(+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one | 55164-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one
• 英文别名: 5-hydroxy-7-oxabicyclo-[4.1.0(1,6)]hept-3-ene-2-one；(1S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 55164-61-9；55221-05-1；133965-31-8；143563-40-0
• 化学式: C₆H₆O₃
• 分子量: 126.112
• InChiKey: HHEPZGQHWOPVMS-PQLUHFTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one 在 水 作用下， 反应 96.0h， 以41%的产率得到4,5,6-trihydroxycyclohex-2-ene-1-one
  参考文献：
  名称：

  Synthesis of polyhydroxylated cyclohexenyl sulfides and sulfoxides. Evaluation of their inhibitory activity on α- and β-d-glucosidases

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(99)00137-8
• 作为产物：
  描述：

  (1R,2S,4S,6S,7R,8R,9S)-7-hydroxy-5-oxatetracyclo[7.2.1.02,8.04,6]dodec-10-en-3-one 以 二苯醚 为溶剂， 反应 2.0h， 以80%的产率得到(+/-)-(1α,5α,6α)-5-hydroxy-7-oxabicyclo<4.1.0>hept-3-en-2-one
  参考文献：
  名称：

  通过内消旋二酮的 Noyori 去对称化高效、可扩展的不对称合成环氧醌醇。

  摘要：

  通过 Noyori 转移氢化去对称化处理现成的内消旋环氧二酮 4，以多克规模制备了环氧醌醇 1a。尽管去对称化的固有对映选择性适中（82:18 er，转化率为 4%），但它是一种高度对映纯的产物（ 99.6:0.4 er) 可以在一次操作中获得 44% 的收率，通过在较长的反应时间 (48 小时) 下对次要对映异构体进行动力学拆分，或者通过与 93:7 er 混合物的酶促拆分相结合，以 73% 的收率获得。

  DOI：

  10.1016/j.tetasy.2011.04.022

文献信息

• Dienes as chiral templates: easy access to pure (2S,3S,4R)-4-hydroxy-2,3-epoxycyclohex-5-en-1-one
  作者：Antony Mauvais、Ekkehard Winterfeldt

  DOI：10.1016/s0040-4020(01)87948-5

  日期：1993.6

  The title compound 6 was obtained stereospecifically through a concise sequence including a Diels-Alder reaction with the chiral diene 2 and the retro reaction. The Favorskii rearrangement starting from the intermediate epoxide 4 was found to be regioselective.

  标题化合物6是通过包括与手性二烯2的Diels-Alder反应和逆反应的简明序列立体定向获得的。发现从中间环氧化物4开始的Favorskii重排是区域选择性的。
• Cambie, Richard C.; Renner, Noel D.; Rutledge, Peter S., Australian Journal of Chemistry, 1991, vol. 44, p. 61 - 75
  作者：Cambie, Richard C.、Renner, Noel D.、Rutledge, Peter S.、Woodgate, Paul D.

  DOI：——

  日期：——
• The synthesis of epi-epoxydon utilising the Baylis–Hillman reaction
  作者：Thorsten Genski、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(02)00529-4

  日期：2002.5

  -(+/-)-epi-Epoxydon was synthesised by means of a triethylaluminium/ tri-n-butylphosphine-catalysed Baylis-Hillman reaction between an O-protected epoxidised hydroxyquinol core and paraformaldehyde, constituting the first application of the Baylis-Hillman reaction to a highly functionalised beta-substituted enone. (C) 2002 Elsevier Science Ltd. All rights reserved.