1-叔丁基-1-乙基-3-苯基脲 | 1202047-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-叔丁基-1-乙基-3-苯基脲
• 英文名称: 1-tert-butyl-1-ethyl-3-phenylurea
• CAS: 1202047-15-1
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: DRLWRFBYXCZWFC-UHFFFAOYSA-N

物化性质

• 熔点：
  75-77 °C
• 沸点：
  366.6±15.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-叔丁基-1-乙基-3-苯基脲 在 水 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以99%的产率得到双苯基脲
  参考文献：
  名称：

  作为掩蔽异氰酸酯的受阻尿素：中性条件下亲核试剂的轻松氨基甲酰化

  摘要：

  越大越好：空间受阻的二烷基脲以比受阻较小的对应物快得多的速率进行亲核取代（参见方案）。中间体异氰酸酯形成时的空间减压可以解释这种违反直觉的行为。这些受阻尿素可以被认为是原位释放反应性异氰酸酯的掩蔽试剂。

  DOI：

  10.1002/anie.200904435
• 作为产物：
  描述：

  N-叔丁基乙胺 、 异氰酸苯酯 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-叔丁基-1-乙基-3-苯基脲
  参考文献：
  名称：

  Stabilization of the hindered urea bond through de-tert-butylation

  摘要：

  一种简便的酸辅助的脱tert-丁基化反应，可以立即“关闭”受阻尿素键（HUBs）的动态性并稳定含有HUB的结构。

  DOI：

  10.1039/d1cc00715g

文献信息

• Dynamic Ureas with Fast and pH‐Independent Hydrolytic Kinetics
  作者：Kaimin Cai、Hanze Ying、Jianjun Cheng

  DOI：10.1002/chem.201801138

  日期：2018.5.23

  and synthesis of a new type of hydrolysable polymer that has identical hydrolysis kinetics from pH 3 to 11. The unprecedented pH independent hydrolytic kinetics of the aryl ureas were shown to be related to the dynamic bond dissociation controlled hydrolysis mechanism; the resulting hindered poly(aryl urea) can be degraded with a hydrolysis half‐life of 10 min in solution. More importantly, these fast

  低成本，高性能的可水解聚合物在生物医学应用和材料工业中非常重要。尽管许多应用要求材料具有对外部pH值不敏感的降解特性以在不同条件下实现一致的释放特性，但迄今为止开发的可水解化学技术具有pH依赖的水解动力学。这项工作报告了一种新型可水解聚合物的设计和合成，该新型可水解聚合物在pH 3至11范围内具有相同的水解动力学。芳基脲的前所未有的独立于pH值的水解动力学被证明与动态键解离控制的水解机理有关。所得到的受阻聚（芳基脲）在溶液中的水解半衰期为10分钟，可以被降解。更重要的是，这些快速可降解的受阻芳族聚脲可以容易地通过市售单体的加成聚合反应制备，并且在室温下可抵抗固体形式的水解达数月之久。在聚脲材料中，具有良好的固态稳定性和在各种pH值下快速水解的组合特性在聚脲材料中是空前的，并将对材料设计和应用（例如牺牲性涂料和生物材料）产生影响。
• Dynamic urea bonds with fast hydrolytic kinetics for polymers
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US10822448B2

  公开（公告）日：2020-11-03

  The present invention relates to polymers having dynamic urea bonds and more specifically to polymers having hindered urea bonds (HUBs) with fast hydrolytic kinetics. These urea bonds are aryl-substituted, i.e. aromatic-substituted hindered urea bonds, that demonstrate pH independent hydrolytic kinetics, such that they consistently and rapidly hydrolyze in water from pH 2 to 11. The urea bond dissociation for these materials is generally such that k−1>h−1, which is two orders of magnitudes faster than for aliphatic hindered ureas. The present invention also relates to hydrolytically reversible or degradable linear, branched or network polymers incorporating these HUBs and to precursors for incorporation of these HUBs into these polymers. The technology can be applied to and integrated into a variety of polymers, such as polyureas, polyurethanes, polyesters, polyamides, polycarbonates, polyamines, and polysaccharides to make linear, branched, and cross-linked polymers. Polymers incorporating these HUBs can be used in a wide variety of applications including for example, environmentally compatible packaging materials and biomedical applications, such as drug delivery systems and tissue engineering. In other embodiments, the HUBs can be used in self-healing polymers.

