Fmoc-Phg-ψ[CH2I] | 1172596-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Phg-ψ[CH2I]
• CAS: 1172596-36-9
• 化学式: C₂₃H₂₀INO₂
• 分子量: 469.322
• InChiKey: KVQNFEFSDAALHB-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Phg-ψ[CH2I] 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Fmoc-Phg-ψ[CH2N3]
  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
• 作为产物：
  描述：

  Fmoc-l-alpha-苯丙氨醇 在 咪唑 、 碘 、 三苯基膦 作用下， 生成 Fmoc-Phg-ψ[CH2I]
  参考文献：
  名称：

  一种合成新型二硫代氨基甲酸酯连接的拟肽的简单方法

  摘要：

  描述了合成一系列新的二硫代氨基甲酸酯连接的拟肽的有效方案。由氨基酸酯与二硫化碳在三乙胺存在下反应形成的原位生成的二硫代氨基甲酸中间体用N保护的氨基烷基碘处理，以良好至中等的收率得到标题化合物3a – g。还描述了含有两个二硫代氨基甲酸酯键的N -Fmoc保护的三肽模拟物4a – e的合成。该协议被进一步扩展为合成N，N'-正交保护的二硫代氨基甲酸酯连接的二肽模拟物7a – c也一样 温和的反应条件和无毒试剂是本方法的优点。

  DOI：

  10.1016/j.tetlet.2009.09.172

文献信息

• Synthesis of N-Fmoc-Protected Amino Alkyl Thiocyanates/Selenocyanates and Their Application in the Preparation of 5-Substituted S/Se-Linked Tetrazoles
  作者：Vommina Sureshbabu、Basavalingappa Vasantha、Hosahalli Hemantha

  DOI：10.1055/s-0030-1259972

  日期：2011.5

  A novel class of N-Fmoc-protected amino alkyl thiocyanates/selenocyanates has been prepared by thiocyanation/selenocyanation of the corresponding alkyl iodides. These thiocyanates/selenocyanates undergo a facile [2+3]-cycloaddition reaction with sodium azide to afford novel N-Fmoc amino alkyl S/Se-linked tetrazoles. amino acid derivatives - thiocyanates - selenocyanates - [2+3] cycloaddition - S/Se-linked

  通过相应烷基碘的硫氰化/硒氰化制备了新型的N -Fmoc保护的氨基烷基硫氰酸酯/硒氰酸酯。这些硫氰酸盐/硒代氰酸盐与叠氮化钠进行简单的[2 + 3]-环加成反应，得到新颖的N- Fmoc氨基烷基S / Se-连接的四唑。 氨基酸衍生物-硫氰酸酯-硒氰酸酯-[2 + 3]环加成-S / Se相连的四唑
• Synthesis of an amino phosphinodiselenoic acid ester and β-amino diselenides employing P₂Se₅
  作者：L. Roopesh Kumar、N. R. Sagar、K. Divya、C. Madhu、Vommina V Sureshbabu

  DOI：10.1039/d0nj00012d

  日期：——

  The synthesis of a new class of amino phosphinodiselenoic acid ester and β-amino diselenides is conducted by employing a reaction between Nβ-protected aminoalkyl iodide and phosphorus pentaselenide (P2Se5) has been described. In the presence of protic solvents, amino phosphinodiselenoic acid esters were found to be the major products, whereas β-amino diselenides were formed exclusively when the reaction

  一类新的氨基phosphinodiselenoic酸酯和β氨基diselenides的合成通过采用之间的反应进行Ñ β -保护的氨基烷基碘和磷pentaselenide（P 2硒5）进行了说明。在质子溶剂存在下，发现氨基膦基二硒酸酯是主要产物，而β-氨基二硒化物仅在极性非质子溶剂中进行反应时形成。
• <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).
• A facile one-pot synthesis of Nα-Z/Boc-protected S-linked 1,3,4-oxadiazole tethered peptidomimetics
  作者：Vommina V. Sureshbabu、B. Vasantha、G. Nagendra

  DOI：10.1016/j.tetlet.2011.12.093

  日期：2012.3

  A new class of S-linked 1,3,4-oxadiazole-tethered N-alpha-protected peptidomimetics is designed and synthesized by a reaction of N-alpha-Z/Boc-protected 1,3,4-oxadiazole-2-thiol with alpha-bromo ester derived from amino acid. The protocol has also been employed for the synthesis of glycosylated amino acids and N,N'-orthogonally protected dipeptidomimetics bearing S-linked 1,3,4-oxadiazole mimetics as well. The intermediate 5-alkyl amino-1,3,4-oxadiazole-2-thiols have been isolated as stable compounds. Further, the chain extension at both N- and C-termini of N-protected S-linked 1,3,4-oxadiazole tethered dipeptidomimetics was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.