)-2-Phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-but-3-en-2-one
  参考文献：
  名称：

  Synthesis of α-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement

  摘要：

  A variety of alpha-C-glycosides may be accessed in an entirely stercoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding beta-series, careful control of conditions for Claisen rearrangement is required in order to avoid loss of integrity of anomeric stereochemistry; thermal rearrangements are best carried out in xylene in a sealed tube. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00710-x

文献信息

• Synthesis of α-C-glycosides via tandem Tebbe methylenation and Claisen rearrangement
  作者：H.Yasmin Godage、Antony J. Fairbanks

  DOI：10.1016/s0040-4039(03)00710-x

  日期：2003.4

  A variety of alpha-C-glycosides may be accessed in an entirely stercoselective fashion from 3-OH glycal esters, by way of the tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. In contrast with previous studies in the corresponding beta-series, careful control of conditions for Claisen rearrangement is required in order to avoid loss of integrity of anomeric stereochemistry; thermal rearrangements are best carried out in xylene in a sealed tube. (C) 2003 Elsevier Science Ltd. All rights reserved.