Acetoneoxime chloroacetate | 20606-16-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Acetoneoxime chloroacetate
• 英文别名: 2-chloroacetic acid acetone oxime ester；acetone O-(2-chloroacetyl)oxime；(Propan-2-ylideneamino) 2-chloroacetate
• CAS: 20606-16-0
• 化学式: C₅H₈ClNO₂
• mdl: MFCD19235563
• 分子量: 149.577
• InChiKey: ONTKCAXGLKNDGW-UHFFFAOYSA-N

物化性质

• 沸点：
  178.7±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  Acetoneoxime chloroacetate 、 尿嘧啶核苷 以 四氢呋喃 为溶剂， 反应 24.0h， 以90%的产率得到5'-O-Chloracetyluridin
  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：

  氯乙酰氯 、 丙酮肟 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 Acetoneoxime chloroacetate
  参考文献：
  名称：

  含1,2,4-三唑或1,3,4-恶二唑部分的肟酯衍生物的合成及抑菌活性

  摘要：

  摘要设计并合成了一系列含有1,2,4-三唑或1,3,4-恶二唑部分的肟酯衍生物，它们在体外对轴突黄单胞菌pv具有抗菌活性。柠檬（Xac）和米黄单胞菌（Xanthomonas oryzae）。评估稻米（Xoo）。生物测定表明，所有标题化合物均显示出对Xac和Xoo的有效抗菌活性。尤其是，化合物4a，5a，5b，5c，5d，5h和5i在EC 50的情况下对Xoo表现出显着的抗菌活性。值范围从15.15至49.34μg/ mL，优于比美噻唑（92.61μg/ mL）。这项研究表明，含有1,2,4-三唑或1,3,4-恶二唑部分的肟酯衍生物可以用作寻找新型抗菌剂的潜在替代模板。 图形概要

  DOI：

  10.1007/s11696-017-0189-5

文献信息

• 含羧酸肟脂的1,2,4-三唑类化合物、其制备方 法及应用
  申请人：贵州大学

  公开号：CN105837523B

  公开（公告）日：2018-09-11

  本发明公开了一种含羧酸肟脂的1,2,4‑三唑类化合物、其制备方法及应用，其结构通式(I)如下：R为苯基、4‑氟苯基、4‑氯苯基、4‑三氟甲基苯基、4‑硝基苯基、4‑甲氧基苯基、3,4‑二甲氧基苯基、3,4,5‑三甲氧基苯基；R1为甲基、乙基；R2为甲基。本发明在抑制柑橘溃疡病菌、烟草青枯病菌及水稻白叶枯病菌方面有着较好的生物活性。
• 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.
• Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety
  作者：Xiaobin Wang、Xinmin Zhong、Xuesong Zhu、Hua Wang、Qin Li、Juping Zhang、Xianghui Ruan、Wei Xue

  DOI：10.1007/s11696-017-0189-5

  日期：2017.10

  ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activities in vitro against Xanthomonas axonopodis pv. citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were evaluated. The bioassays showed that all the title compounds exhibit potent antibacterial activity against Xac and Xoo. In particular, the compounds 4a, 5a, 5b, 5c,

  摘要设计并合成了一系列含有1,2,4-三唑或1,3,4-恶二唑部分的肟酯衍生物，它们在体外对轴突黄单胞菌pv具有抗菌活性。柠檬（Xac）和米黄单胞菌（Xanthomonas oryzae）。评估稻米（Xoo）。生物测定表明，所有标题化合物均显示出对Xac和Xoo的有效抗菌活性。尤其是，化合物4a，5a，5b，5c，5d，5h和5i在EC 50的情况下对Xoo表现出显着的抗菌活性。值范围从15.15至49.34μg/ mL，优于比美噻唑（92.61μg/ mL）。这项研究表明，含有1,2,4-三唑或1,3,4-恶二唑部分的肟酯衍生物可以用作寻找新型抗菌剂的潜在替代模板。 图形概要