4,6-dihydroxy-5-nonanone | 649767-30-6

• 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: 4,6-dihydroxy-5-nonanone
• 英文别名: 4,6-Dihydroxynonan-5-one
• CAS: 649767-30-6
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: HHCANUABVUIWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  meso-4,6-diiodo-5-nonanone 在 三乙胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以65%的产率得到4,6-dihydroxy-5-nonanone
  参考文献：
  名称：

  A novel synthesis of α-hydroxy- and α,α′-dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation

  摘要：

  A novel reaction of alpha-iodo ketone (alpha-iodocycloalkanone, alpha-iodo-beta-alkoxy ester, and alpha-iodoacyclicketone) with irradiation under a high-pressure mercury lamp gave the corresponding alpha-hydroxyketone in good yields. In the case of alpha,alpha'-diiodo ketone, alpha,alpha'-dihydroxyketone which little has been reported until now was obtained. This reaction affords a new, clean and convenient synthetic method for alpha-hydroxy- and alpha,alpha'-dihydroxyketone. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.082

文献信息

• A novel synthesis of α-hydroxy- and α,α′-dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation
  作者：C.Akira Horiuchi、Akinori Takeda、Wen Chai、Kishoh Ohwada、Shun-Jun Ji、T.Tomoyoshi Takahashi

  DOI：10.1016/j.tetlet.2003.10.082

  日期：2003.12

  A novel reaction of alpha-iodo ketone (alpha-iodocycloalkanone, alpha-iodo-beta-alkoxy ester, and alpha-iodoacyclicketone) with irradiation under a high-pressure mercury lamp gave the corresponding alpha-hydroxyketone in good yields. In the case of alpha,alpha'-diiodo ketone, alpha,alpha'-dihydroxyketone which little has been reported until now was obtained. This reaction affords a new, clean and convenient synthetic method for alpha-hydroxy- and alpha,alpha'-dihydroxyketone. (C) 2003 Elsevier Ltd. All rights reserved.
• CRANDALL, JACK K.;BATAL, DAVID J.;SEBESTA, DAVID P.;LIN, FENG, J. ORG. CHEM., 56,(1991) N, C. 1153-1166
  作者：CRANDALL, JACK K.、BATAL, DAVID J.、SEBESTA, DAVID P.、LIN, FENG

  DOI：——

  日期：——
• Carbostyril compounds, compositions containing same and processes for preparing same
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0052016B1

  公开（公告）日：1984-09-05
• Photo-irradiation of α-halo carbonyl compounds: a novel synthesis of α-hydroxy- and α,α′-dihydroxyketones
  作者：Wen Chai、Akihiro Takeda、Makoto Hara、Shun-Jun Ji、C. Akira Horiuchi

  DOI：10.1016/j.tet.2005.01.010

  日期：2005.2

  The reaction of g.-halo ketones (alpha-iodocycloalkanones, alpha-bromocycloalkanones, alpha-iodo-beta-alkoxy esters, and alpha-iodoacyclic-ketones) with irradiation under a high-pressure mercury lamp gave the corresponding alpha-hydroxyketones in good yields. For alpha-bromoketones, it was found that alpha-hydroxylation does not occur. However, alpha-bromoketones were convened into a-hydroxyketones in the presence of KI. In the case of alpha,alpha(1)-diiodo ketones, alpha,alpha(1)-dihydroxyketones, which up to now have scarcely been reported, were obtained. This reaction affords a new, clean and convenient synthetic method for alpha-hydroxy- and alpha,alpha(1)-dihydroxyketones. (C) 2005 Elsevier Ltd. All rights reserved.