tert-butyl ((2-oxo-1,3-dioxolan-4-yl)methyl)carbamate | 1418764-30-3

• 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: tert-butyl ((2-oxo-1,3-dioxolan-4-yl)methyl)carbamate
• 英文别名: tert-butyl N-[(2-oxo-1,3-dioxolan-4-yl)methyl]carbamate
• CAS: 1418764-30-3
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: FDTVOFSHQIIABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二氧化碳 、 N-(2-环氧乙烷基甲基)氨基甲酸酯 在 C₃₄H₄₁N₇NiO₂ 作用下， 以 neat (no solvent) 为溶剂， 130.0 ℃ 、2.0 MPa 条件下， 反应 18.0h， 生成 tert-butyl ((2-oxo-1,3-dioxolan-4-yl)methyl)carbamate
  参考文献：
  名称：

  由镍 (II) 的新型 N 稠合介离子卡宾配合物催化的 CO2 和环氧化物的偶联

  摘要：

  我们报告了通过分子内芬克尔斯坦环化级联反应合成两种具有咔唑骨架的刚性介离子卡宾 (MIC) 配体，并研究它们对乙酸镍 ( II )的配位行为。尽管镍 ( II ) 卡宾配合物4a、b在其化学成分上仅显示出微小的差异，但它们在化学性质（例如溶解度）方面表现出奇怪的差异。此外，还评估了这些新型 MIC 复合物在二氧化碳和环氧化物偶联中的潜力，以及与经典 NHC 衍生复合物相比的反应性差异。

  DOI：

  10.1039/d1dt03311e

文献信息

• Highly Efficient Organocatalyzed Conversion of Oxiranes and CO₂into Organic Carbonates
  作者：Sergio Sopeña、Giulia Fiorani、Carmen Martín、Arjan W. Kleij

  DOI：10.1002/cssc.201500710

  日期：2015.10

  A binary catalyst system based on tannic acid/NBu4X (X=Br, I) is presented as a highly efficient organocatalyst at very low catalyst loading for the coupling of carbon dioxide and functional oxiranes to afford organic carbonates in good yields. The presence of multiple polyphenol fragments within the tannic acid structure is considered to be beneficial for synergistic effects that lead to higher stabilization

  提出了基于单宁酸/ NBu 4 X（X = Br，I）的二元催化剂体系，它是一种非常低的催化剂负载量下的高效有机催化剂，用于二氧化碳和功能性环氧乙烷的偶联，以高收率提供有机碳酸酯。单宁酸结构内存在多个多酚片段被认为有利于协同作用，这种协同作用可在催化过程中提高催化剂结构的稳定性。观察到的周转频率（TOF）超过200 h -1，并且是迄今为止在该CO 2区域中有机催化剂报告的最高频率转换。对于迄今报道的大多数基于金属的催化剂体系，该有机催化剂体系提供了一种有用的，易于获得的，廉价的，尤其是反应性的替代品。
• A Powerful Aluminum Catalyst for the Synthesis of Highly Functional Organic Carbonates
  作者：Christopher J. Whiteoak、Nicola Kielland、Victor Laserna、Eduardo C. Escudero-Adán、Eddy Martin、Arjan W. Kleij

  DOI：10.1021/ja311053h

  日期：2013.1.30

  An aluminum complex based on an amino triphenolate ligand scaffold shows unprecedented high activity (initial TOFs up to 36 000 h(-1)), broad substrate scope, and functional group tolerance in the formation of highly functional organic carbonates prepared from epoxides and CO2. The developed catalytic protocol is further characterized by low catalyst loadings and relative mild reaction conditions using a cheap, abundant, and nontoxic metal.
• CO₂ Adducts of Phosphorus Ylides: Highly Active Organocatalysts for Carbon Dioxide Transformation
  作者：Hui Zhou、Guo-Xu Wang、Wen-Zhen Zhang、Xiao-Bing Lu

  DOI：10.1021/acscatal.5b01409

  日期：2015.11.6

  A series of phosphorus ylide (P-ylide) CO2 adducts were synthesized and first used as organocatalysts for CO2 transformation. Detailed studies on the cycloaddition reaction of CO2 with terminal epoxides show that P-ylide CO2 adducts are efficient metal-free and halogen-free organocatalysts to mediate this reaction under ambient conditions (25 degrees C, 1 atm of CO2). More importantly, the reactions proceeded with a broad scope, high efficiency, and good functional group tolerance and the corresponding cyclic carbonate products were obtained in good to excellent yields (46-99%). Meanwhile, the kinetic study by in situ FTIR methods suggested an intermolecular cooperation effect for effectively accelerating the ring opening of terminal epoxides. Furthermore, from an investigation of the catalytic diversity of P-ylide CO2 adducts, CO2 also could be converted to functionalized cyclic alpha-alkylidene carbonates, oxazolidinone, and N-methylated and N-formylated amines by organocatalytic reactions.