dimethyl (1R*,3R*,4S*,6S*)-7-oxabicyclo[4.1.0]heptane-cis-3,4-dicarboxylate | 121787-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: dimethyl (1R*,3R*,4S*,6S*)-7-oxabicyclo[4.1.0]heptane-cis-3,4-dicarboxylate
• 英文别名: (+/-)-(1R*,2S*,4S*,5R*)-dimethyl 4,5-epoxy-1,2-cyclohexanedicarboxylate；dimethyl 7-oxabicyclo[4.1.0]heptane-cis-3,4-dicarboxylate；dimethyl (1R,3R,4S,6S)-7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate
• CAS: 121787-39-1
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: OBOPQSIGGSCTEL-KVFPUHGPSA-N

物化性质

• 熔点：
  50-51 °C
• 沸点：
  298.8±30.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (1R*,3R*,4S*,6S*)-7-oxabicyclo[4.1.0]heptane-cis-3,4-dicarboxylate 在 硫酸 、 水 作用下， 以83%的产率得到dimethyl (1S*,2R*,4R*,5R*)-4,5-dihydroxycyclohexane-1,2-dicarboxylate
  参考文献：
  名称：

  Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids

  摘要：

  Glycosidases are very important enzymes involved in a variety of biochemical processes with a special importance to biotechnology, food industry, and pharmacology. Novel structurally simple inhibitors derived from cyclohexane-1,2-dicarboxylic acids were synthesized and tested against several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. The presence of at least two carboxylic groups and one hydroxy group was essential for efficient inhibition. Significant selective inhibition was observed for alpha- and beta-glucosidases, the magnitude of which depended on the configuration of substituents; inhibition increased for p-glucosidase by lengthening the alkoxy group of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.11.009
• 作为产物：
  描述：

  马来酸二甲酯 在 葡萄糖 、 cytochrome P₄₅₀ monooxygenase from Bacillus megaterium 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. phosphate buffer 为溶剂， 反应 20.0h， 生成 dimethyl (1R*,3R*,4S*,6S*)-7-oxabicyclo[4.1.0]heptane-cis-3,4-dicarboxylate
  参考文献：
  名称：

  A diastereoselective P450-catalyzed epoxidation reaction: anti versus syn reactivity

  摘要：

  The achiral cyclohexene derivative dimethyl cis-1,2,3,6-tetrahydrophthalate has been subjected to oxidation catalyzed by cytochrome P450 monooxygenase P450-BM3, leading to diastereoselective epoxidation rather than oxidative hydroxylation. This reaction occurs with 94% diastereoselectivity in favor of the anti-epoxide, in contrast to m-CPBA which delivers unselectively a 70:30 mixture of anti/syn diastereomers. The experimental results are nicely explained on a molecular level by docking experiments and molecular dynamics computations. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.03.076

文献信息

• Convenient synthesis of 1,3-dithiolane-2-thiones: cyclic trithiocarbonates as conformational locks
  作者：Irina A. Dotsenko、Qinliang Zhao、Andreas H. Franz、Patrick Batoon、Nataliya M. Samoshina、Vyacheslav V. Samoshin

  DOI：10.3998/ark.5550190.p008.671

  日期：——

  A series of novel 1,3-dithiolane-2-thiones, or cyclic trithiocarbonates, has been prepared by a new simple procedure: a treatment of the corresponding epoxides with the commercially available potassium ethyl xanthogenate, KSC(S)OEt. The stereochemistry of the products was determined by H NMR and in some cases by single-crystal X-ray data. Cyclohexane-based 1,3dithiolane-2-thiones revealed a trans-fusion

  一系列新的 1,3-dithiolane-2-thiones 或环状三硫代碳酸酯已通过一种新的简单程序制备：用市售的乙基黄原酸钾 KSC(S)OEt 处理相应的环氧化物。产物的立体化学由 H NMR 确定，在某些情况下由单晶 X 射线数据确定。基于环己烷的 1,3dithiolane-2-thiones 揭示了碳环和杂环的转化。从单取代的环己烯氧化物获得的产物证明了取代基的轴向位置。因此，环氧化物转化为三硫代碳酸酯可用作锁定不稳定构象的环状化合物的方法。
• Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols
  作者：Ke-Yin Ye、Terry MCallum、Song Lin

