ethyl 2-{N,N-Diethylcarbamoyl)-2-ethylbutyrate | 134448-40-1

• 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: ethyl 2-{N,N-Diethylcarbamoyl)-2-ethylbutyrate
• 英文别名: ethyl 2-(diethylcarbamoyl)-2-ethylbutanoate；2,2,N,N-tetraethyl-malonamic acid ethyl ester；2,2,N,N-Tetraaethyl-malonamidsaeure-aethylester；Diaethylmalonsaeure-aethylester-diaethylamid；ethyl 2-(N,N-diethylcarbamoyl)-2-ethylbutyrate
• CAS: 134448-40-1
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: YFVBKDRYNNREQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-{N,N-Diethylcarbamoyl)-2-ethylbutyrate 、 乙酸酐 、 水 、 氯仿 在 ice 、 氯仿 、 水 、 magnesium sulfate 、 盐酸 、 乙醚 、 甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 26.72h， 以to yield 11 g (35%) of 3-diethylamino-2,2-diethylpropanol的产率得到3-diethylamino-2,2-diethylpropanol
  参考文献：
  名称：

  Use of 5-phenyl-2-furan esters, amides and ketones as neuroprotective

  摘要：

  本发明涵盖了使用5-苯基-2-呋喃酯，酰胺和酮及其组合物的方法，以防止或限制人类或低等动物中的神经元死亡或退化。这些方法包括向这样的人类或其他动物系统地给予化合物的安全有效量，该化合物的结构式为：##STR1## 其中（1）X为卤素或氢，Y为从未取代或卤素取代的甲基，卤素，硝基，氨基和甲氧基中选择的取代基；（2）R为R.sup.1 C（0）OH，R.sup.1 C（0）N（R.sup.3）.sub.2，N（R.sup.3）.sub.2，OR.sup.1 N（R.sup.3）.sub.2，R.sup.1 N（R.sup.3）.sub.2，N（R.sup.2）R.sup.1 N（R.sup.3）.sub.2或N（R.sup.2）N（R.sup.3）.sub.2；其中R.sup.1为未取代或取代为C.sub.1-C.sub.2烷基的C.sub.1-C.sub.3烷基；R.sup.2为氢或较低烷基；每个R.sup.3独立地为氢或较低烷基；或两个R.sup.3基团连接形成含有1或2个氧和氮中选择的杂原子的饱和的5-或6-成员杂环，所述杂环未取代或取代为较低烷基或羟基取代的较低烷基；或其药学上可接受的盐。

  公开号：

  US05214042A1
• 作为产物：
  描述：

  Diethyl-malonsaeure-monoethylester 在 氯化亚砜 、 苯 作用下， 生成 ethyl 2-{N,N-Diethylcarbamoyl)-2-ethylbutyrate
  参考文献：
  名称：

  Dumesnil, Bulletin de la Societe Chimique de France, 1922, vol. <4> 31, p. 689

  摘要：

  DOI：

文献信息

• Substrate-Directable Electron Transfer Reactions. Dramatic Rate Enhancement in the Chemoselective Reduction of Cyclic Esters Using SmI₂–H₂O: Mechanism, Scope, and Synthetic Utility
  作者：Michal Szostak、Malcolm Spain、Kimberly A. Choquette、Robert A. Flowers、David J. Procter

  DOI：10.1021/ja4078864

  日期：2013.10.23

  showing dramatic rate acceleration in the Sm(II)-mediated reduction of cyclic esters that is enabled by transient chelation between a directing group and the lanthanide center. This process allows unprecedented chemoselectivity in the reduction of cyclic esters using SmI2-H2O and for the first time proceeds with a broad substrate scope. Initial studies on the origin of selectivity and synthetic application

  底物导向反应在有机合成中起着关键作用，但在通过自由基机制进行的反应中并不常见。在此，我们提供了实验证据，表明 Sm(II) 介导的环酯还原速率显着加速，这是通过导向基团和镧系元素中心之间的瞬时螯合实现的。该过程在使用 SmI2-H2O 还原环酯时具有前所未有的化学选择性，并且首次在广泛的底物范围内进行。还公开了对形成碳-碳键的选择性起源和合成应用的初步研究。
• Use of 5-phenyl-2-furan esters, amides and ketones as neuroprotective
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：US05214042A1

