O-octanoyl acetoxime | 116709-88-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O-octanoyl acetoxime
• 英文别名: propan-2-one O-octanoyl oxime；(Propan-2-ylideneamino) octanoate
• CAS: 116709-88-7
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: UUDDBOIOSMFDCE-UHFFFAOYSA-N

物化性质

• 沸点：
  262.8±23.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-octanoyl acetoxime 、 beta-胸苷 在 Amano PS Lipase 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以82%的产率得到Octanoic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters

  摘要：

  使用肟酯作为酰基转移剂，通过酶促反应可获得 2′-脱氧核苷的 3′-O-酰基衍生物，收率很高。

  DOI：

  10.1055/s-1992-26178
• 作为产物：
  描述：

  辛酰氯 、 丙酮肟 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以878 mg的产率得到O-octanoyl acetoxime
  参考文献：
  名称：

  [EN] NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS
  [FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX

  摘要：

  公开号：

  WO2022217153A3

文献信息

• 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.
• Regioselective Enzymatic Synthesis of Glycerol Derivatives
  作者：G. Aranda、L. Blanco

  DOI：10.1080/00397919208021084

  日期：1992.1

  The regioselective synthesis of 3-acyl-1-(O)-tetradecyl glycerol derivatives was realized by enzymatic transesterification from 1-(O)-tetradecyl glycerol and various acylating reagents. Numerous details on the experimental procedure and isolated 1,3-derivatives are given.
• Gotor, Vicente; Pulido, Rosalino, Journal of the Chemical Society. Perkin transactions I, 1991, # 2, p. 491 - 492
  作者：Gotor, Vicente、Pulido, Rosalino

  DOI：——

  日期：——
• GOTOR, VICENTE;PULIDO, ROSALINO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1991) N, C. 491-492
  作者：GOTOR, VICENTE、PULIDO, ROSALINO

  DOI：——

  日期：——
• MIKROKAPSELZUBEREITUNGEN UND MIKROKAPSELN ENTHALTENDE WASCH- UND REINIGUNGSMITTEL
  申请人：BASF Aktiengesellschaft

  公开号：EP1194521B1

  公开（公告）日：2006-04-12