(propan-2-ylideneamino) but-2-enoate | 133145-93-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (propan-2-ylideneamino) but-2-enoate
• CAS: 133145-93-4
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: MSPVNOXAROJSJR-UHFFFAOYSA-N

物化性质

• 沸点：
  181.9±23.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (propan-2-ylideneamino) but-2-enoate 、 尿嘧啶核苷 以 四氢呋喃 为溶剂， 反应 20.0h， 以85%的产率得到(E)-But-2-enoic acid (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction

  摘要：

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.

  DOI：

  10.1021/jo00055a018
• 作为产物：
  描述：

  vinyl crotonate 、 丙酮肟 以 异丙醚 为溶剂， 反应 12.0h， 以90%的产率得到(propan-2-ylideneamino) but-2-enoate
  参考文献：
  名称：

  Acylation and Alkoxycarbonylation of Oximes Through an Enzymatic Oximolysis Reaction

  摘要：

  酮或苯甲醛O-酰基肟和O-(叔丁氧羰基)肟可以通过分别使用酯酶作为生物催化剂，将肟与乙烯酯和二叔丁基二碳酸酯反应来制备。

  DOI：

  10.1055/s-1993-25798

文献信息

• Oxime Esters as Acylating Agents in the Aminolysis Reaction. A Simple and Chemoselective Method for the Preparation of Amides from Amino Alcohols
  作者：Susana Fernández、Emma Menéndez、Vicente Gotor

  DOI：10.1055/s-1991-26553

  日期：——

  Oxime esters, such as acetone O-alkanoyl-, O-alkenoyl- or O-benzyloxycarbonyloximes, react with amines under extremely mild conditions to give the corresponding amides in very good yield. When amino alcohols are used a total chemoselectivity is observed.

  烷基肟酯，如丙酮O-烷酰基、O-烯酰基或O-苄氧羰基肟，在极其温和的条件下与胺反应，以很高的产率生成相应的酰胺。当使用氨基醇时，观察到完全的化学选择性。
• A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction
  作者：Francisco Moris、Vicente Gotor

  DOI：10.1021/jo00055a018

  日期：1993.1

  Lipase-mediated acylation of nucleosides with oxime esters in organic solvents has been achieved. Candida antarctica lipases (SP435 and SP435A) showed high regioselectivity toward the primary hydroxyl group of both deoxy- and ribonucleosides, whereas other lipases exhibited poor results for this goal. 2'-Deoxynucleosides, such as thymidine and 2'-deoxyadenosine, were acylated with oxime esters carrying saturated, unsaturated, aromatic, and functionalized chains, giving 5'-O-acylated compounds together with small quantities of the 3'-O-acylated regioisomer. Uridine, adenosine, and inosine, as representative ribonucleosides, were acylated exclusively at the 5'-OH by using the same methodology. Nucleosides bearing a cytosine ring were found to be unreactive with oxime esters under the same conditions. 2'-Deoxycytidine was acylated with acid anhydrides and C. antarctica lipase to give N,5'-O-diacylated compounds, whereas cytidine gave mixtures, reason for which it had to be previously chemically N-acylated and then subjected to the oxime esters and lipase, giving the same results as ribonucleosides.
• Acylation and Alkoxycarbonylation of Oximes Through an Enzymatic Oximolysis Reaction
  作者：Emma Menéndez、Vicente Gotor

  DOI：10.1055/s-1993-25798

  日期：——

  Ketone or benzaldehyde O-acyloximes and O-(tert-butoxycarbonyl)oximes can be prepared by reaction of oximes with vinyl esters and di-tert-butyl dicarbonate, respectively, using lipases as biocatalysts.

  酮或苯甲醛O-酰基肟和O-(叔丁氧羰基)肟可以通过分别使用酯酶作为生物催化剂，将肟与乙烯酯和二叔丁基二碳酸酯反应来制备。