o-carboranyl-(4-hydroxymethylphenyl)methanol | 186751-94-0

• 英文名称: o-carboranyl-(4-hydroxymethylphenyl)methanol
• CAS: 186751-94-0
• 化学式: C₁₀H₂₀B₁₀O₂
• 分子量: 280.378
• InChiKey: FLXJXIRVLSZNPC-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• sp3杂化的碳原子比例：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  o-carboranyl-(4-methoxycarbonylphenyl)methanol 、 lithium aluminium tetrahydride 以 四氢呋喃 为溶剂， 以95%的产率得到o-carboranyl-(4-hydroxymethylphenyl)methanol
  参考文献：
  名称：

  Synthetic utility of o-carborane: novel protective group for aldehydes and ketones

  摘要：

  o-Carborane acts as a novel protective group of carbonyl compounds. The reaction of lithiocarborane 2, which was prepared in an essentially quantitative yield from o-carborane and n-butyllithium, with aldehydes or ketones 1 gave the corresponding addition products, o-carboranyl methanol derivatives 3, in high yields. Cleavage of o-carborane from 3 was carried out by treating 3 with catalytic amounts of KOH in THF/H2O (100/1), giving the corresponding aldehydes or ketones in good to high yields along with recovered o-carborane. Accordingly, o-carborane may be utilized as a protective group stable under protic and Lewis acid conditions. Selective alkylation of an ester group, selective reduction of an ester, and selective alkylation of a ketone in the presence of an aldehyde are accomplished by using o-carborane protective groups. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00922-x