2,2,2-trichloroethyl N-(phenylmethoxycarbonylamino)carbamate | 202980-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2,2-trichloroethyl N-(phenylmethoxycarbonylamino)carbamate
• CAS: 202980-89-0
• 化学式: C₁₁H₁₁Cl₃N₂O₄
• 分子量: 341.578
• InChiKey: BDHUXCCXCZLOBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl N-(phenylmethoxycarbonylamino)carbamate 在 三甲基氯硅烷 、 mischmetal (50 percent Ce, 25 percent La, 16 percent Nd, 6 percent Pr) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以99%的产率得到肼基甲酸苄酯
  参考文献：
  名称：

  Vellemaee, Eerold; Lebedev, Oleg; Sillard, Rannar, Journal of Chemical Research, 2006, # 11, p. 685 - 687

  摘要：

  DOI：
• 作为产物：
  描述：

  肼基甲酸苄酯 、 氯甲酸-2,2,2-三氯乙酯 以90%的产率得到2,2,2-trichloroethyl N-(phenylmethoxycarbonylamino)carbamate
  参考文献：
  名称：

  Synthesis, application and scope of a new protected hydrazine reagent

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10634-7

文献信息

• 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.
• Juermann, Gea; Tsubrik, Olga; Tammeveski, Kaido, Journal of Chemical Research, 2005, # 10, p. 661 - 662
  作者：Juermann, Gea、Tsubrik, Olga、Tammeveski, Kaido、Maeeorg, Uno

  DOI：——

  日期：——
• Vellemaee, Eerold; Lebedev, Oleg; Sillard, Rannar, Journal of Chemical Research, 2006, # 11, p. 685 - 687
  作者：Vellemaee, Eerold、Lebedev, Oleg、Sillard, Rannar、Maeeorg, Uno

  DOI：——

  日期：——
• 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.