dibenzyl 1,3-acetonedicarboxylate | 28009-82-7

• 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 1,3-acetonedicarboxylate
• 英文别名: Dibenzyl 3-oxopentanedioate
• CAS: 28009-82-7
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: SWXXORGMUFCOHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dibenzyl 1,3-acetonedicarboxylate 在 2-chloro-1,3-dimethyl imidazolium chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到dibenzyl 2,3-pentadienedioate
  参考文献：
  名称：

  DMC合成1,3-二羧酸Allene的新方法和串联环化成吡咯烷核生物碱骨架的新方法

  摘要：

  通过使用DMC作为脱水试剂，高产率地从1,3-二羧酸丙酮中合成了1,3-二羧酸Allene-1。此过程开辟了一条新的快速途径，即通过迈克尔加成反应和新颖的串联环化反应，从1,3-二羧酸二甲酯和双（2-氯乙基）胺合成吡咯烷核生物碱的1-azabicyclo [3.3.0]辛烷骨架。

  DOI：

  10.1016/s0040-4039(98)01344-6
• 作为产物：
  描述：

  丙二酸单苯甲酯 在 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以82%的产率得到dibenzyl 1,3-acetonedicarboxylate
  参考文献：
  名称：

  活化丙二酸半酯的自缩合：聚酮化合物生物合成中脱羧性克莱森缩合的模型

  摘要：

  丙二酸半含氧酸酯与N-羟基琥珀酰亚胺基酯形成试剂的反应导致自缩合，从而提供相应的1，3-丙酮二羧酸二酯。此新方法不需要二价金属螯合剂或配位溶剂即可成功缩合。

  DOI：

  10.1016/j.tetlet.2003.08.014

文献信息

• SUBSTITUTED OXOPYRIDINE DERIVATIVES
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160272637A1

  公开（公告）日：2016-09-22

  The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and oedemas, and also ophthalmic disorders.

  这项发明涉及替代的氧代吡啶衍生物及其制备方法，以及它们用于制备用于治疗和/或预防疾病的药物，特别是心血管疾病，优选为血栓性或血栓栓塞性疾病，水肿，以及眼科疾病。
• A HTS Assay for the Detection of Organophosphorus Nerve Agent Scavengers
  作者：Ludivine Louise-Leriche、Emilia Pǎunescu、Géraldine Saint-André、Rachid Baati、Anthony Romieu、Alain Wagner、Pierre-Yves Renard

  DOI：10.1002/chem.200902986

  日期：2010.3.15

  at a HTS assay of scavengers is able to selectively and efficiently cleave the PS bond of organophosphorus nerve agents and by this provides non‐toxic phosphonic acid has been designed and synthesised. The previously described pro‐fluorescent probes were based on a conventional activated POaryl bond cleavage, whereas our approach uses a self‐immolative linker strategy that allows the detection of phosphonothioase

  一种针对清除剂的HTS分析的新型前荧光探针能够选择性和有效地裂解有机磷神经毒剂的PS键，从而设计并合成了无毒的膦酸。先前描述的亲荧光探针是基于传统的活性P  O芳基键裂解，而我们的方法使用自脱落接头策略，其允许phosphonothioase活性的检测相对于非活化的P  1-8烷基键。此外，我们还开发并优化了高通量筛选分析方法，以选择可以有效水解高毒性V的去污剂（化学或生物化学清除剂）。型神经毒剂。在一个小的α-亲核试剂库上进行的初步筛选使我们能够鉴定出一些初步的“命中”，其中吡啶醛肟，α-氧代肟，异羟肟酸和活性较低但较原始的a胺肟是最有前途的。通过使用PhX作为底物进一步证实了它们的选择性磷酸硫代磷酸酶活性，因此它们为合成更有效的V神经剂清除剂提供了新的见解。
• Process for producing optically active tropinonemonocarboxylic acid derivative
  申请人：Nihon Medi-Physics Co., Ltd.

  公开号：US06486323B1

  公开（公告）日：2002-11-26

  An optically active tropinonemonocarboxylic acid ester derivative useful as an intermediate for synthesis of optically active tropane derivatives was obtained by reacting succindialdehyde with an organic amine and acetonedicarboxylic acid ester to obtain a tropinonedicarboxylic acid ester derivative, and then subjecting this derivative to enzyme-catalyzed asymmetric dealkoxy-carbonylation. Since anhydroecgonine methyl ester derived from the optically active tropinone-monocarboxylic acid ester derivative by reduction and dehydration had the same direction of optical rotation as in the case of anhydroecgonine methyl ester obtained from natural cocaine, it was proved that the obtained optically active tropinonemonocarboxylic acid ester derivative had the same absolute configuration as that of natural cocaine. The yield of the optically active tropinonemonocarboxylic acid ester derivative from the asymmetric dealkoxycarbonylation was 30 to 50 mol %, and its optical purity was 70 to 97% ee. In addition, it was found that a crystalline optically active anhydroecgonine carboxylic acid ester derivative can be obtained by reducing and then dehydrating the optically active tropinonemonocarboxylic acid ester derivative and that its optical purity can easily be increased by recrystallization.

