丙酮O-<(乙烯氧基)羰基>肟 | 139705-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 丙酮O-<(乙烯氧基)羰基>肟
• 英文名称: acetone O-[(vinyloxy)carbonyl]oxime
• 英文别名: Ethenyl (propan-2-ylideneamino) carbonate
• CAS: 139705-38-7
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: DNFOKRIHYIUHBR-UHFFFAOYSA-N

物化性质

• 沸点：
  160.1±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙酮O-<(乙烯氧基)羰基>肟 、 卡那霉素 B 以 phosphate buffer 为溶剂， 反应 5.0h， 以84%的产率得到
  参考文献：
  名称：

  Chemoenzymatic Synthesis and High-Throughput Screening of an Aminoglycoside−Polyamine Library:  Identification of High-Affinity Displacers and DNA-Binding Ligands

  摘要：

  Chemoenzymatic parallel synthesis and high-throughput screening were employed to develop a multivalent aminoglycoside-polyamine library for use as high-affinity cation-exchange displacers and DNA-binding ligands. Regioselective lipase-catalyzed acylation, followed by chemical aminolysis, was used to generate vinyl carbonate and vinyl carbamate linkers, respectively, of the aminoglycosidic cores. These were further derivatized with polyamines, leading to library generation. A parallel batch-displacement assay was employed to identify the efficacy of the library candidates as potential displacers for protein purification. Using this approach, low-molecular-mass displacers with affinities higher than those previously observed have been identified. The aminoglycoside-polyamine library was also screened for DNA binding efficacy using an ethidium bromide displacement assay. These highly cationic molecules exhibited strong DNA-binding properties and may have potential for enhanced gene delivery.

  DOI：

  10.1021/ja049437n
• 作为产物：
  描述：

  氯甲酸乙烯酯 、 丙酮肟 生成 丙酮O-<(乙烯氧基)羰基>肟
  参考文献：
  名称：

  Lipase-mediated alkoxycarbonylation of nucleosides with oxime carbonates.

  摘要：

  5'-O-carbonates of ribonucleosides and 2'-deoxyribonucleosides could be obtained by enzymatic alkoxycarbonylation with SP 435 lipase (from Candida antarctica) and oxime carbonates, which are easily prepared from chloroformates. Ribonucleosides gave as result two kind of 5'-O-carbonates depending on whether alkoxy or acetone oxime moiety acted as the leaving group. In the case of 2-deoxynucleosides, the leaving group was always the acetonoxime moiety, giving rise to regioselective formation of the corresponding 5'-O-alkyl carbonates, together with small amounts of 3'-O-regiosiomer and diacylated compounds.

  DOI：

  10.1016/s0040-4020(01)92279-3

文献信息

• Synthesis of Purine and Pyrimidine 3‘-Amino-3‘-deoxy- and 3‘-Amino-2‘,3‘-dideoxyxylonucleosides
  作者：Luis F. García-Alles、Julia Magdalena、Vicente Gotor

  DOI：10.1021/jo9606259

  日期：1996.1.1

  A general procedure to obtain the 3'-aminoxylonucleosides 13a,b and 17a,b is presented. The synthetic scheme is based on the 5' directed intramolecular nucleophilic substitution at the 3'-activated position of the nucleoside. The approach of the incoming group to this position takes place regio- and stereoselectively from the most hindered face of the nucleoside. The methodology presented is applicable

  提出了获得3'-氨基木糖核苷13a，b和17a，b的一般方法。合成方案基于在核苷的3'活化位置的5'定向分子内亲核取代。进入的基团到达该位置的途径是从核苷的最受阻表面区域性和立体选择性地发生的。提出的方法学适用于核糖核苷和2'-脱氧核糖核苷，无论它们的碱基是否已硝化。
• Chemo-enzymatic synthesis of 2′-deoxynucleoside urethanes
  作者：Luis F. García-Alles、Francisco Morís、Vicente Gotor

  DOI：10.1016/s0040-4039(00)73746-4

  日期：1993.9

  2′-Deoxynucleoside 5′- and 3′-(N-alkyl) carbamates were synthesized in a two step procedure, asing lipases to catalyze the first regioselective vinyloxycarbonylation step.

