2-氰基-5-氧代-2-苯基己酸乙酯 | 58623-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-氰基-5-氧代-2-苯基己酸乙酯
• 英文名称: ethyl 2-cyano-5-oxo-2-phenylhexanoate
• 英文别名: 2-cyano-5-oxo-2-phenyl-hexanoic acid ethyl ester；(+/-)-(3-Oxo-butyl)-phenyl-malonsaeure-aethylester-nitril；2-Cyan-5-oxo-2-phenyl-hexansaeure-aethylester
• CAS: 58623-78-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: KNODAWHPKGLFFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氰基-5-氧代-2-苯基己酸乙酯 在 盐酸 、 硫酸 、 溶剂黄146 作用下， 生成 2-methyl-5-phenyl-pentane-1,2,5-tricarboxylic acid
  参考文献：
  名称：

  The Mo−OH proton of the low-pH form of sulfite oxidase: Comparison of the hyperfine interactions obtained from pulsed ENDOR, CW-EPR and ESEEM measurements

  摘要：

  Pulsed electron nuclear double resonance (ENDOR) spectra have been obtained for the exchangeable Mo-OH proton of the low-pH form of native chicken liver sulfite oxidase (SO) and recombinant human SO for the first time. The spectra of the two enzymes are very similar, indicating a similar binding geometry of the hydroxyl ligand to the Mo center. The isotropic hyperfine interaction (hfi) constant for the proton of the OH ligand in both enzymes is about 26 MHz. The anisotropic components of the hfi obtained from the pulsed ENDOR spectra are about 1.6-1.8 times larger than those obtained by continuous-wave electron paramagnetic resonance and electron spin echo envelope modulation. These hfi differences are explained by a rotational disorder of the Mo-OH group. A similar rotational disorder of the coordinated exchangeable ligand has been found previously for the high-pH and phosphate-inhibited forms of SO.

  DOI：

  10.1007/bf03166122
• 作为产物：
  描述：

  丁烯酮 、 苯基氰基乙酸乙酯 在 N,N-二异丙基乙胺 作用下， 反应 1.33h， 以76%的产率得到2-氰基-5-氧代-2-苯基己酸乙酯
  参考文献：
  名称：

  迈克尔加成反应的对映选择性双金属催化形成四元立体中心。

  摘要：

  DOI：

  10.1002/anie.200803539

文献信息

• Enantioselective Michael Addition of α-Substituted Cyanoacetates to Vinyl Ketones Catalyzed by Bifunctional Organocatalysts
  作者：Tian-Yu Liu、Rui Li、Qian Chai、Jun Long、Bang-Jing Li、Yong Wu、Li-Sheng Ding、Ying-Chun Chen

  DOI：10.1002/chem.200600796

  日期：2007.1

  A highly enantioselective Michael addition of alpha-substituted cyanoacetates to vinyl ketones was accomplished in the presence of simple bifunctional thiourea/tertiary amine organocatalysts. A number of alpha-aryl or alkyl cyanoacetates have been successfully applied to give multifunctional compounds with an all-carbon-substituted quaternary stereocenter in excellent enantioselectivities (82-97 %

  在简单的双官能硫脲/叔胺有机催化剂的存在下，完成了α-取代的氰基乙酸酯向乙烯基酮的高度对映选择性迈克尔加成反应。许多α-芳基或氰基乙酸烷基酯已成功应用于具有全碳取代的季立构中心的多功能化合物，具有出色的对映选择性（82-97％ee）和收率（61-99％）。光学纯加合物可以平稳地转化为各种结构的β（2,2）-氨基酸酯。此外，基于加合物的绝对构型和计算研究，提出了一种有趣的反应模型，该模型涉及硫脲/叔胺催化剂和反应物之间的多个氢键相互作用。
• Henecka, Chemische Berichte, 1949, vol. 82, p. 104,110
  作者：Henecka

  DOI：——

  日期：——
• 162. Studies in the Sterol–Oestrone Group. Part II. Derivatives of 2-phenylcyclohexanone
  作者：J. C. Bardhan

  DOI：10.1039/jr9400000848

  日期：——