(1R,5R,8S)-8-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-2-oxabicyclo<3.2.1>octan-3-one | 163622-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,5R,8S)-8-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-2-oxabicyclo<3.2.1>octan-3-one
• 英文别名: (1R,5R,8S)-8-[(Z)-5-(oxan-2-yloxy)pent-2-enyl]-2-oxabicyclo[3.2.1]octan-3-one
• CAS: 163622-32-0
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: RULXXEYEVXZGQI-GDDKTCBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5R,8S)-8-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-2-oxabicyclo<3.2.1>octan-3-one 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 2-((1R,2S,3R)-3-hydroxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)cyclopentyl)ethanoic acid
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x
• 作为产物：
  描述：

  (1R,5R,8S)-8-(1',3'-dithianyl-2')methyl-2-oxabicyclo[3,2,1]octan-3-one 在 phosphate buffer 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 碘甲烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.0h， 生成 (1R,5R,8S)-8-(5-2'-tetrahydropyranyloxy-cis-2-pentenyl)-2-oxabicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x

文献信息

• Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer
  作者：Munenori Inoue、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00157-x

  日期：1999.4

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.