9H-fluoren-9-ylmethyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate | 391624-35-4

• 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 (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate
• CAS: 391624-35-4
• 化学式: C₂₀H₂₀N₄O₂
• 分子量: 348.404
• InChiKey: GGCGEGKSDYITKU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate 在 10percent Pd/C 氢气 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 [(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidin-2-yl]methylazanium;chloride
  参考文献：
  名称：

  Solid-Phase Synthesis of Oligourea Peptidomimetics Employing the Fmoc Protection Strategy

  摘要：

  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).

  DOI：

  10.1021/jo010656q
• 作为产物：
  描述：

  FMOC-脯氨醇 在 咪唑 、 sodium azide 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 9H-fluoren-9-ylmethyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Mild and Efficient Synthesis of Fmoc-Protected Amino Azides from Fmoc-Protected Amino Alcohols

  摘要：

  Fmoc保护的氨基叠氮化物 - 聚氨基脲和胍的单体关键中间体 - 可以通过碘化和随后用叠氮化钠取代的方法，从相应的氨基醇高效制备。该合成路线避免了在另一种方法中制备、储存和处理高度毒性的叠氮酸。

  DOI：

  10.1055/s-2005-923589

文献信息

• Sugar-Based Pyrrolidine as a Highly Enantioselective Organocatalyst for Asymmetric Michael Addition of Ketones to Nitrostyrenes
  作者：Lei Wang、Jie Liu、Tao Miao、Wei Zhou、Pinhua Li、Kai Ren、Xiuli Zhang

  DOI：10.1002/adsc.201000162

  日期：2010.10.4

  A modular sugar-based pyrrolidine (3) was prepared and was found to be a highly enantioselective organocatalyst for the asymmetric Michael addition of ketones to nitrostyrenes. In the presence of 10 mol% of 3, a pyrrolidine unit anchored to a natural D-glucose backbone through click chemistry, the Michael additions of ketones to nitrostyrenes proceeded smoothly to generate the corresponding adducts

  制备了模块化的基于糖的吡咯烷（3），发现其是用于酮向硝基苯乙烯的不对称迈克尔加成的高度对映选择性的有机催化剂。在10摩尔％的3（通过点击化学固定在天然D-葡萄糖主链上的吡咯烷单元）存在下，酮向硝基苯乙烯的迈克尔加成反应顺利进行，从而以高收率（最高98％）生成了相应的加合物在无溶剂的反应条件下，对映选择性（高达> 99％ee）和出色的非对映选择性（高达> 99：1 dr）。
• 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。
• <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).
• Solid-Phase and Solution-Phase Syntheses of Oligomeric Guanidines Bearing Peptide Side Chains
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1021/jo051226t

  日期：2005.10.1

  Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common a-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.
• Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1016/j.tetlet.2005.11.111

  日期：2006.1

  Peptidotriazoles, unnatural oligomers with alternating amide and triazole linkages, are synthesized efficiently on solid support. The key transformations involve multiple cycles of 1,2,3-triazolc formation, using soluble Cu(I) catalyst and conditions that do not generate precipitate on solid support nor require exclusion of oxygen. Our synthetic protocol will enable the preparation of other unnatural oligomers with multiple triazoles using solid phase methodologies. (c) 2005 Elsevier Ltd. All rights reserved.