4,5,6-trihydroxycyclohex-2-ene-1-one | 89533-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6-trihydroxycyclohex-2-ene-1-one
• 英文别名: 4,5,6-trihydroxycyclohex-2-en-1-one；(+/-)-3-Oxo-cyclohexen-1-triol-(4t,5c,6t)；(4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one；(4S,5R,6S)-4,5,6-trihydroxycyclohex-2-en-1-one
• CAS: 89533-81-3；124096-72-6；124096-73-7
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: UDGPTYYVDNKAPG-OTWZMJIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5,6-trihydroxycyclohex-2-ene-1-one 在 吡啶 、 咪唑 、 正丁基锂 、 palladium 10% on activated carbon 、 5% palladium on barium sulphate 、 氢气 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、620.54 kPa 条件下， 反应 32.92h， 生成
  参考文献：
  名称：

  antascomicin B C21-C34 片段的合成

  摘要：

  使用 Ireland-Claisen 和烯丙基二氮烯重排制备有效的 FKBP12 结合大环内酯 antascomicin B 的 C21–C34 片段，分别建立 C26/C27 和 C23 立体中心。直接氢化安装了C29 β-构型。该片段拥有天然产物中包含的11 个固定立体中心中的7 个。

  DOI：

  10.1016/j.tetlet.2011.09.027
• 作为产物：
  描述：

  2-deoxy-scyllo-inosose 以 水 为溶剂， 反应 2.0h， 以as a result, (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one was obtained at a yield of 50%的产率得到4,5,6-trihydroxycyclohex-2-ene-1-one
  参考文献：
  名称：

  Method for producing catechol

  摘要：

  提供了一种通过在氢还原条件下加热反应(4S,5R,6S)-4,5,6-三羟基-2-环己烯-1-酮来制备邻苯二酚的单锅法。

  公开号：

  US08378146B2

文献信息

• METHOD FOR PRODUCING POLYHYDRIC PHENOL
  申请人：Kitagawa Hideo

  公开号：US20120046498A1

  公开（公告）日：2012-02-23

  The present invention is a method for producing a polyhydric phenol, including the following steps (a) to (d): (a) a first step of producing (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexcene- 1 -one from 2-deoxy-scyllo-inosose by a dehydration reaction; (b) a second step of producing 1,2,4-trihydroxybenzene from the (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene- 1 -one obtained in the first step by a dehydration reaction; (c) a third step of producing 4-hydroxycyclohexane-1,3-dione from the 1,2,4-trihydroxybenzene by a catalytic hydrogenation reaction with the use of a metal catalyst; and (d) a fourth step of producing hydroquinone by heating the 4-hydroxycyclohexane-1,3-dione.

  本发明涉及一种生产多羟基苯酚的方法，包括以下步骤（a）至（d）：（a）第一步，通过脱水反应从2-去氧-赤藓糖生成（4S，5R，6S）-4,5,6-三羟基-2-环己烯-1-酮；（b）第二步，通过脱水反应从第一步得到的（4S，5R，6S）-4,5,6-三羟基-2-环己烯-1-酮生成1,2,4-三羟基苯；（c）第三步，使用金属催化剂进行催化氢化反应，从1,2,4-三羟基苯生成4-羟基环己烷-1,3-二酮；（d）第四步，通过加热4-羟基环己烷-1,3-二酮生成对苯二酚。
• METHOD FOR PRODUCING CATECHOL
  申请人：Suzuki Tsuneji

  公开号：US20110034735A1

  公开（公告）日：2011-02-10

  Provided is a method for producing catechol in a one-pot by reacting (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one under hydrogen-reducing conditions while heating.

  提供了一种方法，通过在氢还原条件下加热反应(4S,5R,6S)-4,5,6-三羟基-2-环己烯-1-酮，以一锅法生产邻苯二酚。
• CATECHOL MANUFACTURING METHOD
  申请人：Mitsui Chemicals, Inc.

  公开号：EP2266940A1

  公开（公告）日：2010-12-29

  Provided is a method for producing catechol in a one-pot by reacting (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one under hydrogen-reducing conditions while heating.

  本发明提供了一种在氢还原条件下加热反应 (4S,5R,6S)-4,5,6-三羟基-2-环己烯-1-酮的单锅生产邻苯二酚的方法。
• EP2266940
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of polyhydroxylated cyclohexenyl sulfides and sulfoxides. Evaluation of their inhibitory activity on α- and β-d-glucosidases
  作者：André Lubineau、Isabelle Billault

  DOI：10.1016/s0008-6215(99)00137-8

  日期：1999.7

  Racemic polyhydroxylated sulfides and sulfoxides have been prepared as potential transition-state analogs of the glucoside hydrolysis reaction, through a reaction sequence involving transformations of a ketone group into thioacetal, followed by partial oxidation to sulfoxide then regioselective thermal elimination of the sulfoxide to vinyl sulfide. These sulfides with two, three or four hydroxyl groups have been oxidized to the corresponding diastereoisomeric sulfoxides. All compounds, summarily tested as inhibitors of alpha- and beta-glucosidases, were found to be very weak inhibitors and thus their biological properties were not studied in depth. Curiously, however, their inhibitory properties, which are in the 10 mM range, do not really depend upon the number of hydroxyl groups or upon the presence of polar sulfoxide. In order to get more insights, 2-phenyl sulfoxide-3,4,5-trihydroxycyclohex-1-ene (9a) was studied in more detail using Brewers yeast alpha-glucosidase and was shown to give a mixed-type inhibition with a high K-i of 45 mM. (C) 1999 Elsevier Science Ltd. All rights reserved.