5-cyclooctene-1,2-diol | 55519-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-cyclooctene-1,2-diol
• 英文别名: rac-(Z)-cyclooct-5-en-1,2-diol；(Z)-cyclooct-5-ene-1,2-diol；cyclooctene-5,6-diol；(5Z)-cyclooct-5-ene-1,2-diol
• CAS: 55519-21-6
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: JWEYNDRAHPIRPI-UPHRSURJSA-N

物化性质

• 沸点：
  233.5±40.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-cyclooctene-1,2-diol 在 sodium periodate 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.5h， 生成 (Z)-oct-4-enedial
  参考文献：
  名称：

  用 [Fe(OTf)2(mix-BPBP)] 和 H2O2 和 NaIO4 的组合将二烯中的富电子双键区域选择性裂解为羰基化合物

  摘要：

  已经开发了一种将二烯区域选择性转化为羰基化合物的方法。富电子烯烃选择性反应产生有价值的醛和酮。该方法基于催化剂 [Fe(OTf)2(mix-BPBP)] 和 H2O2（1.0 当量）和 NaIO4（1.5 当量）的氧化剂组合；它使用温和的条件和较短的反应时间，优于其他烯烃裂解方法。铁基催化剂 [Fe(OTf)2(mix-BPBP)] 与氧化剂 H2O2 和 NaIO4 的组合可以区分电子不同的双键，并氧化裂解二烯中的富电子键，生成醛和酮以区域选择性的方式。该反应需要温和的条件 (0-50 C) 和较短的反应时间 (70 分钟)。

  DOI：

  10.1002/ejic.201500213
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 在 cethyltrimethylammonium permanganate 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到5-cyclooctene-1,2-diol
  参考文献：
  名称：

  Permanganate ion oxidations. 19. Hexadecyltrimethylammonium permanganate oxidation of cycloalkenes

  摘要：

  DOI：

  10.1021/jo00272a051

文献信息

• IMIDAZOLIDINE-BASED METAL CARBENE METATHESIS CATALYSTS
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20160237101A9

  公开（公告）日：2016-08-18

  The present invention relates to novel metathesis catalysts with an imidazolidine-based ligand and to methods for making and using the same. The inventive catalysts are of the formula wherein: M is ruthenium or osmium; X and X 1 are each independently an anionic ligand; L is a neutral electron donor ligand; and, R, R 1 , R 6 , R 7 , R 8 , and R 9 are each independently hydrogen or a substituent selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, aryl, C 1 -C 20 carboxylate, C 1 -C 20 alkoxy, C 2 -C 20 alkenyloxy, C 2 -C 20 alkynyloxy, aryloxy, C 2 -C 20 alkoxycarbonyl, C 1 -C 20 alkylthiol, aryl thiol, C 1 -C 20 alkylsulfonyl and C 2 -C 20 alkylsulfinyl, the substituent optionally substituted with one or more moieties selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 alkoxy, aryl, and a functional group selected from the group consisting of hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, carbamate, and halogen. The inclusion of an imidazolidine ligand to the previously described ruthenium or osmium catalysts has been found to dramatically improve the properties of these complexes. The inventive catalysts maintains the functional group tolerance of previously described ruthenium complexes while having enhanced metathesis activity that compares favorably to prior art tungsten and molybdenum systems.

  本发明涉及一种新型的以咪唑啉为基础的配体的交换催化剂以及其制备和使用方法。该创新催化剂的化学式为：其中，M为钌或锇；X和X1分别为独立的阴离子配体；L为中性电子供体配体；R、R1、R6、R7、R8和R9分别为氢或选自以下基团的取代基：C1-C20烷基、C2-C20烯基、C2-C20炔基、芳基、C1-C20羧酸酯、C1-C20烷氧基、C2-C20烯氧基、C2-C20炔氧基、芳氧基、C2-C20烷氧羰基、C1-C20烷基硫醇、芳基硫醇、C1-C20烷基磺酰基和C2-C20烷基亚磺酰基，所述取代基可选地被一个或多个选自以下基团的取代基所取代：C1-C10烷基、C1-C10烷氧基、芳基和羟基、硫醇、硫醚、酮、醛、酯、醚、胺、亚胺、酰胺、硝基、羧酸、二硫化物、碳酸酯、异氰酸酯、碳酸酰基、卡波酯、卡巴酰胺和卤素的官能团。在以前所述的钌或锇催化剂中加入咪唑啉配体被发现可以显著改善这些配合物的性质。这种创新催化剂保持了以前所描述的钌配合物的官能团耐受性，同时具有增强的交换活性，与先前的钨和钼系统相比具有更好的性能。
• Microwave-Assisted Kinetic Resolution of Homochiral (Z)-Cyclooct-5-ene-1,2-diol and (Z)-2-Acetoxycyclooct-4-enyl Acetate Using Lipases
  作者：Hervé Rouillard、Emmanuel Deau、Lisianne Domon、Jean-René Chérouvrier、Marianne Graber、Valérie Thiéry

  DOI：10.3390/molecules19079215

  日期：——

  Over the last decade, the use of biocatalysts has become an attractive alternative to conventional chemical methods, especially for organic synthesis, due to their unusual properties. Among these enzymes, lipases are the most widely used, because they are cheap, easily available, cofactor-free, and have broad substrate specificity. Combined to microwave heating in non-aqueous medium, recent results suggest that irradiation may influence the enzyme activity. This Communication reports the benefits of lipases and the microwave irradiation on the kinetic resolution of racemic homochiral (Z)-cyclooct-5-ene-1,2-diol and (Z)-2-acetoxycyclooct-4-enyl acetate. In order to best achieve the kinetic resolution, different parameters were studied including the type of lipase, the temperature, the impact of microwave power compared to conventional heating. Optimization of the reaction parameters lead to the obtainment of highly enriched or enantiopure diols and diesters in a clean, efficient and safe way.

