Ethyl 2-[[benzyl(phenylmethoxycarbonyl)amino]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate | 194664-33-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-[[benzyl(phenylmethoxycarbonyl)amino]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate
• CAS: 194664-33-0
• 化学式: C₂₄H₃₀N₂O₆
• 分子量: 442.512
• InChiKey: CQNVEJCWBUOVBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[[benzyl(phenylmethoxycarbonyl)amino]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [N'-Benzyl-N'-benzyloxycarbonyl-N-(2,2-dimethyl-propionyl)-hydrazino]-acetic acid ethyl ester
  参考文献：
  名称：

  Stepwise synthesis of tetrasubstituted hydrazines

  摘要：

  一种新的三保护肼试剂已被制备并应用于烷基化/酰基化反应，可用于高纯度和高产率的四取代衍生物的逐步合成。

  DOI：

  10.1039/a703008h
• 作为产物：
  描述：

  肼基甲酸苄酯 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 aluminum amalgam 、 二氧化碳 、 水 、 四丁基硫酸氢铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 、 苯 为溶剂， 生成 Ethyl 2-[[benzyl(phenylmethoxycarbonyl)amino]-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate
  参考文献：
  名称：

  Stepwise synthesis of tetrasubstituted hydrazines

  摘要：

  一种新的三保护肼试剂已被制备并应用于烷基化/酰基化反应，可用于高纯度和高产率的四取代衍生物的逐步合成。

  DOI：

  10.1039/a703008h

文献信息

• Experiments related to the synthesis and analysis of a hydrazine library †
  作者：Ulf Ragnarsson、Bengt Fransson、Leif Grehn

  DOI：10.1039/b000139m

  日期：——

  Substitutions under competition conditions are performed with a triprotected hydrazine reagent A as nucleophile and various halides as electrophiles and the product distribution determined by HPLC. Subsequently, after partial deprotection, stepwise substitution on the other nitrogen is studied similarly in order to define the scope of such reagents for the synthesis of libraries comprising multisubstituted hydrazines. In the course of this work a large number of partially protected hydrazine derivatives are prepared and characterized spectroscopically and chromatographically. The results indicate that n-alkyl and benzyl halides are of comparable reactivity under the conditions used, whereas others deviate too much in this respect as a result of which product mixtures severely distorted from equimolar ones are formed. In the course of this work, hydrazine libraries containing up to nine components are characterized quantitatively.

  在竞争条件下，使用三保护氢肼试剂A作为亲核试剂，采用各种卤化物作为电亲和体进行取代反应，并通过高效液相色谱（HPLC）确定产物分布。随后，在部分去保护后，研究其他氮上的逐步取代反应，以明确这种试剂在合成包含多取代氢肼的文库中的适用范围。在此过程中，制备和表征了大量部分保护的氢肼衍生物，采用光谱学和色谱学方法进行分析。结果表明，n-烷基和苄基卤化物在所用条件下的反应性相当，而其他卤化物由于反应性差异过大，导致形成的产物混合物严重偏离等摩尔比。在此工作中，最多包含九个组分的氢肼文库经过定量表征。
• Synthesis of Substituted Hydrazines from Triprotected Precursors.
  作者：Uno Mäeorg、Tönis Pehk、Ulf Ragnarsson

  DOI：10.3891/acta.chem.scand.53-1127

  日期：——

  Full details related to the preparation and application of two triprotected reagents, 1,2,2-Boc(3)-hydrazine (1) and 1,2-Boc(2)-2-Z-hydrazine (2), for stepwise synthesis of substituted hydrazines are presented. In the presence of base these compounds undergo substitution at N-1, often accompanied by partial loss of protecting groups at N-2. Optimized alkylation procedures, eliminating or greatly diminishing these side reactions, involving phase-transfer catalysis are reported. The initial products can be selectively deprotected at N-2 to provide a new alkylation site. Twice alkylated derivatives of 1 and 2 differ in their potential to undergo further selective cleavage, and only the latter are capable of such. A limited number of partly protected substituted hydrazine derivatives have been made using the novel procedures. Compounds 1 and 2 both exist as mixtures of two conformers which have been assigned, whereas in alkylated derivatives up to four such are present. For two dialkylated compounds all conformers have also been assigned and their relative distribution experimentally determined. The results are in good agreement with those from theoretical calculations.
• Synthesis, application and scope of a new protected hydrazine reagent
  作者：Uno Mäeorg、Ulf Ragnarsson

  DOI：10.1016/s0040-4039(97)10634-7

  日期：1998.2

  A novel triprotected hydrazine reagent, 1,2-Boc(2)-2-Z-hydrazine (3), has been made and investigated with respect to stepwise alkylation/acylation and intermediary deprotection in order to prepare multisubstituted hydrazine derivatives. Alkylation of 3 requires particularly mild basic conditions. Regiospecific cleavage of one Boc-group with acid in monoalkylated product 4 is difficult but on be accomplished with catalytic amounts of Mg(ClO4)(2) in MeCN at 50 degrees C in 15 min, furnishing 5 which can easily be alkylated to 6. This product has recently been converted to fully substituted derivatives 7. (C) 1998 Elsevier Science Ltd. All lights reserved.
• Stepwise synthesis of tetrasubstituted hydrazines
  作者：Leif Grehn、Hans Lönn、Ulf Ragnarsson

  DOI：10.1039/a703008h

  日期：——

  A new triprotected hydrazine reagent has been made and applied in alkylation/acylation reactions for stepwise synthesis of tetrasubstituted derivatives in high purity and yield.

  一种新的三保护肼试剂已被制备并应用于烷基化/酰基化反应，可用于高纯度和高产率的四取代衍生物的逐步合成。