N-(tert-butoxycarbonyl)-dehydroalanine p-nitrobenzyl ester | 88950-54-3

• 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: N-(tert-butoxycarbonyl)-dehydroalanine p-nitrobenzyl ester
• 英文别名: 4-nitrobenzyl 2-[(tert-butoxycarbonyl)amino]acrylate；N-Boc-dehydroalanine p-nitrobenzyl ester；4-Nitrobenzyl 2-(tert-butoxycarbonylamino)acrylate；(4-nitrophenyl)methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]prop-2-enoate
• CAS: 88950-54-3
• 化学式: C₁₅H₁₈N₂O₆
• 分子量: 322.318
• InChiKey: TYXZKFKUZCKSRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-dehydroalanine p-nitrobenzyl ester 在 甲醇 、 sodium hydroxide 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 Boc-1-氨基环丙基甲酸
  参考文献：
  名称：

  A new synthesis of racemic coronamic acid and other cyclopropyl amino acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)94289-8
• 作为产物：
  描述：

  Boc-Ser.OpNB 在 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 氯仿 为溶剂， 以80%的产率得到N-(tert-butoxycarbonyl)-dehydroalanine p-nitrobenzyl ester
  参考文献：
  名称：

  A new synthesis of racemic coronamic acid and other cyclopropyl amino acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)94289-8

文献信息

• Efficient synthesis of protected cyclopropyl β-aspartylphosphates
  作者：Luke A. Adams、Jonathan P. H. Charmant、Russell J. Cox、Magnus Walter、William G. Whittingham

  DOI：10.1039/b311322a

  日期：——

  The in situ reaction of protected dehydroamino acids with derivatives of vinyldiazomethane leads to good to excellent yields of vinyl cyclopropanes via 3 + 2 dipolar cycloaddition followed by N(2) extrusion. Chromatographic separation of the cyclopropane diastereomeric products, followed by characterisation by (1)H NMR and X-ray crystallography allowed the cis and trans diastereomers to be easily identified

  受保护的脱氢氨基酸与乙烯基重氮甲烷衍生物的原位反应通过3 + 2偶极环加成，然后进行N（2）挤出，导致乙烯基环丙烷的收率良好。色谱分离环丙烷非对映异构体产物，然后通过（1）NMR和X射线晶体学进行表征，可以轻松鉴定出顺式和反式非对映体。乙烯基部分的氧化裂解随后可从市售材料中分三步直接得到受保护的环丙烷天冬氨酸衍生物。这些化合物被转化为β-天冬氨酰磷酸的保护的亚甲基膦酸酯，二氟亚甲基膦酸酯和氨基磷酸酯类似物。
• Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ
  作者：Luke A. Adams、Varinder K. Aggarwal、Roger V. Bonnert、Bettina Bressel、Russell J. Cox、Jon Shepherd、Javier de Vicente、Magnus Walter、William G. Whittingham、Caroline L. Winn

  DOI：10.1021/jo035060c

  日期：2003.11.1

  E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (+/-)-(Z)-2,3-methanophenylalanine [(+/-)-(Z)-1], the anti-Parkinson (+/-)-(E)-2,3-methano-m-tyrosine [(+/-)-(E)-2], and the natural product (+/-)-coronamic acid [(+/-)-3].

  描述了一种简单且高产率的制备环丙烷氨基酸的方法。该新方法涉及使用从相应的甲苯磺酰salts盐就地产生的芳基和不饱和重氮化合物对易得的脱氢氨基酸进行一锅环丙烷化。发现热的1，3-偶极环加成反应，接着进行氮挤出，得到具有良好E选择性的环丙烷氨基酸衍生物，而在中四苯基卟啉氯化铁存在下的反应主要产生了相应的Z异构体。在合成（+/-）-（Z）-2,3-methanophenylphenylineine [（+/-）-（Z）-1]，抗帕金森氏菌（+/-）中证明了该方法的合成效用-（E）-2，3-甲基-间-酪氨酸[（+/-）-（E）-2]和天然产物（+/-）-冠状酸[（+/-）-3]。
• Synthesis of cyclopropane amino acids
  申请人：The University of Georgia Research Foundation, Inc.

  公开号：US04629784A1

  公开（公告）日：1986-12-16

  Cyclopropane ("Cyclopropyl") amino acids and peptides containing at least one cyclopropyl amino acid are disclosed. The processes for synthesizing cyclopropyl amino acids and peptides containing at least one cyclopropyl amino acid are also disclosed. Cyclopropyl amino acids are useful as enzyme inhibitors and as substitutes for natural amino acids in peptide hormones such as regulators of bodily functions to enhance bioactivity, to stabilize the peptide into which it is incorporated to cleavage by enzymes and to convert such peptides into enzyme inhibitors.

  本发明揭示了含有至少一种环丙基氨基酸的环丙烷（“环丙基”）氨基酸和肽。还揭示了合成含有至少一种环丙基氨基酸的环丙烷氨基酸和肽的方法。环丙基氨基酸可用作酶抑制剂，并用作肽类激素中天然氨基酸的替代品，以增强生物活性，稳定其所包含的肽的酶解，并将这些肽转化为酶抑制剂。
• The synthesis of cyclopropane amino acids and peptides
  申请人：THE UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.

  公开号：EP0135429A1

  公开（公告）日：1985-03-27

  Cyclopropane ("cyclopropyl") amino acids and peptides containing at least one cyclopropyl amino acid are disclosed. The processes for synthesizing cyclopropyl amino acids and peptides containing at least one cyclopropyl amino acid are also disclosed. Cyclopropyl amino acids are useful as enzyme inhibitors and as substitutes for natural amino acids in peptide hormones such as regulators of bodily functions to enhance bioactivity, to stabilize the peptide into which it is incorporated to cleavage by enzymes and to convert such peptides into enzyme inhibitors. Specific dipeptides ∇Asp-Phe·OCH3 or Asp-V-Phe-OCH3 or ∇Asp-∇-Phe·OCH3 are described as a stabilized peptide sweetener for foods and beverages. Methods for synethesis of the cyclopropyl-amino acids, the acids themselves, peptides where the acids have been inserted and food and drug products employing those peptides are illustrated.

  本发明公开了环丙烷（"环丙基"）氨基酸和含有至少一种环丙基氨基酸的肽。还公开了合成环丙基氨基酸和含有至少一种环丙基氨基酸的肽的工艺。环丙基氨基酸可用作酶抑制剂和肽类激素（如身体功能调节剂）中天然氨基酸的替代品，以增强生物活性，稳定肽，使其不被酶裂解，并将这种肽转化为酶抑制剂。 ∇Asp-Phe-OCH3或Asp-V-Phe-OCH3或∇Asp-∇-Phe-OCH3作为一种稳定的肽甜味剂用于食品和饮料。 图中说明了环丙基氨基酸的合成方法、酸本身、插入酸的肽以及使用这些肽的食品和药物产品。
• Synthesis of (.+-.)-2,3-methanovaline and (.+-.)-2,3-methanoleucine
  作者：V. P. Srivastava、Malcolm Roberts、Timothy Holmes、Charles H. Stammer

  DOI：10.1021/jo00286a015

  日期：1989.12