tert-butyl (4-isocyanobenzyl)carbamate | 823806-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (4-isocyanobenzyl)carbamate
• 英文别名: 1-(4-isocyanophenyl)-N-Boc-methanamine；4-(N-Boc-aminomethyl)phenylisonitrile；tert-Butyl [(4-isocyanophenyl)methyl]carbamate；tert-butyl N-[(4-isocyanophenyl)methyl]carbamate
• CAS: 823806-52-6
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: YPYIUTHYXYMDSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-isocyanobenzyl)carbamate 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Pt(IV)Re(I)偶联物的光化学和体外抗癌活性

  摘要：

  通过实验和计算方法研究了两种 Pt( IV )Re( I ) 共轭物的光物理和光化学性质。两种偶联物都对卵巢癌细胞表现出适度的光细胞毒性。X 射线荧光显微镜显示 Pt 和 Re 在细胞中共定位，无论它们是否受到辐射。这项工作证明了光活化多金属试剂在抗癌方面的潜力。

  DOI：

  10.1039/d1cc04669a
• 作为产物：
  描述：

  4-(N-BOC-氨甲基)苯胺 在 三乙胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (4-isocyanobenzyl)carbamate
  参考文献：
  名称：

  Discovery and SAR of Novel and Selective Inhibitors of Urokinase Plasminogen Activator (uPA) with an Imidazo[1,2-a]pyridine Scaffold

  摘要：

  Urokinase plasminogen activator (uPA) is a biomarker and therapeutic target for several cancer types. Its inhibition is regarded as a promising, noncytotoxic approach in cancer therapy by blocking growth and/or metastasis of solid tumors. Earlier, we reported the modified substrate activity screening (MSAS) approach and applied it for the identification of fragments with affinity for uPA's Si pocket. Here, these fragments are transformed into a novel class of uPA inhibitors with an imidazo[1,2-a]pyridine scaffold. The SAR for uPA inhibition around this scaffold is explored, and the best compounds in the series have nanomolar uPA affinity and selectivity with respect to the related trypsin-like serine proteases (thrombin, tPA, FXa, plasmin, plasma kallikrein, trypsin, FVIIa). Finally, the approach followed for translating fragments into small molecules with a decorated scaffold architecture is conceptually straightforward and can be expected to be broadly applicable in fragment-based drug design.

  DOI：

  10.1021/acs.jmedchem.5b01171

文献信息

• Visible Light‐promoted C(sp3)‐H α‐Carbamoylation of Cyclic Ethers with Isocyanides
  作者：Camilla Russo、Carmine Volpe、Federica Santoro、Diego Brancaccio、Anna Di Porzio、Alfonso Carotenuto、Antonio Randazzo、Laurence Grimaud、Maxime R. Vitale、Stefano Protti、Mariateresa Giustiniano

  DOI：10.1002/chem.202401997

  日期：2024.8.27

  C(sp3)-H carbamoylation of cyclic ethers has been achieved via a domino sequence of Hydrogen Atom Transfer/Radical Polar Crossover pathways, finally enabling the nucleophilic addition of isocyanides to oxocarbenium ions. The current method features mild reaction conditions to generate oxocarbenium ions from non-activated ethers, along with good substrate scope and functional group compatibility.

  环醚的C( sp 3 )-H氨基甲酰化通过氢原子转移/自由基极性交叉途径的多米诺序列实现，最终实现异氰化物与氧碳鎓离子的亲核加成。目前的方法具有从非活化醚生成氧碳鎓离子的温和反应条件，以及良好的底物范围和官能团兼容性。
• Glyoxylic Acid and MP-Glyoxylate:  Efficient Formaldehyde Equivalents in the 3-CC of 2-Aminoazines, Aldehydes, and Isonitriles
  作者：Michael A. Lyon、Timothy S. Kercher

  DOI：10.1021/ol0478234

  日期：2004.12.1

  Glyoxylic acid, either in solution or immobilized on MP-carbonate (MP-glyoxylate), participates in an uncatalyzed 3-CC with 2-aminoazines and isonitriles to afford novel 2-unsubstituted-3-amino-imidazoheterocycles. MP-glyoxylate serves as a particularly efficient and experimentally convenient formaldehyde equivalent and readily liberates products through decarboxylation/self-release from the resin. These examples furthermore constitute the first application in which MP-CO3 serves as a solid support for transformations involving carboxylic acids.