(R,R)-hexahydrobenzo-1,3-dioxo-2-one | 191939-13-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (R,R)-hexahydrobenzo-1,3-dioxo-2-one
• 英文别名: trans-cyclohexene carbonate；(R,R)-trans-1,2-cyclohexene carbonate；trans-1,2-Cyclohexandiol-carbonat；trans-Cyclohexan-1,2-diyl-carbonat；(3aR,7aR)-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-2-one
• CAS: 191939-13-6
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: WQVFVJFUDNRICW-PHDIDXHHSA-N

物化性质

• 沸点：
  298.8±9.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,R)-hexahydrobenzo-1,3-dioxo-2-one 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 Piperidine-1,4-dicarboxylic acid mono-[(1R,2R)-2-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl] ester
  参考文献：
  名称：

  PIPERIDINE CARBOXYLIC ACID DERIVATIVES AS SIALYL LEWIS X MIMETICS

  摘要：

  Four piperidine carboxylic acid derivatives designed as mimetics of the sialyl Lewis X determinant were synthesized. Their inhibitory potency for selectin mediated cell adhesion was evaluated in cell culture assays, in viva and in a reperfusion model. Compound 7 showed strong inhibition of leukocyte adhesion in rats and a poweful decrease of the incidence of arrhythmias in a reperfusion model in isolated rabbit hearts. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00213-8
• 作为产物：
  描述：

  二氧化碳 、 氧化环己烯 在 双(三苯基正膦基)氯化铵 作用下， 80.0 ℃ 、2.03 MPa 条件下， 反应 48.0h， 以16.9%的产率得到(R,R)-hexahydrobenzo-1,3-dioxo-2-one
  参考文献：
  名称：

  通过可切换催化一锅法精密合成 AB、ABA 和 ABC 嵌段共聚物

  摘要：

  通过简单的技术精确合成具有分子复杂性的定义明确的嵌段共聚物一直是一项有意义但很少能实现的任务。在这里，报告了一种商业可切换催化剂，包括一个微妙的“双切换”过程。这种独特的开关可以应用于五组分混合物以制备序列控制的 AB、ABA 和 ABC 共聚物。

  DOI：

  10.1002/anie.202117533

文献信息

• Manganese‐Catalyzed Hydroborations with Broad Scope
  作者：Pradip Ghosh、Axel Jacobi von Wangelin

  DOI：10.1002/anie.202103550

  日期：2021.7.12

  synthetic manipulation and chemical valorization. The applications of catalytic hydrofunctionalization benefit from the use of liquid reducing agents and operationally facile setups. Metal-catalyzed hydroborations provide a highly prolific platform for reductive valorizations of stable C=X electrophiles. Here, we report an especially facile, broad-scope reduction of various functions including carbonyls

  容易获得的氧化物质的还原转化是合成操作和化学价值化的核心。催化加氢官能化的应用受益于液体还原剂的使用和操作简便的设置。金属催化的硼氢化反应为稳定的 C=X 亲电试剂的还原增值提供了一个高产的平台。在这里，我们报告了在非常温和的条件下，使用廉价的预催化剂 Mn(hmds) 2可以特别轻松、广泛地还原各种功能，包括羰基化合物、羧酸盐、吡啶、碳二亚胺和碳酸盐。该反应可以成功地应用于解聚。
• Reduction of Cyclic and Linear Organic Carbonates Using a Readily Available Magnesium Catalyst
  作者：Marcin Szewczyk、Marc Magre、Viktoriia Zubar、Magnus Rueping

  DOI：10.1021/acscatal.9b04086

  日期：2019.12.6

  Efficient reduction of cyclic and linear organic carbonates catalyzed by a readily available earth alkaline catalyst has been achieved. The described homogenous reaction based on a ligand-free magnesium catalyst provides an indirect route for the conversion of CO2 into valuable alcohols. The reaction proceeds with high yields under mild reaction conditions, with low catalyst loading and short reaction times

  已经实现了通过容易获得的碱土金属催化剂催化的环状和线性有机碳酸酯的有效还原。所述基于无配体的镁催化剂的均相反应提供了将CO 2转化为有价值的醇的间接途径。该反应在温和的反应条件下以高收率进行，催化剂用量低，反应时间短，并且对各种线性和环状碳酸酯具有广泛的适用性。另外，它可用于聚碳酸酯的解聚。
• Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols
  作者：Christian E. Müller、Daniela Zell、Radim Hrdina、Raffael C. Wende、Lukas Wanka、Sören M. M. Schuler、Peter R. Schreiner

  DOI：10.1021/jo401195c

  日期：2013.9.6

  Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.
• PATRONI, JOSEPH J.;STICK, ROBERT V., AUSTRAL. J. CHEM., 40,(1987) N 5, 795-802
  作者：PATRONI, JOSEPH J.、STICK, ROBERT V.

  DOI：——

  日期：——
• PROCESS FOR PREPARING POLYCARBONATES BY POLYMERIZATION OF FIVE-MEMBERED-RING CYCLIC CARBONATES
  申请人：Total Research & Technology Feluy

  公开号：EP2992032B1

  公开（公告）日：2017-12-06