  以两步法合成2′-脱氧核苷5′-和3′-（N-烷基）氨基甲酸酯，用脂肪酶催化第一区域选择性乙烯基氧羰基化步骤。
• CAL-B-Catalyzed Alkoxycarbonylation of A-Ring Stereoisomeric Synthons of 1α,25-Dihydroxyvitamin D₃ and 1α,25-Dihydroxy-19-<i>nor</i>-previtamin D₃:  A Comparative Study. First Regioselective Chemoenzymatic Synthesis of 19-<i>nor</i>-A-Ring Carbonates
  作者：Mónica Díaz、Vicente Gotor-Fernández、Miguel Ferrero、Susana Fernández、Vicente Gotor

  DOI：10.1021/jo010017f

  日期：2001.6.1

  took place at the C-5-(R) or C-5-(S) hydroxyl groups. However, if the chiral centers at C-3 are (R), CAL-B alkoxycarbonylated the C-3-(R) hydroxyl group independently of the configuration at C-5. The corresponding carbonates are useful A-ring precursors of 1alpha,25-dihydroxyvitamin D3 analogues, selectively modified at the C-1 or C-3 positions. In addition, an improved synthesis of cis A-ring synthons

  已描述了由南极假丝酵母脂肪酶B（CAL-B）催化的1alpha，25-二羟基维生素D3类似物的19-nor-A-环和A-环立体异构体的烷氧基羰基化过程的比较研究。如在3-6中一样，在C-2的A环中甲基的存在对生物催化的区域选择性具有决定性作用，主要是使C-5位置的羟基反应。对于缺少C-2甲基的19-nor-A环立体异构体7-10，C-3和C-5处的构型对CAL-B表现出的选择性有很大影响。因此，取决于C-3构型，每对对映异构体显示相反的区域选择性。当C-3具有（S）-构型时，在C-5-（R）或C-5-（S）羟基上发生酶促烷氧基羰基化。但是，如果C-3的手性中心为（R），CAL-B烷氧基羰基独立于C-5处的构型而对C-3-（R）羟基进行了处理。相应的碳酸盐是有用的1α，25-二羟基维生素D3类似物的A环前体，可在C-1或C-3位置进行选择性修饰。另外，使用Mitsunobu方法描述了改进的顺式A环合成子5和6的合成。
• Aminoglycoside-polyamine displacers and methods of use in displacement chromatography
  申请人：Rege Kaushal

  公开号：US20070049741A1

  公开（公告）日：2007-03-01

  Aminoglycoside-polyamines are disclosed along with methods of use thereof in displacement chromatography and as DNA-binding ligands. The aminoglycoside-polyamines are derivatives of carbohydrates, such as sugars, amino sugars, deoxysugars, glycosides, nucleosides and their substituted counterparts. The subject polyamines possess a group in place of at least one hydrogen atom of at least one hydroxyl group of the carbohydrate compound. In these compounds R 1 is an alkyl group or an azaalkyl group, and R 2 is a primary or secondary amino group.

  本文披露了氨基糖苷-多胺以及它们在置换色谱和作为DNA结合配体中的使用方法。氨基糖苷-多胺是碳水化合物的衍生物，例如糖，氨基糖，去氧糖，糖苷，核苷和它们的取代物。这些多胺具有取代至少一种碳水化合物化合物的至少一个羟基的氨基团。在这些化合物中，R1是烷基或氮杂基，R2是一级或二级氨基。
• Selective Alkoxycarbonylation of A-Ring Precursors of Vitamin D Using Enzymes in Organic Solvents. Chemoenzymatic Synthesis of 1α,25-Dihydroxyvitamin D₃ C-5 A-Ring Carbamate Derivatives¹
  作者：Miguel Ferrero、Susana Fernández、Vicente Gotor

  DOI：10.1021/jo970133b

  日期：1997.6.1

  of vitamin D-related structures. An efficient synthesis of 1alpha,25-(OH)(2)-D(3) C-5 A-ring carbamate derivatives 19 and amino acid derivatives 21 was developed by applying a two-step chemoenzymatic strategy, involving the enzymatic synthesis of carbonates followed by reaction with amino derivatives. Accordingly, we began the studies of enzymatic alkoxycarbonylation of 1alpha,25-(OH)(2)-D(3) A-ring

  A环修饰的1alpha，25-dihydroxyvitamin D（3）[2，1alpha，25-（OH）（2）-D（3）]是模拟研究的重要领域，以研究维生素D相关结构的生物活性。有效的合成1alpha，25-（OH）（2）-D（3）C-5 A环氨基甲酸酯衍生物19和氨基酸衍生物21通过应用两步化学酶催化策略，涉及碳酸盐的酶促合成然后与氨基衍生物反应。因此，我们开始了1α，25-（OH）（2）-D（3）A环前体7的酶法烷氧基羰基化的研究。发现南极假丝酵母脂肪酶（CAL）是甲苯中的最佳催化剂。区域选择性烷氧基羰基化仅在C-5-（R）羟基上发生。通过使这些碳酸盐与氨基衍生物进行化学反应，可以实现良好的优良收率。