  DOI：10.1021/jacs.9b04993

  日期：2019.6.19

  exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti

  有机自由基通常是具有异常高反应性的短寿命中间体。从战略上讲，实现由有机自由基介导的合成有用的转化需要有效的引发和选择性终止事件。在这里，我们报告了一种新的催化策略，即双金属自由基氧化还原继电器，用于环氧化物向烯丙醇的区域和立体选择性重排。这种方法利用了 Ti 和 Co 配合物的丰富氧化还原化学，并将还原性环氧化物开环（引发）与氢原子转移（终止）相结合。至关重要的是，在影响关键的成键和断裂事件时，Ti 和 Co 催化剂彼此进行质子转移/电子转移以实现周转，从而构成真正协同的双催化系统。
• Novel 1,2,3-triazole compounds: Synthesis, In vitro xanthine oxidase inhibitory activity, and molecular docking studies
  作者：Ayse Tan

  DOI：10.1016/j.molstruc.2020.128060

  日期：2020.7

  study, novel 1,2,3-triazole compounds containing carbasugar frameworks (5 and 6) were synthesized by the copper-catalyzed azide-alkyne cycloaddition reactions and their in vitro inhibition effects on the enzyme xanthine oxidase were investigated. All of the synthesized compounds were characterized by spectroscopic methods. According to the enzyme inhibition results, compounds 5 (IC50 = 0.586 ± 0.017 μM)

  摘要 本研究通过铜催化的叠氮-炔环加成反应合成了含碳糖骨架（5和6）的新型1,2,3-三唑化合物，并研究了它们对黄嘌呤氧化酶的体外抑制作用。所有合成的化合物均通过光谱方法表征。根据酶抑制结果，化合物5（IC50 = 0.586 ± 0.017 μM）和化合物6（IC50 = 0.751 ± 0.021 μM）的抑制作用强于抑制作用的标准药物别嘌呤醇（IC50 = 1.143 ± 0.019 μM）黄嘌呤氧化酶。基于分子对接研究解释了 1,2,3-三唑化合物（5 和 6）与黄嘌呤氧化酶活性位点的结合模式。分子对接研究表明，芳香结构，
• Stereoselective hydrolysis of the dimethyl 4,5-epoxy-1,2-cis-cyclohexanedicar☐ylates with pig liver esterase (PLE)
  作者：Thomas Kuhn、Christoph Tamm、Andreas Riesen、Margareta Zehnder

  DOI：10.1016/s0040-4039(01)80284-7

  日期：——

  The behaviour of dimethyl cis- and trans-4,5-epoxy-cis-1,2-cyclohexanedicar☐ylate towards pig liver esterase (PLE) was studied. (1R, 2S, 4S, 5S)-4-Hydroxy-7-oxo-6-oxabicyclo[3.2.1]-octane-2-car☐ylic acid was formed.

  研究了顺式和反式4,5-环氧-顺式-1,2-环己烷二甲酸二甲酯对猪肝酯酶（PLE）的行为。形成（1R，2S，4S，5S）-4-羟基-7-氧代-6-氧杂双环[3.2.1]-辛烷-2-car☐羟基酸。
• Stereoselective epoxidation of cyclic alkenes using m-CPBA and Oxone®/trifluoroacetone — A comparison
  作者：Simon E. de Sousa、Peter O'Brien、Christopher D. Pilgram、Daniel Roder、Timothy D. Towers

  DOI：10.1016/s0040-4039(98)02320-x

  日期：1999.1

  A comparison of the observed diastereoselectivity of epoxidation of cyclic alkenes using m-CPBA and Oxone®/trifluoroacetone is reported. The results indicate that dioxirane epoxidations are sterically controlled and provide a crude model for determination of whether hydrogen bonding is operating in the m-CPBA epoxidations.

  使用环状烯烃的环氧化的非对映选择性观察的比较米报道-CPBA和的冰冷/三氟丙酮。结果表明，二环氧乙烷环氧化是空间控制的，并提供了用于确定氢键是否在m -CPBA环氧化中起作用的粗略模型。