4-(9-fluorenylmethyloxycarbonyl)[N,N,N-tris(tert-butyloxycarbonyl)]phenylhydrazine | 726191-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(9-fluorenylmethyloxycarbonyl)[N,N,N-tris(tert-butyloxycarbonyl)]phenylhydrazine
• 英文别名: tri-tert-butyl 2-(4-fmoc-phenyl)hydrazine-1,1,2-tricarboxylate；9H-fluoren-9-ylmethyl 4-[[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-[(2-methylpropan-2-yl)oxycarbonyl]amino]benzoate
• CAS: 726191-64-6
• 化学式: C₃₆H₄₂N₂O₈
• 分子量: 630.738
• InChiKey: JSZFTBREHBRUPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 4-(9-fluorenylmethyloxycarbonyl)[N,N,N-tris(tert-butyloxycarbonyl)]phenylhydrazine 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine trifluoroacetic acid salt
  参考文献：
  名称：

  4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH):  A New Chromophoric Reagent for Quantitative Monitoring of Solid-Phase Aldehydes^1-3

  摘要：

  A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N-dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (epsilon(301nm) = 7800 M-1 cm(-1)) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

  DOI：

  10.1021/jo049830b
• 作为产物：
  描述：

  4-肼基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 4-(9-fluorenylmethyloxycarbonyl)[N,N,N-tris(tert-butyloxycarbonyl)]phenylhydrazine
  参考文献：
  名称：

  4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH):  A New Chromophoric Reagent for Quantitative Monitoring of Solid-Phase Aldehydes^1-3

  摘要：

  A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N-dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (epsilon(301nm) = 7800 M-1 cm(-1)) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

  DOI：

  10.1021/jo049830b

文献信息

• Polystyrene Sulfonyl Chloride: A Highly Orthogonal Linker Resin for the Synthesis of Nitrogen-Containing Heterocycles
  作者：Matthias Mentel、Axel M. Schmidt、Michael Gorray、Peter Eilbracht、Rolf Breinbauer

  DOI：10.1002/anie.200901643

  日期：2009.7.27

  One linker, broad application: A simple sulfonamide linker for primary and secondary amines was used for the construction of small libraries of privileged indole and quinolone structures on a solid phase. After the synthesis, the products can be liberated ion a traceless manner under electron transfer conditions or according to a “safety catch” principle.

  一个接头，广泛应用：用于伯胺和仲胺的简单磺酰胺接头用于在固相上构建具有特权吲哚和喹诺酮结构的小型文库。合成后，可以在电子转移条件下或根据“安全捕获”原理以无痕迹的方式释放产物。
• 4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH):  A New Chromophoric Reagent for Quantitative Monitoring of Solid-Phase Aldehydes^1-3
  作者：Simon K. Shannon、George Barany

  DOI：10.1021/jo049830b

  日期：2004.7.1

  A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N-dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (epsilon(301nm) = 7800 M-1 cm(-1)) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).