9H-fluoren-9-ylmethyl N-[(2S)-1-azidopropan-2-yl]carbamate | 391624-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-fluoren-9-ylmethyl N-[(2S)-1-azidopropan-2-yl]carbamate
• CAS: 391624-27-4
• 化学式: C₁₈H₁₈N₄O₂
• 分子量: 322.367
• InChiKey: YDLDBWJTCMBGJD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-azidopropan-2-yl]carbamate 在 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-methyl 2-((E)-3-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)propyl)-2-(4-chlorophenyl)guanidino-1-yl)-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of N-urethane protected amino alkyl (S-methyl)-isothiouronium compounds and carbodiimide tethered peptidomimetics: an application for guanidino and substituted guanidino peptidomimetics synthesis

  摘要：

  已阐明了合成N,N′-二取代和N,N′,N′′-三取代的胍基连接肽模仿分子，这些分子在肽骨架中进行了适当的装饰。采用Nα-保护的氨基酸衍生的S-甲基异硫脲盐衍生物作为合成胍基肽模仿物的关键中间体。还概述了一类新型的碳二亚胺连接的二肽模仿物的合成，其中采用氨基烷基叠氮化物与异硫氰酸酯之间的斯陶丁格-阿扎-维蒂格反应。因此获得的碳二亚胺已被证明是构建胍基肽模仿物的起始材料，以及一系列具有N-羟基、氰基和氨基作为胍基单元中第三取代基的三取代胍基模仿物。

  DOI：

  10.1039/c4ra07252a
• 作为产物：
  描述：

  (S)-2-(N-fluorenylmethoxycarbonylamino)-iodopropane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 9H-fluoren-9-ylmethyl N-[(2S)-1-azidopropan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis of Hybrid Peptidomimetics and Neoglycoconjugates Employing Click Protocol: Dual Utility of Poc-Group for Inserting Carbamate-Triazole Units into Peptide Backbone

  摘要：

  描述了新型肽类似物和具有1,2,3-三唑和氨基甲酸酯基团的糖基氨基酸的合成。经Poc保护的氨基酸酯/1-氨基糖在点击反应条件下与所需的叠氮化合物进行Cu(I)催化的[2+3]环加成反应，以获得新型的肽和碳水化合物类似物。该反应快速、高效，所有产物均以良好的产率和优异的纯度分离得到。

  DOI：

  10.1007/s10989-010-9228-6

文献信息

• Late‐Stage Dehydroxyazidation of Alcohols Promoted by Trifunctional Hypervalent Azido‐Iodine(III) Reagents
  作者：Xiao‐Guang Yang、Feng‐Huan Du、Jun‐Jie Li、Chi Zhang

  DOI：10.1002/chem.202200272

  日期：2022.5.11

  We developed a mild, metal-free practical method for late-stage dehydroxyazidation of structurally complex alcohols promoted by trifunctional hypervalent azido-iodine(III) reagents ABZ. The reactions proceeded via an SN2 pathway and showed excellent chemoselectivity and stereospecificity and gave the corresponding azides in high yields. The reaction mechanism was investigated by means of experiments

  我们开发了一种温和、无金属的实用方法，用于由三官能高价叠氮碘 (III) 试剂 ABZ 促进的结构复杂醇的后期脱羟基叠氮化。该反应通过S N 2 途径进行，表现出优异的化学选择性和立体特异性，并以高收率得到相应的叠氮化物。通过实验和DFT计算研究了反应机理。
• Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates
  作者：L. Roopesh Kumar、Veladi Panduranga、T. M. Vishwanatha、Shekharappa Shekharappa、Vommina. V. Sureshbabu

  DOI：10.1039/c8ob00239h

  日期：——

  An unprecedented approach for the assembly of thioureido peptidomimetics is developed employing alkyl azides and dithiocarbamates. Dithiocarbamates react with alkyl azides with the liberation of N2 and elemental sulfur thereby leading to thiourea in a traceless manner. Thioureido peptidomimetics are thus furnished in good yields with no epimerization. This process is mild, free from the use of a base

  利用烷基叠氮化物和二硫代氨基甲酸酯开发了一种用于组装硫脲基拟肽的前所未有的方法。二硫代氨基甲酸酯与烷基叠氮化物反应，释放出N 2和元素硫，从而无痕地生成硫脲。硫脲基肽模拟物因此以高产率提供而没有差向异构化。这个过程是温和的，没有使用基础的，可扩展的和逐步的经济性。该方法的实用性已经通过N，N′-正交保护的硫脲基肽模拟物的合成得到强调。
• Solid-Phase Synthesis of Oligourea Peptidomimetics Employing the Fmoc Protection Strategy
  作者：Astrid Boeijen、Jeroen van Ameijde、Rob M. J. Liskamp

  DOI：10.1021/jo010656q

  日期：2001.12.1

  A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• WO2023/39068
  申请人：——

  公开号：——

  公开（公告）日：——