3-((1R*,2S*,4R*,5R*)-3,6-dioxa-2,4,5-trimethyl-bicyclo[3.1.0]hex-2-yl)-2-methylacrylic acid ethyl ester | 109770-70-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-((1R*,2S*,4R*,5R*)-3,6-dioxa-2,4,5-trimethyl-bicyclo[3.1.0]hex-2-yl)-2-methylacrylic acid ethyl ester
• 英文别名: ethyl (E)-2-methyl-3-[(1R,2R,4S,5S)-2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl]prop-2-enoate
• CAS: 109770-70-9；109770-80-1；115186-63-5
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: JIPKBSADKPBESV-OPKFUAESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((1R*,2S*,4R*,5R*)-3,6-dioxa-2,4,5-trimethyl-bicyclo[3.1.0]hex-2-yl)-2-methylacrylic acid ethyl ester 在 高氯酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 11.0h， 生成 (+/-)-(2S^*,3S^*,4S^*,5R^*)-2-<3-hydroxy-2-methyl-1(E)-propenyl>-2,4,5-trimethyl-2,3,4,5-tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Synthesis of (±)-5-epi-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation

  摘要：

  The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.

  DOI：

  10.1021/ol026343e
• 作为产物：
  描述：

  4,5-二甲基-2-呋喃甲酸 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 2.25h， 生成 3-((1R*,2S*,4R*,5R*)-3,6-dioxa-2,4,5-trimethyl-bicyclo[3.1.0]hex-2-yl)-2-methylacrylic acid ethyl ester
  参考文献：
  名称：

  Verrucosidin的合成研究：（±）verrucosal的合成

  摘要：

  Verrucosal是Verrucosidin的主要降解产物，是通过短而直接的途径由4,5-二甲基-2-糠酸以消旋形式合成的。

  DOI：

  10.1016/s0040-4039(00)84999-0

文献信息

• Synthesis of (±)-5-<i>e</i><i>pi</i>-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation
  作者：Zhi-Hui Peng、K. A. Woerpel

  DOI：10.1021/ol026343e

  日期：2002.8.1

  The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has been accomplished with this annulation reaction as the key step. Using the pantolactone-derived alpha-keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.
• Synthetic studies toward verrucosidin: Synthesis of (±)verrucosal
  作者：Larry L Klein

  DOI：10.1016/s0040-4039(00)84999-0

  日期：——

  Verrucosal, , a major degradation product of verrucosidin was synthesized in racemic form by a short and direct route from 4,5-dimethyl-2-furoic acid.

  Verrucosal是Verrucosidin的主要降解产物，是通过短而直接的途径由4,5-二甲基-2-糠酸以消旋形式合成的。