dimethyl 3-benzylglutarate | 91478-80-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl 3-benzylglutarate
• 英文别名: Dimethyl 3-benzylpentanedioate
• CAS: 91478-80-7
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: OUNRVENICJPJHH-UHFFFAOYSA-N

物化性质

• 沸点：
  341.3±35.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 3-benzylglutarate 生成 (S)-3-Benzyl-pentanedioic acid monomethyl ester
  参考文献：
  名称：

  Enzymes in organic synthesis. 35. Stereoselective pig liver esterase catalyzed hydrolyses of 3-substituted glutarate diesters. Optimization of enantiomeric excess via reaction conditions control

  摘要：

  DOI：

  10.1021/jo00361a021
• 作为产物：
  描述：

  苯乙醛 在 1.) base 作用下， 生成 dimethyl 3-benzylglutarate
  参考文献：
  名称：

  猪肝酯酶对3-烷基单取代戊二酸二烷基酯的对映选择性水解：结构-光学纯度关系

  摘要：

  用猪肝酯酶水解3-单取代的戊二酸二烷基酯，得到相应的手性半酯。从具有更疏水性质的前手性底物获得了更高光学纯度的合成上有用的半酯。

  DOI：

  10.1016/s0040-4039(00)80391-3

文献信息

• Preparation of chiral δ-lactones via enantiotopically specific pig liver esterase-catalysed hydrolyses of 3-substituted glutaric acid diesters
  作者：Christopher J. Francis、J. Bryan Jones

  DOI：10.1039/c39840000579

  日期：——

  Pig liver esterase-catalysed hydrolyses of 3-monosubstituted glutaric acid diesters are pro-S enantiotopically specific for a broad range of C-3 substituents and permit either enantiomer of the corresponding 3-substituted valerolac- tones of 100% e.e. to be readily prepared.

  的3-单取代的戊二酸的二酯猪肝酯酶催化的水解是亲- š enantiotopically特异于范围广泛的C-3取代基，并允许任一相应的3-取代的valerolac-音调100％容易地制备EE的对映体。
• Design, Synthesis, and Antipicornavirus Activity of 1-[5-(4-Arylphenoxy)alkyl]-3-pyridin-4-ylimidazolidin-2-one Derivatives
  作者：Chih-Shiang Chang、Ying-Ting Lin、Shin-Ru Shih、Chung-Chi Lee、Yen-Chun Lee、Chia-Liang Tai、Sung-Nien Tseng、Jyh-Haur Chern

  DOI：10.1021/jm050033v

  日期：2005.5.1

  A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.
• NAKADA, MASAHISA;KOBAYASHI, SUSUMU;OHNO, MASAJI, TETRAHEDRON LETT., 29,(1988) N 32, C. 3951-3954
  作者：NAKADA, MASAHISA、KOBAYASHI, SUSUMU、OHNO, MASAJI

  DOI：——

  日期：——
• Enantioselective hydrolysis of dialkyl 3-monosubstituted glutarates with pig liver esterase: Structure-optical purity relationships
  作者：Masahisa Nakada、Susumu Kobayashi、Masaji Ohno、Shigeo Iwasaki、Shigenobu Okuda

  DOI：10.1016/s0040-4039(00)80391-3

  日期：1988.1

  Dialkyl 3-monosubstituted glutarates are subjected to hydrolysis with pig liver esterase to afford the corresponding chiral half-esters. Synthetically useful half-esters of higher optical purity are obtained from the prochiral substrates of more hydrophobic nature.

  用猪肝酯酶水解3-单取代的戊二酸二烷基酯，得到相应的手性半酯。从具有更疏水性质的前手性底物获得了更高光学纯度的合成上有用的半酯。
• Enzymes in organic synthesis. 35. Stereoselective pig liver esterase catalyzed hydrolyses of 3-substituted glutarate diesters. Optimization of enantiomeric excess via reaction conditions control
  作者：Lister K. P. Lam、Raymond A. H. F. Hui、J. Bryan Jones

  DOI：10.1021/jo00361a021

  日期：1986.5