Dibenzyl naphthalene-2,3-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Dibenzyl naphthalene-2,3-dicarboxylate
• 英文别名: dibenzyl naphthalene-2,3-dicarboxylate
• 化学式: C₉H₆NO₂Pol
• 分子量: 396.4
• InChiKey: FZGZABQQUDDIIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dibenzyl naphthalene-2,3-dicarboxylate 在 甲胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 aminomethyl-terminated Tentagel resin
  参考文献：
  名称：

  Scale-Up of the Synthesis of a Pyrimidine Derivative Directly on Solid Support

  摘要：

  The solid-phase synthesis of 4-(2-amino-6-phenylpyrimidin-4-yl)benzamide, a compound obtained through combinatorial chemistry and parallel synthesis, can be scaled up directly on solid support in excellent yields and high purity. By applying highly loaded aminomethyl polystyrene as solid support, a good ratio between the product and the starting resin is achieved. For comparison, the synthesis was also performed in solution. The solid-phase synthesis approach has the advantage that the desired compound is easily and quickly accessible in sufficient quantities for early development demands.

  DOI：

  10.1021/op034032t
• 作为产物：
  描述：

  graphite 、 N-羟甲基邻苯二甲酰亚胺 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 Dibenzyl naphthalene-2,3-dicarboxylate
  参考文献：
  名称：

  制备氨基甲基聚苯乙烯树脂的改进方法及其在固相（肽）合成中的应用

  摘要：

  在氨基甲基聚苯乙烯树脂的制备中，使用2-氨基乙醇连续替代了肼，从而促进了纯化和副产物的去除。多肽ACP（65-74）和催产素的合成表明，以这种方式制备的氨基甲基聚苯乙烯树脂的使用等于或优于使用肼法制备的氨基甲基聚苯乙烯树脂。

  DOI：

  10.1016/j.tetlet.2011.09.010

文献信息

• Enantioselective Synthesis of N-Protected α-Amino Acid Hydrazides
  作者：Jean-Alain Fehrentz、Mathieu Bibian、Sarah El-Habnouni、Jean Martinez

  DOI：10.1055/s-0028-1088013

  日期：2009.4

  A new, mild, general, and efficient synthesis of N-protected α-amino acid hydrazides is described. This two-step preparation uses N-aminophthalimide as protected hydrazine to prepare N-protected α-amino acid hydrazide precursors, and subsequent de­phthaloylation with an aminomethyl polystyrene resin yields N-protected α-amino acid hydrazides. It has the advantages of avoiding the use of the toxic hydrazine reagent and being compatible with the most commonly used N-protecting groups. This strategy is particularly interesting in the case of N-(9-fluorenylmethoxycarbonyl)-protected amino acids. Within the limits of chiral HPLC detection, no epimerization is apparent.

  描述了一种新的、温和的、通用的且高效的N-保护α-氨基酸酰肼合成方法。该两步法利用N-氨基酞菁作为保护性酰肼制备N-保护α-氨基酸酰肼前体，随后通过氨基甲基聚苯乙烯树脂的去酞菁化反应得到N-保护α-氨基酸酰肼。其优点在于避免了使用有毒的酰肼试剂，并与最常用的N-保护基团相容。对于N-(9-芴基甲氧羰基)保护的氨基酸而言，该策略尤为有趣。在手性HPLC检测的限制范围内，未观察到外消旋化现象。
• Rapid Chemoselective Deprotection of Benzyl Esters by Nickel Boride
  作者：Jitender Khurana、Reema Arora

  DOI：10.1055/s-0028-1087982

  日期：2009.4

  Benzyl esters of a variety of acids can be chemoselectively cleaved on treatment with nickel boride in methanol at ambient temperature to give the parent carboxylic acids in high yields. Other protecting functionalities such as methyl, ethyl, tert-butyl, and trityl esters as well as benzyl ethers, tert-butyl ethers, and N-benzylamides are unaffected under these conditions.

  多种酸的苄酯在室温下使用镍硼化物处理甲醇溶液时，可以进行化学选择性裂解，以高产率得到母体羧酸。其他保护功能团，如甲酯、乙酯、叔丁酯、三苯甲酯、苄醚、叔丁醚以及N-苄基酰胺，在这些条件下均不受影响。
• An improved procedure for the preparation of aminomethyl polystyrene resin and its use in solid phase (peptide) synthesis
  作者：Paul W.R. Harris、Sung Hyun Yang、Margaret A. Brimble

  DOI：10.1016/j.tetlet.2011.09.010

  日期：2011.11

  2-Aminoethanol was used to successively replace hydrazine in the preparation of aminomethyl polystyrene resin thereby facilitating purification and by-product removal. The syntheses of the polypeptides ACP (65–74) and oxytocin demonstrated that the use of aminomethyl polystyrene resin prepared in this manner was equal to or better than that prepared using the hydrazine method.

  在氨基甲基聚苯乙烯树脂的制备中，使用2-氨基乙醇连续替代了肼，从而促进了纯化和副产物的去除。多肽ACP（65-74）和催产素的合成表明，以这种方式制备的氨基甲基聚苯乙烯树脂的使用等于或优于使用肼法制备的氨基甲基聚苯乙烯树脂。
• Scale-Up of the Synthesis of a Pyrimidine Derivative Directly on Solid Support
  作者：Mark Meisenbach、Thomas Allmendinger、Ching-Pong Mak

  DOI：10.1021/op034032t

  日期：2003.7.1

  The solid-phase synthesis of 4-(2-amino-6-phenylpyrimidin-4-yl)benzamide, a compound obtained through combinatorial chemistry and parallel synthesis, can be scaled up directly on solid support in excellent yields and high purity. By applying highly loaded aminomethyl polystyrene as solid support, a good ratio between the product and the starting resin is achieved. For comparison, the synthesis was also performed in solution. The solid-phase synthesis approach has the advantage that the desired compound is easily and quickly accessible in sufficient quantities for early development demands.