N-diazoacetyl-D,L-phenylalanine methyl ester | 1438843-14-1

• 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: N-diazoacetyl-D,L-phenylalanine methyl ester
• 英文别名: methyl N-diazoacetyl-D,L-phenylalaninate
• CAS: 1438843-14-1
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: NRMULSJMFPZIST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.8
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-diazoacetyl-D,L-phenylalanine methyl ester 在 重水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以75%的产率得到methyl 2-(α-D-diazoacetamido)-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of Structure and Function Diverse α-D-Diazoacetates, α-D-Diazoacetamides, α-D-Diazoketones, and the Antibiotic α-D-Azaserine

  摘要：

  Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile-deuterium oxide mixture acts as a 'privileged' reaction system, which at ambient temperature affords, via a one-pot-one-cycle procedure, alpha-D-diazoacetates, alpha-D-diazoacetamides, or alpha-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-alpha-D-azaserine with >= 95% D-incorporation is reported.

  DOI：

  10.1055/s-0032-1318136
• 作为产物：
  描述：

  D-苯丙氨酸甲酯盐酸盐 在 sodium azide 、 silica gel 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 N-diazoacetyl-D,L-phenylalanine methyl ester
  参考文献：
  名称：

  Amphos 介导的烷基叠氮化物向重氮化合物的转化和一锅叠氮化物位点选择性瞬时保护、点击共轭和去保护转化

  摘要：

  概述了烷基叠氮化物向重氮化合物的一锅转化。 α-叠氮羰基化合物与Amphos反应后，在湿溶剂中用硅胶处理所得磷酰肼，得到α-重氮羰基产物。通过Amphos的叠氮基保护特性，叠氮基保护、点击官能化和重氮基脱保护的分子间和分子内叠氮位点选择性反应已被一锅展示。

  DOI：

  10.1021/acs.orglett.4c00566

文献信息

• Synthesis of Structure and Function Diverse α-D-Diazoacetates, α-D-Diazoacetamides, α-D-Diazoketones, and the Antibiotic α-D-Azaserine
  作者：Sean Bew、Polly-Anna Ashford、Dominika Bachera

  DOI：10.1055/s-0032-1318136

  日期：——

  Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile-deuterium oxide mixture acts as a 'privileged' reaction system, which at ambient temperature affords, via a one-pot-one-cycle procedure, alpha-D-diazoacetates, alpha-D-diazoacetamides, or alpha-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-alpha-D-azaserine with >= 95% D-incorporation is reported.
• Amphos-Mediated Conversion of Alkyl Azides to Diazo Compounds and One-Pot Azide-Site Selective Transient Protection, Click Conjugation, and Deprotective Transformation
  作者：Hiroki Tanimoto、Ryo Adachi、Kodai Tanisawa、Takenori Tomohiro

  DOI：10.1021/acs.orglett.4c00566

  日期：2024.3.29

  A one-pot conversion of alkyl azides to diazo compounds is outlined. After the reaction of α-azidocarbonyl compounds with Amphos, treatment of the resulting phosphazides with silica gel in a wet solvent afforded α-diazo carbonyl products. Through the azido group protection property of Amphos, inter- and intramolecular azide-site selective reactions of azido group protection, click functionalization

  概述了烷基叠氮化物向重氮化合物的一锅转化。 α-叠氮羰基化合物与Amphos反应后，在湿溶剂中用硅胶处理所得磷酰肼，得到α-重氮羰基产物。通过Amphos的叠氮基保护特性，叠氮基保护、点击官能化和重氮基脱保护的分子间和分子内叠氮位点选择性反应已被一锅展示。