  公开（公告）日：1993-05-25

  The present invention encompasses methods of using 5-phenyl-2-furan esters, amides and ketones and compositions thereof to prevent or limit neuronal death or degeneration in a human or lower animal. These methods comprise systemically administering to such human or other animal a safe and effective amount of a compound of the formula: ##STR1## wherein (1) X is halo or hydrogen, and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (2) R is R.sup.1 C(0)OH, R.sup.1 C(0)N(R.sup.3).sub.2, N(R.sup.3).sub.2, OR.sup.1 N(R.sup.3).sub.2, R.sup.1 N(R.sup.3).sub.2, N(R.sup.2)R.sup.1 N(R.sup.3).sub.2, or N(R.sup.2)N(R.sup.3).sub.2 ; where R.sup.1 is C.sub.1 -C.sub.3 alkyl which is unsubstituted or substituted with C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or lower alkyl; and each R.sup.3 is, independently, hydrogen or lower alkyl; or both R.sup.3 groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen, and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically acceptable salt thereof.

  本发明涵盖了使用5-苯基-2-呋喃酯，酰胺和酮及其组合物的方法，以防止或限制人类或低等动物中的神经元死亡或退化。这些方法包括向这样的人类或其他动物系统地给予化合物的安全有效量，该化合物的结构式为：##STR1## 其中（1）X为卤素或氢，Y为从未取代或卤素取代的甲基，卤素，硝基，氨基和甲氧基中选择的取代基；（2）R为R.sup.1 C（0）OH，R.sup.1 C（0）N（R.sup.3）.sub.2，N（R.sup.3）.sub.2，OR.sup.1 N（R.sup.3）.sub.2，R.sup.1 N（R.sup.3）.sub.2，N（R.sup.2）R.sup.1 N（R.sup.3）.sub.2或N（R.sup.2）N（R.sup.3）.sub.2；其中R.sup.1为未取代或取代为C.sub.1-C.sub.2烷基的C.sub.1-C.sub.3烷基；R.sup.2为氢或较低烷基；每个R.sup.3独立地为氢或较低烷基；或两个R.sup.3基团连接形成含有1或2个氧和氮中选择的杂原子的饱和的5-或6-成员杂环，所述杂环未取代或取代为较低烷基或羟基取代的较低烷基；或其药学上可接受的盐。
• Use of 5-phenyl-2-furan esters and amides as antiepileptic agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：US05023272A1

  公开（公告）日：1991-06-11

  A method of preventing epileptic seizures in a human or mammal subject susceptible to said seizures, comprising systemically administering to said subject a safe and effective amount of a compound of the formula: ##STR1## wherein (a) X is halo or hydrogen, and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (b) R is N(R.sup.3).sub.2, OR.sup.1 N(R.sup.3).sub.2, N(R.sup.2)R.sup.1 N(R.sup.3).sub.2, or N(R.sup.2)N(R.sup.3).sub.2 ; where R.sup.1 is C.sub.1 -C.sub.3 alkylene which is unsubstituted or substituted with C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or lower alkyl; and each R.sup.3 is, independently, hydrogen or lower alkyl; or both R.sup.3 groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically-acceptable salt thereof. Preferably X is halo, preferably Y is trifluoromethyl, and R is preferably 3-diethylamino-2,2-dimethylpropoxy.

  一种预防易患癫痫发作的人或哺乳动物主体的方法，包括向该主体系统地给予化合物的安全有效剂量，所述化合物的式为：##STR1## 其中（a）X为卤素或氢，Y为从未取代或卤素取代的甲基，卤素，硝基，氨基和甲氧基中选择的取代基；（b）R为N（R.sup.3）.sub.2，OR.sup.1 N（R.sup.3）.sub.2，N（R.sup.2）R.sup.1 N（R.sup.3）.sub.2或N（R.sup.2）N（R.sup.3）.sub.2；其中R.sup.1为未取代或取代为C.sub.1-C.sub.2烷基的C.sub.1-C.sub.3烷基；R.sup.2为氢或较低的烷基；每个R.sup.3独立地为氢或较低的烷基；或两个R.sup.3基团连接形成饱和的5-或6-成员杂环，其中包含从氧和氮中选择的1或2个杂原子，所述杂环未取代或取代为较低的烷基或羟基取代的较低的烷基；或其药学上可接受的盐。优选X为卤素，优选Y为三氟甲基，R优选为3-二乙氨基-2,2-二甲基丙氧基。
• The use of 5-phenyl-2 furan esters and amides as antiepileptic agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0404231A1