  在过去十年中，由于生物催化剂的特殊性质，使用生物催化剂已成为传统化学方法的一种有吸引力的替代方法，特别是在有机合成方面。在这些酶中，脂肪酶的应用最为广泛，因为它们价格便宜、容易获得、不含辅助因子，而且具有广泛的底物特异性。最近的研究结果表明，在非水介质中结合微波加热，辐照可能会影响酶的活性。本通讯报告了脂肪酶和微波辐照对外消旋同手性(Z)-环辛烯-5-烯-1,2-二醇和(Z)-2-乙酰氧基环辛烯-4-烯基乙酸酯动力学解析的益处。为了最好地实现动力学解析，研究了不同的参数，包括脂肪酶的类型、温度、微波功率与传统加热相比的影响。通过优化反应参数，以清洁、高效和安全的方式获得了高富集度或对映纯的二元醇和二酯。
• Concentrated, stable, preferably clear, fabric softening composition
  申请人：Trinh Toan

  公开号：US20060058216A1

  公开（公告）日：2006-03-16

  Principal solvents, especially mono-ol and diol principal solvents, having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, are disclosed that have the ability to make clear aqueous fabric softener compositions containing relatively high concentrations of fabric softener actives having ester linkages in their long, hydrophobic chains. The fabric softener actives are either unsaturated, or have intermediate length chains (˜C 12-14 ) and the said principal solvents are used at levels of less than about 40%. Other solvents may be present. Some of the said principal solvents are novel compounds and/or novel mixtures. Premixes of the fabric softening actives, the principal solvents, and, optionally, other solvents are useful in the preparation of complete formulations by obviating/limiting the need for heating.

  本发明揭示了主要溶剂，特别是具有ClogP约为0.15至约0.64，优选为约0.25至约0.62，更优选为约0.40至约0.60的单醇和双醇主要溶剂，具有制备含有长链疏水基中酯键的相对高浓度织物柔顺剂活性成分的清澈水性织物柔顺剂组合物的能力。织物柔顺剂活性成分可以是不饱和的，也可以具有中等长度的链（约C12-14），所述主要溶剂的使用水平小于约40％。其他溶剂可以存在。其中一些主要溶剂是新化合物和/或新混合物。织物柔顺剂活性成分、主要溶剂和可选的其他溶剂的预混物在制备完整配方时是有用的，因为它们可以避免/限制加热的需要。
• Concentrated, stable fabric softening composition
  申请人：——

  公开号：US20030153483A1

  公开（公告）日：2003-08-14

  Principal solvents, especially mono-ol and diol principal solvents, having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, are disclosed that have the ability to make clear aqueous fabric softener compositions containing relatively high concentrations of fabric softener actives having ester linkages in their long, hydrophobic chains. The fabric softener actives are either unsaturated, or have intermediate length chains (˜C 12-14 ) and the said principal solvents are used at levels of less than about 40%. Other solvents may be present. Some of the said principal solvents are novel compounds and/or novel mixtures. Premixes of the fabric softening actives, the principal solvents, and, optionally, other solvents are useful in the preparation of complete formulations by obviating/limiting the need for heating.

  本发明涉及主要溶剂，特别是具有从约0.15到约0.64的ClogP值的单醇和二醇主要溶剂，优选从约0.25到约0.62，更优选从约0.40到约0.60，具有使含有长的亲水性链中的酯键的织物柔软剂活性成分相对高浓度的清澈水性织物柔软剂组合物的能力。织物柔软剂活性成分可以是不饱和的，也可以具有中等长度的链（约C12-14），所述主要溶剂的使用水平低于约40％。其他溶剂可能也存在。其中一些主要溶剂是新化合物和/或新混合物。织物柔软剂活性成分、主要溶剂和可选的其他溶剂的预混物可用于制备完整配方，从而避免/限制加热的需要。
• Closed-loop recycling of lignin-based sustainable polymers with an all-hydrocarbon backbone
  作者：Yuan Hu、Qiyi Ran、Siping Wei、Chengcheng Wang、Zhijing Wu、Enhua Xu、Zhenyang Luo、Puyou Jia、Ye Sha

  DOI：10.1039/d3gc01671d

  日期：——

  Sustainable polymers from biomass with a nonhydrolytic backbone are highly desirable because they meet performance requirements. However, their inert nature hinders chemical recycling under mild conditions. In this work, we report a series of recyclable lignin-based sustainable polymers with an all-hydrocarbon backbone showing excellent thermal stability (decomposition temperature up to 380 °C) and

  来自具有非水解主链的生物质的可持续聚合物是非常理想的，因为它们满足性能要求。然而，它们的惰性阻碍了温和条件下的化学回收。在这项工作中，我们报告了一系列可回收的木质素基可持续聚合物，其具有全烃主链，表现出优异的热稳定性（分解温度高达 380 °C）和可调的机械性能。这些由木质素制成的可再生聚烯烃可以在温和加热 (50 °C) 下使用格鲁布斯 II 催化剂在几分钟内解聚回原始单体，并具有定量 (>90%) 的回收率。这些聚烯烃是通过环辛烯与反式的开环复分解聚合（ROMP）制备的。-二氧戊环缩酮安装在5,6-位，木质素衍生物作为悬垂物。额外的稠合环将环辛烯单体的环应变能显着降低至~5.0 kcal mol -1，从而导致所得聚合物可解聚以建立闭环生命周期。