di-i-propyl 2-oxo-butandioate | 72816-63-8

• 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-butandioate
• 英文别名: isopropyl oxobutanedioate；Oxalessigsaeure-diisopropylester；Dipropan-2-yl 2-oxobutanedioate
• CAS: 72816-63-8
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: QDIADSKMUFZAHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-butandioate 在 baker's yeast 作用下， 生成 3-hydroxypropionic acid isopropyl ester 、 2S-Hydroxy-succinic diisopropyl ester
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(99)00286-4
• 作为产物：
  描述：

  Diisopropyl acetylenedicarboxylate 在 硫酸 作用下， 生成 di-i-propyl 2-oxo-butandioate
  参考文献：
  名称：

  Luebbe,F. et al., Liebigs Annalen der Chemie, 1979, p. 1696 - 1701

  摘要：

  DOI：

文献信息

• The First Complete Identification of a Diastereomeric Catalyst−Substrate (Alkoxide) Species in an Enantioselective Ketone Hydrogenation. Mechanistic Investigations
  作者：Christopher J. A. Daley、Steven H. Bergens

  DOI：10.1021/ja0102991

  日期：2002.4.1

  structures of the major diastereomer catalyst-alkoxide complexes (5, 8, and 10) were unambiguously determined by variable-temperature NMR spectroscopy. The major diastereomers (5, 8, and 10) had the same absolute configuration as the major product enantiomers from the catalytic hydrogenation of 2, 3, and 4 with 1 as catalyst. The ratio of major to minor alkoxide diastereomers was similar to the ee of

  二烷基 3,3-二甲基草酰乙酸酮底物（2、3 和 4；分别为烷基 = Me、(i)Pr 和 (t)Bu）的对映选择性氢化由 [Ru((R)-BINAP) 催化(H)(MeCN)(n)(sol)(3-n)](BF(4)) (1, n = 0-3, sol = THF 或 MeOH, (R)-BINAP = (R)-2 ,2'-双(二苯基膦基)-1,1'-联萘)在高达 82% ee (R) 中。活性催化剂 1 与 1 当量底物（2、3 或 4）在 THF 或 MeOH 溶液中的反应形成非对映异构催化剂-醇盐配合物 [Ru((R)-BINAP)(MeCN)(OCH(CO(2) R)-(C(CH(3))(2)CO(2)R))](BF(4)) (5/6 R = Me, 8/9 R = (i)Pr, 10 R = (t)Bu，分别）通过氢化物加成到酮羰基碳和钌加成到氧。主要非对映异构体 5、8、和 10)
• Bagrov, F. V.; Vasil'eva, T. V.; Bagrov, D. F., Russian Journal of General Chemistry, 1994, vol. 64, # 9.1, p. 1320 - 1323
  作者：Bagrov, F. V.、Vasil'eva, T. V.、Bagrov, D. F.

  DOI：——

  日期：——
• Bagrov, F. V.; Bagrov, D. F., Russian Journal of Organic Chemistry, 1993, vol. 29, # 11.2, p. 1876 - 1878
  作者：Bagrov, F. V.、Bagrov, D. F.

  DOI：——

  日期：——
• Bagrov, F. V., Russian Journal of Organic Chemistry, 1994, vol. 30, # 11, p. 1768 - 1770
  作者：Bagrov, F. V.

  DOI：——

  日期：——
• LUEBBE F.; SUCROW W.; RAU D., LIEBIGS ANN. CHEM., 1979, NO 11, 1696-1701
  作者：LUEBBE F.、 SUCROW W.、 RAU D.

  DOI：——

  日期：——