cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester | 1382351-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
• 英文别名: cyano-hydroxyimino-acetic acid 2,3-dihydroxy-propyl ester；glycero-oxyma；2,3-Dihydroxypropyl 2-cyano-2-hydroxyiminoacetate；2,3-dihydroxypropyl 2-cyano-2-hydroxyiminoacetate
• CAS: 1382351-54-3
• 化学式: C₆H₈N₂O₅
• 分子量: 188.14
• InChiKey: UXUSHJIOEXNFNL-UHFFFAOYSA-N

物化性质

• 沸点：
  450.6±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2,2-dimethyl-1,3-dioxolan-4-yl)methyl cyanoacetate 在 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 cyano-hydroxyimino-acetic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
  参考文献：
  名称：

  A New Oxyma Derivative for Nonracemizable Amide-Forming Reactions in Water

  摘要：

  An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.

  DOI：

  10.1021/ol3013556

文献信息

• [EN] COMPOUNDS FOR AMIDE-FORMING REACTIONS<br/>[FR] COMPOSÉS POUR DES RÉACTIONS DE FORMATION D'AMIDE
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2013180815A1

  公开（公告）日：2013-12-05

  Provided herein is a compound of Formula I, that displays remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water, wherein said coupling reactions proceed without measurable racemization. A method of producing the compound of Formula I comprising reaction of a malononitrile precursor compound with sodium nitrite and glacial acetic acid, is also provided.

  本文提供的是一种具有显著物理化学性质的化合物，作为肽偶联添加剂用于水中的肽形成反应，其中所述的偶联反应在没有可测量的旋光异构化的情况下进行。还提供了一种制备公式I化合物的方法，包括将丙二腈前体化合物与亚硝酸钠和冰乙酸反应。
• A New Oxyma Derivative for Nonracemizable Amide-Forming Reactions in Water
  作者：Qinghui Wang、Yong Wang、Michio Kurosu

  DOI：10.1021/ol3013556

  日期：2012.7.6

  An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.