(1R,2S,5R)-1,5-dimethyl-2-[(1R)-naphth-2-yl-ethoxy]-8-oxabicyclo[3.2.1]oct-6-en-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S,5R)-1,5-dimethyl-2-[(1R)-naphth-2-yl-ethoxy]-8-oxabicyclo[3.2.1]oct-6-en-3-one
• 英文别名: (1R,2S,5R)-1,5-dimethyl-2-[(1R)-1-naphthalen-2-ylethoxy]-8-oxabicyclo[3.2.1]oct-6-en-3-one
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: ZAMHFKQBYRQBKC-MSPZUWAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二甲基呋喃 、 Triethyl-{1-[methoxy-((R)-1-naphthalen-2-yl-ethoxy)-methyl]-vinyloxy}-silane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以28%的产率得到(1S,2R,5S)-1,5-dimethyl-2-[(1R)-naphth-2-yl-ethoxy]-8-oxabicyclo[3.2.1]oct-6-en-3-one
  参考文献：
  名称：

  High Regio-, Chemo-, and Stereoselectivity via Low-Temperature 4 + 3 Cycloadditions. Convergent Synthesis of Multifunctionalized Vinylmetals (M = Si, Sn) and S-Vinyl Benzenecarbothioates

  摘要：

  [GRAPHICS]A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 degrees C and adjusted to diene nucleophilicity. Conventional electrophilic substitution of 3-silylated and 3-stannylated furan is suppressed in favor of the rapid 4 + 3 cycloaddition mode. In the case of cycloadduct 13A, stereoselectivity (17:1) is perfectly matched to regioselectivity (17:1). High stereoselection as well as unprecedented regioselection and chemoselection is attributed to the low-temperature cycloaddition protocol and the design of chiral auxiliary and tether.

  DOI：

  10.1021/ol991386p

文献信息

• High Regio-, Chemo-, and Stereoselectivity via Low-Temperature 4 + 3 Cycloadditions. Convergent Synthesis of Multifunctionalized Vinylmetals (M = Si, Sn) and <i>S</i>-Vinyl Benzenecarbothioates
  作者：Hartmut Beck、Christian B. W. Stark、H. Martin R. Hoffmann

  DOI：10.1021/ol991386p

  日期：2000.4.1

  [GRAPHICS]A series of enantiomerically pure 8-oxabicyclo[3.2.1]oct-6-en-3-ones functionalized in the unsaturated two-carbon bridge has been prepared by the title reaction. Carbocation reactivity has been fined-tuned at -95 degrees C and adjusted to diene nucleophilicity. Conventional electrophilic substitution of 3-silylated and 3-stannylated furan is suppressed in favor of the rapid 4 + 3 cycloaddition mode. In the case of cycloadduct 13A, stereoselectivity (17:1) is perfectly matched to regioselectivity (17:1). High stereoselection as well as unprecedented regioselection and chemoselection is attributed to the low-temperature cycloaddition protocol and the design of chiral auxiliary and tether.