  通过将琥珀醛与有机胺和乙二酸二甲酯反应，得到了一种具有光学活性的环戊酮单羧酸酯衍生物，可用作合成具有光学活性的托帕甲基衍生物的中间体。然后将这种衍生物经过酶催化的不对称去烷氧羰基化，得到了一种环戊酮二羧酸酯衍生物。由于通过还原和脱水得到的光学活性环戊酮单羧酸酯衍生物衍生的无水异恶康宁甲酯的旋光方向与从天然可卡因中获得的无水异恶康宁甲酯相同，证明所得的光学活性环戊酮单羧酸酯衍生物具有与天然可卡因相同的绝对构型。从不对称去烷氧羰基化中得到的光学活性环戊酮单羧酸酯衍生物的产率为30至50摩尔％，其光学纯度为70至97％ee。此外，发现可以通过还原然后脱水光学活性环戊酮单羧酸酯衍生物，得到结晶的光学活性无水异恶康宁羧酸酯衍生物，并且通过再结晶可以轻松提高其光学纯度。
• A convenient method for the synthesis of 3,6-dihydroxy-benzene-1,2,4,5-tetracarboxylic acid tetraalkyl esters and a study of their fluorescence properties
  作者：Aswathy L. Balachandran、Vidya Sathi、Ani Deepthi、Chettiyam V. Suneesh

  DOI：10.3998/ark.5550190.p009.843

  日期：——

  A mild, efficient and simple method for the synthesis of 3,6-dihydroxy-1,2,4,5-tetracarboxylic tetraalkyl esters using cerium(IV) ammonium nitrate mediated oxidation of 1,3-acetone dicarboxylates has been developed. The detailed absorption and emission studies of the synthesized compounds reveal that these molecules have appreciable quantum yields and possess large Stokes shift values.

  已开发出一种温和、高效且简单的方法，用于使用硝酸铈 (IV) 铵介导的 1,3-丙酮二羧酸酯氧化合成 3,6-二羟基-1,2,4,5-四羧酸四烷基酯。合成化合物的详细吸收和发射研究表明，这些分子具有可观的量子产率和大斯托克斯位移值。
• Process for producing optically active tropinonemonocarboxylic acid ester derivative
  申请人：NIHON MEDI-PHYSICS CO., LTD.

  公开号：US20030065183A1

  公开（公告）日：2003-04-03

  An optically active tropinonemonocarboxylic acid ester derivative useful as an intermediate for synthesis of optically active tropane derivatives was obtained by reacting succindialdehyde with an organic amine and acetonedicarboxylic acid ester to obtain a tropinonedicarboxylic acid ester derivative, and then subjecting this derivative to enzyme-catalyzed asymmetric dealkoxy-carbonylation. Since anhydroecgonine methyl ester derived from the optically active tropinone-monocarboxylic acid ester derivative by reduction and dehydration had the same direction of optical rotation as in the case of anhydroecgonine methyl ester obtained from natural cocaine, it was proved that the obtained optically active tropinonemonocarboxylic acid ester derivative had the same absolute configuration as that of natural cocaine. The yield of the optically active tropinonemonocarboxylic acid ester derivative from the asymmetric dealkoxycarbonylation was 30 to 50 mol %, and its optical purity was 70 to 97% ee. In addition, it was found that a crystalline optically active anhydroecgonine carboxylic acid ester derivative can be obtained by reducing and then dehydrating the optically active tropinonemonocarboxylic acid ester derivative and that its optical purity can easily be increased by recrystallization.

  通过将琥珀二醛与有机胺和乙酰二羧酸酯反应得到了一种光学活性的茎叶酮单羧酸酯衍生物，可用作合成光学活性茎曲烷衍生物的中间体。然后将这种衍生物经过酶催化的不对称脱醚羰基化反应。通过还原和脱水，从光学活性的茎叶酮单羧酸酯衍生物得到的无水异甘氨酸甲酯旋光方向与从天然可卡因中获得的无水异甘氨酸甲酯相同，证明获得的光学活性茎叶酮单羧酸酯衍生物具有与天然可卡因相同的绝对构型。从不对称脱醚羰基化反应中得到的光学活性茎叶酮单羧酸酯衍生物的产率为30至50摩尔％，其光学纯度为70至97％ ee。此外，还发现通过还原然后脱水，可以获得结晶的光学活性无水异甘氨酸羧酸酯衍生物，并且可以通过重结晶轻松提高其光学纯度。