  本发明涉及具有动态脲键的聚合物，更具体地说，涉及具有快速水解动力学的受阻脲键 （HUB）的聚合物。这些脲键是芳基取代的，即芳香取代的受阻脲键，其水解动力学与 pH 值无关，因此它们在 pH 值为 2 到 11 的水中可持续快速水解。这些材料的脲键解离速度一般为 k-1>h-1，比脂肪族受阻脲快两个数量级。本发明还涉及含有这些 HUB 的水解可逆或可降解线性、支链或网络聚合物，以及将这些 HUB 纳入这些聚合物的前体。该技术可应用于各种聚合物，如聚脲、聚氨酯、聚酯、聚酰胺、聚碳酸酯、聚胺和多糖，并可与之结合，制成线性、支链和交联聚合物。含有这些 HUB 的聚合物可用于多种应用领域，例如环保型包装材料和生物医学应用，如药物输送系统和组织工程。在其他实施例中，HUBs 可用于自愈合聚合物。
• [EN] DYNAMIC UREA BONDS WITH FAST HYDROLYTIC KINETICS FOR POLYMERS<br/>[FR] LIAISONS URÉE DYNAMIQUES À CINÉTIQUE HYDROLYTIQUE RAPIDE POUR POLYMÈRES
  申请人：UNIV ILLINOIS

  公开号：WO2017155958A1

  公开（公告）日：2017-09-14

  The present invention relates to polymers having dynamic urea bonds and more specifically to polymers having hindered urea bonds (HUBs) with fast hydrolytic kinetics. These urea bonds are ary!-substituted, i.e. aromatic-substituted hindered urea bonds, that demonstrate pH independent hydrolytic kinetics, such that they consistently and rapidly hydroiyze in water from pH 2 to 11. The urea bond dissociation for these materials is generally such that k-1> h-1, which is two orders of magnitudes faster than for aliphatic hindered ureas. The present invention also relates to hydrolytically reversible or degradable linear, branched or network polymers incorporating these HUBs and to precursors for incorporation of these HUBs into these polymers. The technology can be applied to and integrated into a variety of polymers, such as polyureas, polyurethanes, polyesters, polyamides, polycarbonates, polyamines, and polysaccharides to make linear, branched, and cross-linked polymers. Polymers incorporating these HUBs can be used in a wide variety of applications including for example, environmentally compatible packaging materials and biomedical applications, such as drug delivery systems and tissue engineering. In other embodiments, the HUBs can be used in self-healing polymers.
• Hindered Ureas as Masked Isocyanates: Facile Carbamoylation of Nucleophiles under Neutral Conditions
  作者：Marc Hutchby、Chris E. Houlden、J. Gair Ford、Simon N. G. Tyler、Michel R. Gagné、Guy C. Lloyd-Jones、Kevin I. Booker-Milburn

  DOI：10.1002/anie.200904435

  日期：2009.11.2

  better: Sterically hindered dialkyl ureas undergo nucleophilic substitution at dramatically faster rates than their less hindered counterparts (see scheme). Steric decompression upon the formation of an intermediate isocyanate can explain this counterintuitive behavior. These hindered ureas can be considered as masked reagents that liberate reactive isocyanates in situ.

  越大越好：空间受阻的二烷基脲以比受阻较小的对应物快得多的速率进行亲核取代（参见方案）。中间体异氰酸酯形成时的空间减压可以解释这种违反直觉的行为。这些受阻尿素可以被认为是原位释放反应性异氰酸酯的掩蔽试剂。
• Stabilization of the hindered urea bond through de-<i>tert</i>-butylation
  作者：Yingfeng Yang、Hanze Ying、Yunchao Jia、Yingying Chen、Jianjun Cheng

  DOI：10.1039/d1cc00715g

  日期：——

  A facile acid-assisted de-tert-butylation reaction that can instantly “turn off” the dynamicity of hindered urea bonds (HUBs) and stabilize HUB-containing structures.

  一种简便的酸辅助的脱tert-丁基化反应，可以立即“关闭”受阻尿素键（HUBs）的动态性并稳定含有HUB的结构。