dibenzyl oximinomalonate | 51118-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl oximinomalonate
• 英文别名: Dibenzyl 2-hydroxyiminopropanedioate
• CAS: 51118-40-2
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: YOHOHYXBMNUPOV-UHFFFAOYSA-N

物化性质

• 沸点：
  486.6±48.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dibenzyl oximinomalonate 在 aluminum amalgam 、 sodium hydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 82.0h， 生成 9a-benzyloxycarbonyl-2-methyl-1,4-dioxo-octahydropyrido[1,2-a]pyrazine
  参考文献：
  名称：

  The synthetic versatility of alkoxycarbonyl- and hydroxymethyl-piperazine-2,5-diones

  摘要：

  Alkoxycarbonylpiperazine-2,5-diones are versatile precursors for the alpha-functionalisation of piperazine-2,5-diones. The alkoxycarbonyl group activates the a-carbon position to alkylation reactions and this provides a mild and selective method for the extension of the carbon framework of piperazine-2,5-diones. In addition, the alkoxycarbonyl group can be converted to the carboxy group, which in turn can be 'deleted' or manipulated for the installation of carbon and/or heteroatom substituents where desired, the latter via N-acyliminium chemistry. We also demonstrate that hydroxymethylpiperazine-2,5-diones complement carboxypiperazinediones as precursors for the generation of N-acyliminium ions. (c) 2005 Elsevier Ltd. All-rights reserved.

  DOI：

  10.1016/j.tet.2005.06.084
• 作为产物：
  描述：

  二苄基马来酸酯 在 盐酸 、 亚硝酸丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 17.0h， 以36%的产率得到dibenzyl oximinomalonate
  参考文献：
  名称：

  通过DAST 介导的α-肟基-β-酮酯的C C 键裂解合成氰基甲酸酯

  摘要：

  使用简单的β-酮酯作为底物开发了一种合成氰基甲酸酯的新方案。（二乙氨基）三氟化硫 (DAST) 用作双重作用试剂以激活肟部分并提供氟化物。关键中间体，α -oximino- β酮酯中，通过高效的酸辅助肟化制备β酮酯。然后，证明了通过氟化 C C 键断裂对α-肟基-β-酮酯的解构提供了氰甲酸酯。在这种情况下，氟化物添加后 CC 键断裂选择性地发生在酮中而不是酯中。由于简单和温和的反应条件，举例说明了各种功能化的氰基甲酸酯。

  DOI：

  10.1016/j.tetlet.2021.153116

文献信息

• The Synthesis and Application of Novel Nitrating and Nitrosating Agents
  作者：Gholam H. Hakimalahi、Hashem Sharghi、Hamide Zarrinmayeh、Ali Khalafi-Nezhad

  DOI：10.1002/hlca.19840670332

  日期：1984.5.2

  Alcohols and phenols are efficiently nitrated with thionyl chloride nitrate or thionyl nitrate, even in the presence of an aromatic moiety. While thionyl chloride nitrate is suitable for nitration of primary OH-groups in carbohydrates, thionyl nitrate is reactive enough to react with secondary OH-groups as well. These reagents permit the highly selective nitration of the 5′-,2′5′- and 3′, 5′-OH-groups

  即使在存在芳族部分的情况下，醇和苯酚也可以被硝酸亚硫酰氯或硝酸亚硫酰有效地硝化。硝酸亚硫酰氯适用于碳水化合物中伯羟基的硝化，而硝酸亚硫酰具有足够的反应性，可以与仲羟基反应。这些试剂允许核糖核苷的5'-，2'5'-和3'，5'-OH-基团的高选择性硝化，以高产率产生单保护或双保护的硝基衍生物。碳酸和某些酮的烯醇形式可以用三氟甲磺酰硝酸盐/叔丁醇钾有效地硝化。Lutidine N -oxide（2,6-（CH 3）2 C 5 H 3发现NO）对硝化反应具有显着影响。类似地，亚硫酰氯亚硝酸盐和亚硫酰亚硝酸盐显示出优异的上述底物的亚硝化能力。
• Synthetic and biosynthetic studies of porphyrins. Part 8. Syntheses of hepta-, hexa-, and penta-carboxylic porphyrins related to uroporphyrin-I
  作者：Anthony H. Jackson、Damrus Supphayen

  DOI：10.1039/p19870000277

  日期：——

  The title porphyrins, of interest as abnormal metabolites in porphyrin biosynthesis, have been synthesized by the Fischer, and b-oxobilane routes, and compared with the naturally derived materials. Enzymic experiments have shown that the conversion of uroporphyrinogen-I into coproporphyrinogen-I both in vivo and in vitro is non-specific and occurs by both possible pathways via the two intermediate

  标题卟啉，作为卟啉生物合成中的异常代谢产物，已经通过费歇尔和b-氧杂环丁烷路线合成，并与天然物质进行了比较。酶学实验表明，尿卟啉原-I在体内和体外的转化都是非特异性的，并且通过两种中间的六羧酸卟啉原通过两种可能的途径发生。
• Investigations regarding the utility of prodigiosenes to treat leukemia
  作者：Deborah A. Smithen、A. Michael Forrester、Dale P. Corkery、Graham Dellaire、Julie Colpitts、Sherri A. McFarland、Jason N. Berman、Alison Thompson

  DOI：10.1039/c2ob26535d

  日期：——

  Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against leukemia cell lines during in vitro analysis against the NCI 60 cancer cell line panel. Further in vivo studies of these compounds using the zebrafish model showed persistence of anti-leukemia properties in human K562 chronic myelogenous leukemia cells.

  灵菌烯具有 4-甲氧基吡咯基二吡林骨架，以其抗癌活性而闻名。 C 环的结构修饰产生了一系列灵菌烯，在针对 NCI 60 癌细胞系组的体外分析中，这些灵菌烯显示出针对白血病细胞系的有希望的活性。使用斑马鱼模型对这些化合物进行的进一步体内研究表明，在人类 K562 慢性粒细胞白血病细胞中具有持久的抗白血病特性。
• Synthesis and anticancer activity of prodigiosenes bearing C-ring esters and amides
  作者：Kate-lyn A. R. Lund、Carlotta Figliola、Aleksandra K. Kajetanowicz、Alison Thompson

  DOI：10.1039/c7ra01628j

  日期：——

  Prodigiosenes, a class of compounds characterised by their 4-methoxypyrrolyldipyrrin framework, are known to possess anti-cancer activity. Structural modification of the C-ring of prodigiosenes presented ten new prodigiosenes bearing pendant alkyl esters and amides. These prodigiosenes were evaluated biologically and displayed notable anticancer in vitro activity, particularly when featuring a hexyl

  dig烯，以其4-甲氧基吡咯烷基二吡喃骨架为特征的一类化合物，已知具有抗癌活性。dig的C-环的结构修饰提出了十个带有侧链烷基酯和酰胺的新的dig。通过生物学评估了这些pro，并显示出显着的体外抗癌活性，尤其是在具有己基链的情况下。
• Total synthesis of cyclopentenoporphyrins of sedimentary origin: deoxophylloerythroetioporphyrin, chlorophyll c fossils and related compounds.
  作者：Claude Bauder、Rubén Ocampo、Henry J. Callot

  DOI：10.1016/s0040-4020(01)90123-1

  日期：1992.1

  This article describes the total synthesis of seven porphyrins, fossils of chlorophyll derivatives, isolated from sedimentary sources and possess five-membered rings fused to the porphyrin nucleus, this additional ring being placed between positions 13,15 or 15,17. This ring was built from vinyl, hydroxyethyl or isopropenyl groups under strong acidic conditions.