(S)-1-(2-iodo-3-methoxyphenyl)ethanol | 215316-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-(2-iodo-3-methoxyphenyl)ethanol
• 英文别名: (1S)-1-(2-iodo-3-methoxyphenyl)ethanol
• CAS: 215316-80-6
• 化学式: C₉H₁₁IO₂
• 分子量: 278.09
• InChiKey: YWKQFMBLZNKWNT-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-iodo-3-methoxyphenyl)ethanol 在 sodium perborate 、 sodium hydride 作用下， 反应 12.5h， 生成 (S)-bis(acetato-O)[2-(1-methoxyethyl)-6-methoxyphenyl]iodine
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x
• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-乙酮 在 盐酸 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 碘 、 (-)-diisopinocamphenylborane chloride 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 39.33h， 生成 (S)-1-(2-iodo-3-methoxyphenyl)ethanol
  参考文献：
  名称：

  New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

  摘要：

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.

  DOI：

  10.1021/jo980475x

文献信息

• New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis
  作者：Urs H. Hirt、Bernhard Spingler、Thomas Wirth

  DOI：10.1021/jo980475x

  日期：1998.10.1

  The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the alpha-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.