  公开（公告）日：1990-12-27

  A method of preventing epileptic seizures in a human or lower animal subject susceptible to said seizures, comprising systemically administering to said subject a safe and effective amount of a compound of the formula: wherein (a) X is halo or nil, and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (b) R is N(R³)₂, OR¹N(R³)₂, N(R²)R¹N(R³)₂, or N(R²)N(R³)₂; where R¹ is C₁-C₃ alkyl which is unsubstituted or substituted with C₁-C₂ alkyl; R² is hydrogen or lower alkyl; and each R³ is, independently, hydrogen or lower alkyl, or both R³ groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically-acceptable salt thereof. Preferably X is halo, preferably Y is trifluoromethyl, and R is preferably 3-diethylamino-2,2-dimethylpropoxy.

  一种预防易受所述癫痫发作影响的人类或低等动物的癫痫发作的方法，包括向所述受试者全身施用安全有效量的式化合物： 其中 (a) X 是卤代或无，Y 是选自由未取代或卤代甲基、卤代、硝基、氨基和甲氧基组成的组的取代基；和 (b) R 是 N(R³)₂、OR¹N(R³)₂、N(R²)R¹N(R³)₂ 或 N(R²)N(R³)₂； 其中 R¹ 是未取代或被 C₁-C₂ 烷基取代的 C₁-C₃ 烷基； R² 是氢或低级烷基；以及 每个 R³ 独立地为氢或低级烷基，或两个 R³ 基团连接形成饱和的 5 或 6 元杂环，该杂环含有 1 或 2 个选自氧和氮的杂原子，且所述杂环未被取代或被低级烷基或羟基取代的低级烷基取代； 或其药学上可接受的盐。 X最好是卤代，Y最好是三氟甲基，R最好是3-二乙氨基-2,2-二甲基丙氧基。
• Novel use of 5-phenyl-2-furan esters, amides and ketones as neuroprotective agents
  申请人：Norwich Eaton Pharmaceuticals, Inc.

  公开号：EP0404233A2

  公开（公告）日：1990-12-27

  The present invention encompasses methods of using 5-phenyl-­2-furan esters, amides and ketones and compositions thereof to prevent or limit neuronal death or degeneration in a human or lower animal. These methods comprise systemically administering to such human or other animal a safe and effective amount of a compound of the formula: wherein (1) X is halo or nil; and Y is a substituent selected from the group consisting of unsubstituted or halogen-substituted methyl, halo, nitro, amino, and methoxy; and (2) R is R¹C(O)OH, R¹C(O)N(R³)₂, N(R³)₂, OR¹N(R³)₂, R¹N(R³)₂, N(R²)R¹N(R³)₂, or N(R²)N(R³)₂; where R¹ is C₁-C₃ alkyl which is unsubstituted or substituted with C₁-C₂ alkyl; R² is hydrogen or lower alkyl; and each R³ is, independently, hydrogen or lower alkyl; or both R³ groups are connected to form a saturated 5- or 6-membered heterocycle containing 1 or 2 heteroatoms selected from oxygen and nitrogen, and said heterocycle is unsubstituted or substituted with lower alkyl or hydroxy-substituted lower alkyl; or a pharmaceutically acceptable salt thereof.

  本发明包括使用 5-苯基-2-呋喃酯、酰胺和酮及其组合物防止或限制人或低等动物神经元死亡或变性的方法。这些方法包括向人或其他动物全身施用安全有效量的式化合物： 式中 (1) X 是卤代或零；Y 是选自由未取代或卤代甲基、卤代、硝基、氨基和甲氧基组成的组的取代基；和 (2) R 是 R¹C(O)OH、R¹C(O)N(R³)₂、N(R³)₂、OR¹N(R³)₂、R¹N(R³)₂、N(R²)R¹N(R³)₂ 或 N(R²)N(R³)₂；其中 R¹ 是未取代或被 C₁-C₂ 烷基取代的 C₁-C₃ 烷基； R² 是氢或低级烷基；以及 每个 R³ 独立地为氢或低级烷基；或两个 R³ 基团连接形成饱和的 5 或 6 元杂环，该杂环含有 1 或 2 个选自氧和氮的杂原子，且所述杂环未被取代或被低级烷基或羟基取代的低级烷基取代； 或其药学上可接受的盐。