di-i-propyl 2-oxo-pentandioate | 78266-99-6

• 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: di-i-propyl 2-oxo-pentandioate
• 英文别名: oxo-2 glutarate d'isopropyle；diisopropyl 2-oxoglutarate；Dipropan-2-yl 2-oxopentanedioate
• CAS: 78266-99-6
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: HYVSVZYBKWNFEU-UHFFFAOYSA-N

物化性质

• 沸点：
  304.1±25.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  di-i-propyl 2-oxo-pentandioate 在 三乙氧基硅烷 、 cesium fluoride 作用下， 反应 0.5h， 以70%的产率得到(+/-)-di-i-propyl 2-hydroxypentandioate
  参考文献：
  名称：

  通过盐表面上的非均相催化选择性还原羰基化合物

  摘要：

  由KF和CsF活化的（EtO）3 SiH和Me（EtO）2 SiH是有效的选择剂，用于羰基的异质还原。

  DOI：

  10.1039/c39810000121
• 作为产物：
  描述：

  alpha-酮戊二酸 、 异丙醇 生成 di-i-propyl 2-oxo-pentandioate
  参考文献：
  名称：

  还原选择性地由羰基组成的催化异质表面

  摘要：

  用乙氧基氢硅烷和碱金属氟化物作为催化剂而没有溶剂进行的羰基化合物的还原是高度选择性的。反应顺序为醛>酮>酯。在酮存在下，醛的还原是可能的，在酯存在下，酮的还原是可能的。酮酯中的酮基可以被选择性地还原。该系统的高选择性归因于三个因素：氢硅烷反应性（EtO）2 SiMeH <（EtO）3 SiH），盐的性质（KF

  DOI：

  10.1016/s0040-4020(01)97975-x

文献信息

• PdII-Catalyzed Conjugate Addition of Boronic Acids to Ketoglutaconic Esters toward the Synthesis of Functionalized Pyridazin-3(2H)-ones with Neuroprotective Activity
  作者：Silvia Roscales、Andrea Ortega、Sagrario Martín-Aragón、Paloma Bermejo-Bescós、Aurelio G. Csákÿ

  DOI：10.1002/ejoc.201200734

  日期：2012.9

  The development of the regioselective conjugate addition of boronic acids to ketoglutaconic esters under transition metal catalysis is reported. Among the different catalysts tested for this transformation, the dicationic PdII catalysts generated with Pd(OCOCF3)2, dppben, and HBF4 performed best in terms of yields, regioselectivities and avoidance of Heck-type by-products. The resulting 4-aryl-2-oxopentadienoates

  报道了在过渡金属催化下硼酸与酮戊二酸酯的区域选择性共轭加成的发展。在为这种转化测试的不同催化剂中，用 Pd(OCOCF3)2、dppben 和 HBF4 生成的双阳离子 PdII 催化剂在产率、区域选择性和避免 Heck 型副产物方面表现最好。由此产生的 4-aryl-2-oxopentadienoates 转化为哒嗪-3(2H)-ones，可能用于治疗神经退行性疾病。这些化合物同时表现出 β-分泌酶活性、抑制 β-淀粉样蛋白 (βA) 聚集和分解预先形成的 βA 原纤维，并且还具有良好的细胞内活性氧 (ROS) 清除能力。
• Enantioselective Pictet–Spengler Condensation to Access the Total Synthesis of (+)‐Tabertinggine
  作者：Dan Long、Gaoyuan Zhao、Zhiqiang Liu、Peiqi Chen、Shiqiang Ma、Xingang Xie、Xuegong She

  DOI：10.1002/ejoc.202200088

  日期：2022.3.15

  An effective catalytic enantioselective Pictet–Spengler condensation/intramolecular lactamization cascade reaction to construct the tetracyclic lactam is presented, and the total synthesis of (+)-tabertinggine was obtained.

  提出了一种有效的催化对映选择性Pictet-Spengler缩合/分子内内酰胺化级联反应来构建四环内酰胺，并获得了(+)-tabertinggine的全合成。
• Polymer‐Supported Phosphoric‐Acid Catalysed Enantioselective Pictet‐Spengler Cyclisation for the Synthesis of Quaternary Tryptolines in Batch/Continuous Flow
  作者：Moreshwar B. Chaudhari、Prachi Gupta、Patricia Llanes、Miquel A. Pericàs

  DOI：10.1002/adsc.202201275

  日期：2023.2.21

  the reaction has been demonstrated in continuous flow, with a residence time of only 24 minutes. The robust immobilized catalyst has been recycled and reused multiple times in batch and flow. The synthesis of the chiral precursors of Tadalafil, the Iboga-type alkaloid (+)-Tabertinggine and antimalarial spiroindolinones has been achieved in batch and continuous-flow.

  由聚合物支持的磷酸 (TRIP) 催化的色胺和二酮化合物的对映选择性 Pictet-Spenlger 反应首次在连续流动中完成。使用这种方法，以 36-95% 的收率和 39-99% 的对映体过量合成了一个多样化的四元色氨酸文库。反应的可扩展性已在连续流中得到证明，停留时间仅为 24 分钟。坚固的固定化催化剂已分批和流动多次回收和重复使用。他达拉非的手性前体、Iboga 型生物碱 (+)-Tabertinggine 和抗疟药螺吲哚啉酮的合成已经实现了分批和连续流。
• Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
  作者：Sara Drioli、Patrizia Nitti、Giuliana Pitacco、Laura Tossut、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00286-4

  日期：1999.7

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
  作者：Eduardo M. Rustoy、Elba N. Pereyra、Silvia Moreno、Alicia Baldessari

  DOI：10.1016/j.tetasy.2004.10.013

  日期：2004.11

  An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantionterically pure 3-carboxyalkyl-gamma-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-gamma-butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells. (C) 2004 Elsevier Ltd. All rights reserved.