dibutyl 1,3-acetonedicarboxylate | 42599-01-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: dibutyl 1,3-acetonedicarboxylate
• 英文别名: dibutyl acetonedicarboxylate；3-oxo-pentanedioic acid dibutyl ester；3-oxo-glutaric acid dibutyl ester；3-Oxo-glutarsaeure-dibutylester；Dibutyl 3-oxopentanedioate
• CAS: 42599-01-9
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: SAPPVGOXJLSDHG-UHFFFAOYSA-N

物化性质

• 沸点：
  138-139 °C(Press: 1.0 Torr)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  dibutyl 1,3-acetonedicarboxylate 在 三氧化二氮 、 硝酸 作用下， 生成 2-oxy-furazan-3,4-dicarboxylic acid dibutyl ester
  参考文献：
  名称：

  用于丙酮-1,3-二羧酸二烷基酯和1,3-二乙酰丙酮与氮氧化物的反应

  摘要：

  丙酮-1,3-二羧酸二烷基酯 4a-与一氧化二氮/硝酸反应形成结晶 3,5-二烷氧基羰基-4-氧代-4H-吡唑-1,2-双-氧化物 5a-d 和油状二烷氧基羰基-呋喃烷 6a -D。4e-f 只产生 6e-f。对称的 3,5-diacetyl-4-oxo-4H-pyrazole-1,2-bis-oxide (8) 由 1,3-dacetyl-丙酮 (7) 和四氧化二氮形成。

  DOI：

  10.1002/ardp.19763091003
• 作为产物：
  描述：

  1,3-丙酮二羧酸 、 正丁醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以80 %的产率得到dibutyl 1,3-acetonedicarboxylate
  参考文献：
  名称：

  K2CO3 介导的 1,3-丙酮二羧酸酯与 2-氟-1-硝基芳烃的环化：吲哚的合成

  摘要：

  K 2 CO 3介导的1,3-丙酮二羧酸酯与2当量的一锅反应。取代的 2-氟-1-硝基苯已被开发用于通过串联环化途径合成各种 2,3-二羧酸吲哚。在有效反应中，在开容器条件下形成1个碳-碳双键、1个碳-碳单键和1个碳-氮单键。 DFT 计算用于合理化合理的机制。

  DOI：

  10.1039/d4ob00488d

文献信息

• 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。
• An expedient synthesis of spirooxindoles incorporating 2-amino pyran-3-carbonitrile unit employing dialkyl acetone-1,3-dicarboxylates
  作者：Monisha Satheesh、Aswathy L. Balachandran、Parvathi R. Devi、Ani Deepthi

  DOI：10.1080/00397911.2017.1416143

  日期：2018.3.4

  ABSTRACT Spirooxindoles are a class of molecules possessing significant biological effects such as antiviral, antifungal, antibacterial and anticancer properties. Herein we report a series of spirooxindole molecules having 2-amino pyran-3-carbonitrile and with two ester groups. These molecules were prepared by the reaction of dialkyl acetone-1,3-dicarboxylate and isatilidenes in the presence of triethyl

  摘要 螺环吲哚是一类具有显着生物学效应的分子，如抗病毒、抗真菌、抗菌和抗癌特性。在此我们报告了一系列具有 2-氨基吡喃-3-腈和两个酯基的螺环吲哚分子。这些分子是在三乙胺存在下通过二烷基丙酮-1,3-二羧酸酯和异环丙烷反应制备的。图形概要
• 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。
• Preparation of acetone dicarboxylic acid diester
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0108332A1

  公开（公告）日：1984-05-16

  Disclosed is a process for preparing an acetone dicarboxylic acid diester, which comprises allowing diketene, carbon monoxide and a nitrous acid ester to react with each other in the presence of a palladium halide or a complex thereof.

  本发明公开了一种丙酮二羧酸二酯的制备工艺，该工艺包括让二乙烯、一氧化碳和亚硝酸酯在卤化钯或其络合物的存在下相互反应。