acetone oxime decanoate | 133360-57-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: acetone oxime decanoate
• 英文别名: (Propan-2-ylideneamino) decanoate
• CAS: 133360-57-3
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: MFXBVHGYDLDDCE-UHFFFAOYSA-N

物化性质

• 沸点：
  298.5±23.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  acetone oxime decanoate 、 尿嘧啶核苷 以 四氢呋喃 为溶剂， 反应 4.0h， 以96%的产率得到5′-O-(decanoyl)uridine
  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：

  正癸酸 、 丙酮肟 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到acetone oxime decanoate
  参考文献：
  名称：

  糖脂库的化学酶法合成和抗原表位的阐明，用于构建针对莱姆病的疫苗

  摘要：

  莱姆病（LD）是欧洲，北美和亚洲最常见的壁虱传播疾病。LD的病原体是Borrelia burgdorferi sensu lato组的螺旋体，其脂质含量为干重的25–30％。主要糖脂胆固醇6- ö酰基-β- d -galactopyranoside（ACGal），存在于博氏疏螺旋狭义，B. afzelii，和B. garinii，是一种特异且高度流行的抗原，经常被晚期LD的抗体识别。在这里，我们报告了通过化学合成步骤与酶促转化相结合的化学合成ACGal的便捷途径。通过用患者血清进行免疫印迹将该合成的分子与细菌提取物进行比较，确认了保留的抗原性。接下来，设计并合成了衍生自具有脂肪酰基部分变化的天然分子的糖脂文库和其中胆固醇已被取代的衍生物。化学结构通过1D和2D NMR光谱法和质谱法确认。将天然和合成的糖脂用于免疫印迹，以确定患者血清中抗体识别的表位。通过这种方法，我们可以证明半乳糖 胆固醇

  DOI：

  10.1002/chem.200902205

文献信息

• Towards the selective acylation of secondary hydroxyl groups of carbohydrates using oxime esters in an enzyme-catalyzed process
  作者：Rosalino Pulido、Vicente Gotor

  DOI：10.1016/0008-6215(94)90005-1

  日期：1994.1

  alkyloxycarbonylation. A lipase from Pseudomonas cepacia catalyzed also the regioselective acylation of the primary hydroxyl group of 1 and 2 when 1,4-dioxane was used as solvent. Moreover, this lipase was a suitable biocatalyst for the acylation of the secondary HO-3 of 6- O (benzyloxy)carbonyl derivatives of 2-deoxy- d -hexoses. Subsequent deprotection of the primary hydroxyl group through catalytic hydrogenation

  摘要使用南极假丝酵母的脂肪酶，以肟酯为肟基，对2-脱氧-d-阿拉伯-己基吡喃糖（1）和2-脱氧-d-lyxo-己基吡喃糖（2）基团的伯羟基进行区域选择性酰化和烷氧基羰基化。酰化剂。吡啶和1,4-二恶烷均用作酰化过程中的溶剂，但只有1,4-二恶烷对烷氧基羰基化有效。当将1，4-二恶烷用作溶剂时，来自洋葱假单胞菌的脂肪酶还催化1和2的伯羟基的区域选择性酰化。此外，该脂肪酶是用于2-脱氧-d-己糖的6-O（苄氧基）羰基衍生物的仲HO-3的酰化的合适的生物催化剂。随后通过催化氢化使伯羟基脱保护，容易得到1和2的3-O-酰基衍生物。还报道了通过上述脂肪酶对1，6-脱水-β-d-吡喃葡萄糖的区域选择性酰化和烷氧基羰基化的研究。
• Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters
  作者：Vicente Gotor、Francisco Morís

  DOI：10.1055/s-1992-26178

  日期：——

  3′-O-Acyl derivatives of 2′-deoxynucleosides are obtained in good yield through an enzymatic reaction using oxime esters as acyl transfer agents.

  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。
• Pulido, Rosalino; Ortiz, Fernando Lopez; Gotor, Vicente, Journal of the Chemical Society. Perkin transactions I, 1992, # 21, p. 2891 - 2898
  作者：Pulido, Rosalino、Ortiz, Fernando Lopez、Gotor, Vicente

  DOI：——

  日期：——
• 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：——