6-hydroxy-diosphenol | 71843-50-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6-hydroxy-diosphenol
• 英文别名: 1-p-menthene-2,4-diol-3-one；2-Cyclohexen-1-one, 2,6-dihydroxy-3-methyl-6-(1-methylethyl)-；2,6-dihydroxy-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
• CAS: 71843-50-0
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: DMSLPCPZNHHRMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2-羟基-3-(异丙基)-6-甲基环己-2-烯-1-酮 在 sodium hydride 、 二甲基二环氧乙烷 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 36.5h， 以65%的产率得到6-hydroxy-diosphenol
  参考文献：
  名称：

  SYNTHESIS OF NATURALLY OCCURRING DIOSPHENOLS AND HYDROXYDIOSPHENOLS

  摘要：

  Syntheses of diosphenol (3), psi-diosphenol (4), 6-hydroxydiosphenol (5) and 6-hydroxy- psi-diosphenol (6), which are constituents of the essential oil from Barosma betulina Bard. (mountain buchu), are discussed.

  DOI：

  10.1081/scc-120003623

文献信息

• The Transformations of Terpene Eetones by Oxygen. II. The Base-catalyzed Autoxidation of Pulegone and Fukinone and Their Dihydro Compounds
  作者：Akio Horinaka、Eiyu Yo、Otoji Mori、Keizo Naya

  DOI：10.1246/bcsj.52.2372

  日期：1979.8

  Upon autoxidation in alkaline media, pulegone and fukinone (2) gave pairs of hydroxy ketones respectively as the major products; also, hydroxyeremophilone was isolated as its acetate from 2. On the other hand, their dihydro compounds afforded hydroxy ketones, diosphenols, and acids.

  在碱性介质中自氧化时，普尔根和富基酮（2）分别生成一对羟基酮作为主要产物；此外，还从2中分离得到了羟基埃瑞莫菲酮的醋酸酯。另一方面，它们的二氢化合物则产生了羟基酮、二氧苯酚和酸。
• 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.
• Oxidative cleavage of the C–C bond of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha
  作者：Yoshitomo Matsuura、Wen Chai、Etsuko Endoh、Jyumpei Suhara、Hiroki Hamada、C.Akira Horiuchi

  DOI：10.1016/s0031-9422(02)00373-4

  日期：2002.11

  Biotransformation of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha involves regioselective oxidative cleavage of the C-C bond to give the corresponding oxocarboxylic acids shortened by one carbon unit. In the case of cyclohexane-1,2-dione, adipic acid was obtained. (C) 2002 Elsevier Science Ltd. All rights, reserved.
• 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.