2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile

• 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: 2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile
• 英文别名: tert-butyl (1-phenylethylideneamino) carbonate
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: ZJVOJNIXIYPQAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile 在 copper(l) iodide 、 sodium hydrogensulfite 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以82%的产率得到乙酰苯吖嗪
  参考文献：
  名称：

  Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines

  摘要：

  A facile, mild, and efficient copper-catalyzed homocoupling of ketoximes involving N-O bond cleavage in the presence of sodium bisulfite (NaHSO3) has been developed. This reaction shows good functional group tolerance and affords a broad scope of azines in high yields.

  DOI：

  10.1055/s-0031-1290779
• 作为产物：
  描述：

  苯乙酮肟 、 二碳酸二叔丁酯 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以98%的产率得到2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile
  参考文献：
  名称：

  Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines

  摘要：

  A facile, mild, and efficient copper-catalyzed homocoupling of ketoximes involving N-O bond cleavage in the presence of sodium bisulfite (NaHSO3) has been developed. This reaction shows good functional group tolerance and affords a broad scope of azines in high yields.

  DOI：

  10.1055/s-0031-1290779

文献信息

• Approaches to the synthesis of endothiopeptides: Synthesis of a thioamide-containing C-terminal bombesin nonapeptide
  作者：Jurjus Jurayj、Mark Cushman

  DOI：10.1016/s0040-4020(01)89436-9

  日期：——

  Several approaches have been investigated for the synthesis of a bombesin C-terminal nonapeptide analogue AsnGlnTrpAlaVAlGlyHisLeu-ψCSNHMet-NH2. A new activated dithioester 16 has been synthesized. Thioacylation of methionine methyl ester with 16 was always accompanied by racemization, resulting in the formation of diastereomeric mixtures of reaction products.

  几种方法已被研究用于铃蟾肽C-末端九肽类似物AsnGlnTrpAlaVAlGlyHisLeu-ψCSNHMet-NH的合成2。已经合成了新的活化的二硫酯16。甲硫氨酸甲酯与16的硫酰化总是伴随着消旋作用，导致反应产物的非对映异构体混合物的形成。
• Iron-Catalyzed Cyclization of Ketoxime Carboxylates and Tertiary Anilines for the Synthesis of Pyridines
  作者：Mi-Na Zhao、Zhi-Hui Ren、Le Yu、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/acs.orglett.6b00326

  日期：2016.3.4

  Fe-catalyzed N–O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.

  开发了新颖高效的铁催化的酮肟羧酸盐和N，N-二烷基苯胺的环化反应，以合成各种吡啶。在叔苯胺存在下，Fe催化酮肟羧酸酯的N–O键裂解，从而引发了反应。N，N-二烷基苯胺上的亚甲基碳在反应中用作一碳合成子的来源。该反应使用容易获得的起始原料，耐受各种官能团，并在温和条件下以高至高收率得到2,4-二取代和2,4,6-三取代的吡啶。
• 一种碳酸肟酯类化合物的制备方法及其应用
  申请人：河南农业大学

  公开号：CN117720433A

  公开（公告）日：2024-03-19

  本发明属于农药技术领域，特别是指一种碳酸肟酯类化合物的制备方法及其应用，用以解决肟酯合成工艺中合成成本高且对环境危害较大的技术问题。通过将芳香酮肟类化合物、偶氮化合物与金属盐溶于溶剂中，经90‑110℃反应1‑3h后得到碳酸肟酯类化合物。所制备的碳酸肟酯类化合物是一种有用的化工、医药中间体，作为有效的杀菌剂在生物活性方面也有着很重要的应用。本发明在温和、绿色的反应条件下实现了芳香酮肟类化合物的酯基化，为芳香酮肟类化合物的酯基化提供了一种便捷、高效的方法。同时，所制备的一系列碳酸肟酯类化合物测试了其对植物真菌的抑制活性，筛选出了新型、高效具有光谱杀菌作用的化合物，为开发新型绿色农药提供新颖构架的活性化合物。
• Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine <i>N</i>-Oxides from Oximes and Diazo Compounds
  作者：Zhuangzhi Shi、Dennis C. Koester、Mélissa Boultadakis-Arapinis、Frank Glorius

  DOI：10.1021/ja406338r

  日期：2013.8.21

  Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N-2 and H2O as the byproducts, and displays a broad substituent scope.
• Synthesis, In Vitro, and In Silico Evaluation of Organometallic Technetium and Rhenium Thymidine Complexes with Retained Substrate Activity toward Human Thymidine Kinase Type 1
  作者：Dominique Desbouis、Harriet Struthers、Vojtech Spiwok、Tatiana Küster、Roger Schibli

  DOI：10.1021/jm800530p

  日期：2008.11.13

  Human cytosolic thymidine kinase (hTK1) has proven to be a suitable target for noninvasive imaging of cancer cell proliferation using radiolabeled substrates such as [F-18]fluorothymidine ([F-18]FLT). However, a thymidine tracer useful for single photon emission tomography (SPECT) based off the inexpensive radionuclide technetium-99m would be of significant interest. In this work, a series of thymidine derivatives labeled with the organometallic [M(CO)(3)](+) core (M = Tc-99m, Re) were synthesized. Neutral, cationic, and anionic complexes were readily formed in aqueous media. and all were substrates of recombinant hTK1 when incubated with ATP. The neutral complexes were phosphorylated to a greater extent than the charged complexes. The extent of phosphorylation was further improved by increasing the spacer length separating thymidine and the organometallic core. A molecular dynamics Simulation Study performed with a modified hTK1 structure Supported the experimental findings. In vitro cell internalization experiments performed if) a human neuroblastoma cell line (SKNMC) showed low uptake of the charged complexes but significant uptake for the neutral, lipophilic complexes with a log P value > 1.