2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl isothiocyanate | 690665-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl isothiocyanate
• 英文别名: SCNPbf；Pbf-isothiocyanate；Pbf-NCS；2,2,4,6,7-Pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl isothiocyanate；2,2,4,6,7-pentamethyl-N-(sulfanylidenemethylidene)-3H-1-benzofuran-5-sulfonamide
• CAS: 690665-11-3
• 化学式: C₁₄H₁₇NO₃S₂
• 分子量: 311.426
• InChiKey: HWDZDROOBXFNHG-UHFFFAOYSA-N

物化性质

• 沸点：
  442.9±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl isothiocyanate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Solution- and Solid-Phase Syntheses of Guanidine-Bridged, Water-Soluble Linkers for Multivalent Ligand Design

  摘要：

  Efficient syntheses of guanidine-bridged poly(ethylene glycol) linkers of various lengths in fully protected form are reported for both solution- and solid-phase protocols. The application of such linkers in the construction of water-soluble and high-affinity multivalent ligands against cholera toxin is demonstrated. Synthetic intermediates for multivalent ligands as large as 20 kDa in molecular weight have been assembled using presynthesized linkers. The final ligands are highly water-soluble, thus enabling proper biophysical characterization.

  DOI：

  10.1021/ol049835v
• 作为产物：
  描述：

  Tetrabutylammonium Rhodanide 、 2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯 以 二氯甲烷 为溶剂， 以60%的产率得到2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl isothiocyanate
  参考文献：
  名称：

  Synthesis of acylguanidine zanamivir derivatives as neuraminidase inhibitors and the evaluation of their bio-activities

  摘要：

  我们合成了一系列酰基胍修饰的扎那米韦类似物，并评估了它们对禽流感病毒（H1N1 和 H3N2）NAs 的抑制活性。其中，具有疏水性萘取代基的扎那米韦衍生物 3j 对 1 组 NA 的抑制活性最佳，IC50 为 20 nM。

  DOI：

  10.1039/c3ob40624e

文献信息

• Preparation of <i>N</i>^G-Substituted <scp>l</scp>-Arginine Analogues Suitable for Solid Phase Peptide Synthesis
  作者：Nathaniel I. Martin、Rob M. J. Liskamp

  DOI：10.1021/jo801517f

  日期：2008.10.3

  A high-yielding and concise preparation of N(G)-substituted L-arginine analogues, suitably protected for use in solid phase peptide synthesis, is reported. The synthesis of each analogue employed an activated thiourea intermediate that was converted under mild conditions to the desired L-arginine analogue (10 examples, each in near quantitative yield). Subsequent allyl group removal provided each analogue

  报道了一种高产率且简洁的N（G）-取代的L-精氨酸类似物的制剂，其经过适当保护可用于固相肽合成。每种类似物的合成均采用活化的硫脲中间体，该中间体在温和条件下转化为所需的L-精氨酸类似物（10个实例，每个均接近定量收率）。随后的烯丙基去除提供了每种类似物，其形式非常适合用于固相肽合成。
• Iodine-Mediated Guanidine Formation through Arylsulfonyl-Activated Thioureas
  作者：Jizhen Li、Erkang Fan、Cuiying Qin

  DOI：10.1055/s-0029-1217825

  日期：2009.9

  Reaction of arylsulfonyl thioureas with amines to form guanidines can be efficiently promoted through the use of iodine, instead of conventional reagents such as the Mukaiyama reagent or EDC. The general scope and limitations of the reaction are probed.

  通过使用碘而不是 Mukaiyama 试剂或 EDC 等传统试剂，可以有效地促进芳基磺酰基硫脲与胺反应生成胍类化合物。本文探讨了该反应的一般范围和局限性。
• 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.
• Tethered thiazolidinone dimers as inhibitors of the bacterial type III secretion system
  作者：Toni Kline、Kathleen C. Barry、Stona R. Jackson、Heather B. Felise、Hai V. Nguyen、Samuel I. Miller

  DOI：10.1016/j.bmcl.2009.01.047

  日期：2009.3

  Disruption of protein-protein interactions by small molecules is achievable but presents significant hurdles for effective compound design. In earlier work we identified a series of thiazolidinone inhibitors of the bacterial type III secretion system (T3SS) and demonstrated that this scaffold had the potential to be expanded into molecules with broad-spectrum anti-Gram negative activity. We now report on one series of thiazolidinone analogs in which the heterocycle is presented as a dimer at the termini of a series of linkers. Many of these dimers inhibited the T3SS-dependent secretion of a virulence protein at concentrations lower than that of the original monomeric compound identified in our screen. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of acylguanidine zanamivir derivatives as neuraminidase inhibitors and the evaluation of their bio-activities
  作者：Chien-Hung Lin、Tsung-Che Chang、Anindya Das、Ming-Yu Fang、Hui-Chen Hung、Kai-Cheng Hsu、Jinn-Moon Yang、Mark von Itzstein、Kwok Kong T. Mong、Tsu-An Hsu、Chun-Cheng Lin

  DOI：10.1039/c3ob40624e

  日期：——

  A series of acylguanidine-modified zanamivir analogs were synthesized and their inhibitory activities against the NAs of avian influenza viruses (H1N1 and H3N2) were evaluated. In particular, zanamivir derivative 3j, with a hydrophobic naphthalene substituent, exhibits the best inhibitory activity against group-1 NA with an IC50 of 20 nM.

  我们合成了一系列酰基胍修饰的扎那米韦类似物，并评估了它们对禽流感病毒（H1N1 和 H3N2）NAs 的抑制活性。其中，具有疏水性萘取代基的扎那米韦衍生物 3j 对 1 组 NA 的抑制活性最佳，IC50 为 20 nM。