2,2,3-trimethyl-3-butensaeure-aethylester | 35293-39-1

• 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: 2,2,3-trimethyl-3-butensaeure-aethylester
• 英文别名: ethyl 2,2,3-trimethyl-3-butenoate；2,2,3-trimethyl-but-3-enoic acid ethyl ester；2,2,3-Trimethyl-but-3-ensaeure-aethylester；2.2.3-Trimethyl-3-butensaeure-ethylester；Ethyl 2,2,3-trimethylbut-3-enoate
• CAS: 35293-39-1
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: NBJSETUPMRLOLX-UHFFFAOYSA-N

物化性质

• 沸点：
  162 °C
• 密度：
  0.906 g/cm3(Temp: 12 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,3-trimethyl-3-butensaeure-aethylester 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,2,3-三甲基-3-丁烯酸
  参考文献：
  名称：

  使用异羟肟酸对烯烃进行无金属氧化

  摘要：

  描述了一种自由基介导的无金属烯烃氧胺化方法。该方法利用烯烃加成中脒氧基自由基的独特反应性，使用简单的偶氮二甲酸二异丙酯 (DIAD) 作为自由基陷阱提供一般的双官能化。该协议利用该过程的分子内性质，在所有情况下提供单一区域异构体。环状烯烃的双官能化提供了使用当前方法无法获得的具有高立体选择性的反式氧胺化产物，补充了顺式选择性氧胺化过程。

  DOI：

  10.1021/ja204255e
• 作为产物：
  描述：

  3-hydroxy-2,2,3-trimethyl-butyric acid ethyl ester 在 碘 作用下， 生成 2,2,3-trimethyl-3-butensaeure-aethylester
  参考文献：
  名称：

  Colonge; Dumont, Bulletin de la Societe Chimique de France, 1947, p. 43

  摘要：

  DOI：

文献信息

• Die Acylierung von Acetylenen mit ?, ?-unges�ttigten S�urechloriden. Eine neue Synthese von 5-Cyclopentenonen
  作者：Martin Karpf

  DOI：10.1002/hlca.19840670110

  日期：1984.2.1

  The Acylation of Acetylenes with β,γ-Unsaturated Acid Chlorides, A New Synthesis of 5-Substituted 2-Cyclopentenones

  β，γ-不饱和酰氯酰化乙炔，5-取代的2-环戊烯酮的新合成
• 1,2-Migrations in free radicals related to coenzyme B12-dependent rearrangements
  作者：Susan. Wollowitz、Jack. Halpern

  DOI：10.1021/ja00218a020

  日期：1988.5

  Les radicaux libres XC(CH 3 )(COOR)CH 2 • , ou X=C(=0)Me, C(=O)SEt, C(=0)OEt, C(=CH 2 )Me, et C 6 H 5 , sont generes par reaction des bromures correspondants avec (n-bu) 3 SnH. Etude de la reaction de migration-1,2 de X pour former les radicaux • C(CH 3 )(COOR)(CH 2 X)

  Les radicaux libres XC(CH 3 )(COOR)CH 2 • , ou X=C(=0)Me, C(=O)SEt, C(=0)OEt, C(=CH 2 )Me, et C 6 H 5 ，sont generes par reaction des bromures对应物avec (n-bu) 3 SnH。Etude de la reaction de migration-1,2 de X pour form les radicaux • C(CH 3 )(COOR)(CH 2 X)
• Blaise; Courtot, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1905, vol. 141, p. 725
  作者：Blaise、Courtot

  DOI：——

  日期：——
• A radical clock investigation of microsomal cytochrome P-450 hydroxylation of hydrocarbons. Rate of oxygen rebound
  作者：Vincent W. Bowry、K. U. Ingold

  DOI：10.1021/ja00015a025

  日期：1991.7

  A number of alkyl-substituted cyclopropanes for which the rates of ring opening of the corresponding cyclopropylcarbinyl radicals have been determined (see preceding paper in this issue) have been used as substrates for hydroxylation by phenobarbital-induced, rat liver microsomal cytochrome P-450 at 37-degrees-C. Three of these compounds gave both ring-closed and ring-opened alcohols, thus allowing the rate constant, k(OH), for ''oxygen rebound'' onto the corresponding carbon-centered radicals to be determined. In particular, both trans- (1bH) and cis- (1cH) 1,2-dimethylcyclopropane gave 4-penten-2-ol (2bOH) and 2-methyl-3-buten-1-ol (3bOH) together with the corresponding trans- (1bOH) or cis-(1cOH) 2-methylcyclopropanemethanols. Of much greater importance, for both 1bH and 1cH the ratios of the yields of the secondary-to-primary ring-opened alcohols, i.e., [2bOH]/[3bOH], were the same, within experimental error as the ratio of the rates of ring opening of the corresponding trans- (1b.) and cis- (1c.) methylcyclopropylmethyl radicals in solution at 37-degrees-C. This indicates that when lb. and lc. are formed from their parent hydrocarbons by H-atom abstraction in the hydrophobic pocket of cytochrome P-450 they are not detectably constrained in their subsequent reactions by their unusual environment. From the ratio of the yields of the unrearranged alcohol to each of the rearranged alcohols we calculate k(OH) values of 1.5 and 1.6 x 10(10) s-1 for lbH as substrate and values of 1.9 and 1.8 x 10(10) s-1 for 1cH as substrate. Consistent with these values we have obtained k(OH) = 2.2 x 10(10) s-1 for bicyclo[2.1.0]pentane as substrate. Substrates such as methylcyclopropane and 1,1-dimethylcyclopropane, for which the corresponding cyclopropylmethyl radicals undergo relatively slow ring opening, yielded only the ring-closed alcohols on oxidation with cytochrome P-450. 1,1,2,2-Tetramethylcyclopropane gave only a trace of a ring-opened alcohol, corresponding to k(OH) = 2.5 x 10(11) s-1 for this substrate. Hexamethylcyclopropane gave no detectable ring-opened alcohol from which observation a limit for k(OH) > 5 X 10(11) s-1 can bc calculated. Possible explanations for the unexpected behavior of these last two, relatively bulky, substrates are discussed.
• Exclusive γ-coupling in the aldol reaction of α,β-unsaturated esters
  作者：Akira Kajikawa、Masuo Morisaki、Nobuo Ikekawa

  DOI：10.1016/s0040-4039(00)91194-8

  日期：1975.1