3-(2-methylallyloxy)-3-oxopropanoic acid | 1319767-12-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2-methylallyloxy)-3-oxopropanoic acid
• 英文别名: 3-(2-Methylprop-2-enoxy)-3-oxopropanoic acid
• CAS: 1319767-12-8
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: CJSUWAHSPUTEKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methylallyloxy)-3-oxopropanoic acid 在 potassium tert-butylate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 (±)-2-methylallyl 2-methyl-3-(methyl(phenyl)amino)-3-oxopropanoate
  参考文献：
  名称：

  DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids

  摘要：

  An efficient route to 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position has been developed via a DDQ-mediated Intramolecular-Dehydrogenative-Coupling (IDC). The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (7) concomitant with dehydrogenative-coupling in the presence of stoichiometric amount of DDQ. A tentative mechanistic route has been proposed for the oxidative coupling. The methodology provides a two-step entry to the ergoline structure of ergot alkaloids.

  DOI：

  10.1021/ol400899e
• 作为产物：
  描述：

  丙二酸 、 2-甲基-2-丙烯-1-醇 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以64%的产率得到3-(2-methylallyloxy)-3-oxopropanoic acid
  参考文献：
  名称：

  Asymmetric Decarboxylative Allylation of Oxindoles

  摘要：

  An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

  DOI：

  10.1021/ol201613a

文献信息

• Intramolecular Dehydrogenative Coupling of sp² C–H and sp³ C–H Bonds: An Expeditious Route to 2-Oxindoles
  作者：Santanu Ghosh、Subhadip De、Badrinath N. Kakde、Subhajit Bhunia、Amit Adhikary、Alakesh Bisai

  DOI：10.1021/ol302767w

  日期：2012.12.7

  An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of beta-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
• ARUTYUNYAN, O MI HAM V. S.;KOCHIKYAN, T. V.;MARKARYAN, T. YU.;AVETISYAN, +, ARM. XIM. ZH., 41,(1988) N 8, S. 522-524
  作者：ARUTYUNYAN, O MI HAM V. S.、KOCHIKYAN, T. V.、MARKARYAN, T. YU.、AVETISYAN, +

  DOI：——

  日期：——
• US5030715A
  申请人：——

  公开号：US5030715A

  公开（公告）日：1991-07-09
• US5296501A
  申请人：——

  公开号：US5296501A

  公开（公告）日：1994-03-22
• [EN] IMPROVED SYNTHESIS OF MACROCYCLIC TETRAAMIDO COMPOUNDS AND NEW METAL INSERTION PROCESS<br/>[FR] SYNTHESE AMELIOREE DE COMPOSES TETRAAMIDO-MACROCYCLIQUES ET NOUVEAU PROCEDE D'INSERTION D'UN METAL
  申请人：UNIV CARNEGIE MELLON

  公开号：WO2004076425A1

  公开（公告）日：2004-09-10

  An improved method of synthesizing a macrocyclic tetraamido compound includes protecting the amino portion of an amino carboxylic acid to form a protected amino carboxylic acid; exposing the protected amino carboxylic acid to a first solvent, preferably a hydrocarbon solvent, such as toluene or 1,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane. The carboxylic acid portion of the protected amino carboxylic acid is then converted to an activated carboxylic acid by one of esterification or acid halide formation, to form a protected amino activated carboxylic acid derivative. The protected amino activated carboxylic acid derivative is reacted with a diamine in the presence of a second solvent, such as THF or ,2-dichloroethane, dichloromethane, dibromomethane and 1,2-dibromoethane, to form a protected diamide diamine intermediate. Following deprotection, the diamide diamine intermediate is reacted with an activated diacid, such as an activated malonate, oxalate or succinate derivative to form the macrocyclic tetraamido compound. The macrocyclic tetraamido compound may further be complexed with a transition metal.