(2R,3R)-1-(4-methoxyphenoxy)-3-methylpent-4-yne-2,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-1-(4-methoxyphenoxy)-3-methylpent-4-yne-2,3-diol
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: AAFBKGLCAQCKNQ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-iodo-2,5-dimethoxy-3,4,6-trimethylbenzene 、 (2R,3R)-1-(4-methoxyphenoxy)-3-methylpent-4-yne-2,3-diol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二乙胺 作用下， 反应 2.5h， 以53%的产率得到(2R,3R)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-1-(4-methoxyphenoxy)-3-methylpent-4-yne-2,3-diol
  参考文献：
  名称：

  Asymmetric Dihydroxylations of 1-Substituted (E)- and (Z)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished

  摘要：

  Asymmetric dihydroxylations ("ADs") of the pentenynyl chlorides (E)- and (Z)-1 or the pentenyne-based ester (Z)-3 in the presence of (DHQ)(2)-containing ligands delivered diol stereoisomers (2R,3S)-2, (2R,3R)-2, and (3S,4R)-4, respectively. The ADs of pentenynyl ethers (E)-10 and (Z)-12, respectively, have the same stereochemical preference under analogous conditions; these reattributions correct previous reports of the contrary. The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.

  DOI：

  10.1021/ol103063t
• 作为产物：
  描述：

  (E)-1-methoxy-4-(3-methylpent-2-en-4-ynyloxy)benzene 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (2R,3R)-1-(4-methoxyphenoxy)-3-methylpent-4-yne-2,3-diol
  参考文献：
  名称：

  Asymmetric Dihydroxylations of 1-Substituted (E)- and (Z)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished

  摘要：

  Asymmetric dihydroxylations ("ADs") of the pentenynyl chlorides (E)- and (Z)-1 or the pentenyne-based ester (Z)-3 in the presence of (DHQ)(2)-containing ligands delivered diol stereoisomers (2R,3S)-2, (2R,3R)-2, and (3S,4R)-4, respectively. The ADs of pentenynyl ethers (E)-10 and (Z)-12, respectively, have the same stereochemical preference under analogous conditions; these reattributions correct previous reports of the contrary. The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.

  DOI：

  10.1021/ol103063t

文献信息

• Asymmetric Dihydroxylations of 1-Substituted (<i>E</i>)- and (<i>Z</i>)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished
  作者：Heike Burghart-Stoll、Oliver Böhnke、Reinhard Brückner

  DOI：10.1021/ol103063t

  日期：2011.3.4

  Asymmetric dihydroxylations ("ADs") of the pentenynyl chlorides (E)- and (Z)-1 or the pentenyne-based ester (Z)-3 in the presence of (DHQ)(2)-containing ligands delivered diol stereoisomers (2R,3S)-2, (2R,3R)-2, and (3S,4R)-4, respectively. The ADs of pentenynyl ethers (E)-10 and (Z)-12, respectively, have the same stereochemical preference under analogous conditions; these reattributions correct previous reports of the contrary. The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.