2-cyano-4,4-dimethyl-pent-2-enoic acid ethyl ester | 52685-34-4

• 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: 2-cyano-4,4-dimethyl-pent-2-enoic acid ethyl ester
• 英文别名: 2-Cyan-4,4-dimethyl-pent-2-ensaeure-aethylester；Ethyl 2-cyano-4,4-dimethylpent-2-enoate
• CAS: 52685-34-4
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: ATVJZKJIRNXTEK-UHFFFAOYSA-N

物化性质

• 沸点：
  259.0±23.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-4,4-dimethyl-pent-2-enoic acid ethyl ester 在 氢溴酸 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 3-tert-butylglutaric acid
  参考文献：
  名称：

  Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols

  摘要：

  The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated. Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtain the corresponding diesters 16-20. The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, with the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively. The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

  DOI：

  10.1021/jo00053a027
• 作为产物：
  描述：

  3,3-二甲基-1,2-丁二醇 在 乙酸铵 、 sodium periodate 、 硫酸 、 溶剂黄146 、 苯 作用下， 生成 2-cyano-4,4-dimethyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Braendstroem, Acta Chemica Scandinavica (1947), 1959, vol. 13, p. 608

  摘要：

  DOI：

文献信息

• Catalyst-free stereoselective cyclopropanation of electron deficient alkenes with ethyl diazoacetate
  作者：Ram Awatar Maurya、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Srikanth P. S.、D. Chandrasekhar、Ahmed Kamal

  DOI：10.1039/c3ra42374c

  日期：——

  activated electron deficient alkenes react with ethyl diazoacetate in a Michael Initiated Ring Closure (MIRC) fashion to yield highly diastereoselective cyclopropanes even without any added base or metal catalyst. Following the strategy, a one-pot, two-step, three-component reaction of aldehydes, malononitrile/ethyl cyanoacetate, and ethyl diazoacetate was successfully developed.

  双重活化的电子不足的烯烃与重氮乙酸乙酯以迈克尔引发的闭环（MIRC）方式反应，即使不添加任何碱或金属催化剂也可产生高度非对映选择性的环丙烷。遵循该策略，成功开发了醛，丙二腈/氰基乙酸乙酯和重氮乙酸乙酯的一锅，两步，三组分反应。
• Synergistic combination for treating herpes infections
  申请人：Bio-Mega, Inc.

  公开号：US05380727A1

  公开（公告）日：1995-01-10

  Disclosed herein is a combination of an antiviral nucleoside analog and a ribonucleotide reductase inhibiting peptide derivative. The combination is useful for treating herpes infections.

  本文揭示了一种抗病毒核苷类似物和核糖核酸还原酶抑制肽衍生物的组合物。该组合物可用于治疗疱疹感染。
• Antiherpes peptide derivatives having a 1,4-dioxo-C, N-terminus
  申请人：Bio-Mega/Boehringer Ingelheim Research Inc.

  公开号：US05484771A1

  公开（公告）日：1996-01-16

  Described herein are peptide derivatives of the formula R.sup.1 NH--CO--Q--C(O)--NR.sup.2 --CH[CH.sub.2 C(O)--Y]--C(O)--NH--CH[CR.sup.3 (R.sup.4)--COOH]--C(W)--NH--CHR.sup.5 --Z wherein R.sup.1 is an optionally substituted alkyl or optionally substituted phenylalkyl, R.sup.2 is hydrogen or alkyl, R.sup.3 and R.sup.4 each independently is hydrogen or alkyl, or R.sup.3 and R.sup.4 are joined to form a cycloalkyl. R.sup.5 is alkyl, cycloalkyl or (cycloalkyl)alkyl, Q is a divalent radical, for example, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or 1,2-cyclohexanediyl, which serves as a two carbon spacer. W is oxo or thioxo, Y is, for example, an alkoxy or a monosubstituted or disubsdtuted ammo, and Z is a terminal unit, for example, hydrogen, COOH or CH.sub.2 OH. The derivatives are useful for treating herpes infections.

  本文描述了公式R.sup.1 NH--CO--Q--C(O)--NR.sup.2 --CH[CH.sub.2 C(O)--Y]--C(O)--NH--CH[CR.sup.3 (R.sup.4)--COOH]--C(W)--NH--CHR.sup.5 --Z的肽衍生物。其中，R.sup.1是可选择取代的烷基或可选择取代的苯基烷基，R.sup.2是氢或烷基，R.sup.3和R.sup.4各自独立地是氢或烷基，或者R.sup.3和R.sup.4结合形成环烷基。R.sup.5是烷基、环烷基或(环烷基)烷基，Q是二价基团，例如，--CH.sub.2 CH.sub.2 --、--CH.dbd.CH--或1,2-环己基二基，用作两个碳的间隔。W是氧或硫氧，Y是例如烷氧基或单取代或双取代的氨基，Z是一个末端基元，例如氢、COOH或CH.sub.2 OH。这些衍生物对治疗疱疹感染有用。
• Steric effects in high pressure Knoevenagel reactions
  作者：Gérard Jenner

  DOI：10.1016/s0040-4039(00)01930-4

  日期：2001.1

  The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.
• The discovery of potent, orally bioavailable pyrimidine-5-carbonitrile-6-alkyl CXCR2 receptor antagonists
  作者：David W. Porter、Michelle Bradley、Zarin Brown、Steven J. Charlton、Brian Cox、Peter Hunt、Diana Janus、Sarah Lewis、Paul Oakley、Des O’Connor、John Reilly、Nichola Smith、Neil J. Press

  DOI：10.1016/j.bmcl.2014.06.011

  日期：2014.8

  A hit-to-lead optimisation programme was carried out on the Novartis archive screening hit, pyrimidine 2-((2,6-dichlorobenzyl)thio)-5-isocyano-6-phenylpyrimidin-4-ol 4, resulting in the discovery of CXCR2 receptor antagonist 24(2,3-difluorobenzyl)thio)-6-(2-(hydroxymethyl)cyclopropyl)-5-isocyanopyrimidin-4-ol 24. The SAR was investigated by systematic variation of the aromatic group at c-6, the linker between c-2 and the halogenated ring, and the c-5 nitrile moiety. (C) 2014 Elsevier Ltd. All rights reserved.