Ethyl α,β-dicyano-α-methylisovalerate | 95765-58-5

• 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 α,β-dicyano-α-methylisovalerate
• 英文别名: ethyl 2,3-dimethyl-2,3-dicyanobutyrate；2,3-dicyano-2,3-dimethyl-butyric acid ethyl ester；2,3-Dicyan-2,3-dimethyl-buttersaeure-aethylester；α.β-Dimethyl-α.β-dicyan-buttersaeure-aethylester；Ethyl 2,3-dicyano-2,3-dimethylbutanoate
• CAS: 95765-58-5
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: KQNIFTIOQURYDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl α,β-dicyano-α-methylisovalerate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 2,2,3-三甲基丁二酸
  参考文献：
  名称：

  Le Moal,H. et al., Bulletin de la Societe Chimique de France, 1964, p. 2553 - 2558

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-2-methyl-propionitrile 、 2-氰基丙酸乙酯 在 potassium tert-butylate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 23.0h， 以59%的产率得到Ethyl α,β-dicyano-α-methylisovalerate
  参考文献：
  名称：

  Alkylation of Nitrile Anions by Tertiary .alpha.-Halo Ketones and Nitriles

  摘要：

  Potassium salts of nitriles bearing carbethoxy, cyano, or phenyl groups at the alpha carbon [(RR'CCN)K:R' = CO(2)Et, CN, Ph] react with tertiary alpha-halo ketones and nitriles (1-5) in DMSO or HMPA to provide the alkylated beta-keto- or beta-cyano-beta,beta-dialkyl nitriles 6-10 in useful yields. (PhCHCN)(-) undergoes cyclization with p-XC(6)H(4)COCCl(CH3)(2) to produce 2(5H)-furanone 11. Reaction of (Ph(2)CCN)(-) with PhCOCCl(CH3)(2) affords the hydrolyzed ketone 12a and recovered carbon acid, while the anion undergoes oxidative dimerization to NCCPh(2)CPh(2)CN with p-O2NC6H4COCCl(CH3)(2) with concomitant formation of the reduced ketone p-O2NC6H4COCH(CH3)(2) and the hydrolyzed ketone 12b. The alkylations of [NCC(CH3)CO(2)Et](-) and [NCC(CH3)CN](-) with p-O(2)NC(6)H(4)COCX(CH3)(2) take place by the S(RN)1-process.

  DOI：

  10.1021/jo00122a018

文献信息

• Synthesis of Isoornithines and Methylputrescines. An Evaluation of Their Inhibitory Effects on Ornithine Decarboxylase
  作者：Gerardo Aizencang、Rosalia B. Frydman、Sergio Giorgieri、Luis Sambrotta、Liliana Guerra、Benjamin Frydman

  DOI：10.1021/jm00021a024

  日期：1995.10

  decarboxylated by liver ornithine decarboxylase (ODC, EC 4.1.1.17) of thioacetamide-treated rats but were good competitive inhibitors of the enzyme (Ki ranged from 0.72 to 1.79 mM). When assayed in vivo in the treated rats, the above mentioned isoornithines were also found to inhibit liver ODC when administered 1 h before sacrifice. When the methylputrescines formally derived from the decarboxylation

  2-（氨基甲基）-4-氨基丁酸（异鸟氨酸），3-甲基异鸟氨酸和2,3-二甲基异鸟氨酸不会被硫代乙酰胺治疗的大鼠的肝脏鸟氨酸脱羧酶（ODC，EC 4.1.1.17）脱羧，但它们是该药的良好竞争抑制剂酶（Ki介于0.72至1.79 mM之间）。当在治疗的大鼠体内进行测定时，还发现上述异鸟氨酸在处死前1小时给药时能抑制肝脏ODC。当在大鼠肝脏ODC上测定从几种异鸟氨酸的脱羧形式正式衍生而来的甲基氨基乙酸时，发现只有2,3-二甲基氨基氨基乙酸降低了酶活性。当在体内测定时，发现在给药后1小时测量ODC活性，ODC活性降低60％。给药4小时后恢复作用。H-35肝癌细胞不吸收异鸟氨酸。因此，它们不会影响其ODC活动。然而，2,3-二甲基腐胺被转运到细胞中并显着降低其ODC活性。
• Higson; Thorpe, Journal of the Chemical Society, 1906, vol. 89, p. 1460
  作者：Higson、Thorpe

  DOI：——

  日期：——
• Alkylation of Nitrile Anions by Tertiary .alpha.-Halo Ketones and Nitriles
  作者：Francisco Ros、Jose de la Rosa、Juan Enfedaque

  DOI：10.1021/jo00122a018

  日期：1995.9

  Potassium salts of nitriles bearing carbethoxy, cyano, or phenyl groups at the alpha carbon [(RR'CCN)K:R' = CO(2)Et, CN, Ph] react with tertiary alpha-halo ketones and nitriles (1-5) in DMSO or HMPA to provide the alkylated beta-keto- or beta-cyano-beta,beta-dialkyl nitriles 6-10 in useful yields. (PhCHCN)(-) undergoes cyclization with p-XC(6)H(4)COCCl(CH3)(2) to produce 2(5H)-furanone 11. Reaction of (Ph(2)CCN)(-) with PhCOCCl(CH3)(2) affords the hydrolyzed ketone 12a and recovered carbon acid, while the anion undergoes oxidative dimerization to NCCPh(2)CPh(2)CN with p-O2NC6H4COCCl(CH3)(2) with concomitant formation of the reduced ketone p-O2NC6H4COCH(CH3)(2) and the hydrolyzed ketone 12b. The alkylations of [NCC(CH3)CO(2)Et](-) and [NCC(CH3)CN](-) with p-O(2)NC(6)H(4)COCX(CH3)(2) take place by the S(RN)1-process.
• Le Moal,H. et al., Bulletin de la Societe Chimique de France, 1964, p. 2553 - 2558
  作者：Le Moal,H. et al.

  DOI：——

  日期：——