allyl 3-allyloxycarbonyl-2-oxo-4-phenylbutanoate | 125582-89-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: allyl 3-allyloxycarbonyl-2-oxo-4-phenylbutanoate
• 英文别名: diallyl α-oxalhydrocinnamate；Butanedioic acid, oxo(phenylmethyl)-, di-2-propenyl ester；bis(prop-2-enyl) 2-benzyl-3-oxobutanedioate
• CAS: 125582-89-0
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: GCMJPYGDOIPINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl 3-allyloxycarbonyl-2-oxo-4-phenylbutanoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 甲酸 、 sodium hydride 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 3-fluoro-2-oxo-4-phenylbutanoic acid
  参考文献：
  名称：

  Synthesis of α-fluoroketones based on palladium-catalyzed Decar☐ylation reactions of allyl β-keto car☐ylates

  摘要：

  Fluorination of allyl beta-keto carboxylates using N-fluoro-2,4,6-pyridinium triflate gave allyl a-fluoro-a-keto carboxylates. Reaction of allyl alpha-fluoro-beta-keto carboxylates with formic acid in the presence of palladium-phosphine catalyst gave alpha-fluoro ketones. When the palladium-catalyzed reaction was carried out without formic acid, the decarboxylation-allylation took place to give alpha-fluoro-allylketones. Decarboxylation-dehydrogenation to afford alpha-fluoro-alpha,beta-unsaturated ketones was carried out with palladium catalysts in acetonitrile.

  DOI：

  10.1016/s0040-4020(01)80770-5
• 作为产物：
  描述：

  草酸烯丙酯 、 烯丙基3-苯基丙酸酯 在 sodium hydride 、 烯丙醇 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以73%的产率得到allyl 3-allyloxycarbonyl-2-oxo-4-phenylbutanoate
  参考文献：
  名称：

  钌催化的甲酸和三乙胺对烯丙基酯的还原裂解。在α-羟基酸短步合成中的应用

  摘要：

  探索了钌催化的烯丙基羧酸盐和碳酸盐与甲酸和三乙胺的还原裂解反应，得到烯烃。作为钌催化方法的一种应用，已经发现了一种合成α-羟基酸的新途径。烯丙基酯的还原裂解被认为是通过π-烯丙基钌中间体进行的。

  DOI：

  10.1016/0022-328x(94)80126-6

文献信息

• Facile Synthesis of α-Hydroxycarboxylic Acids by Ruthenium-Catalyzed Reduction of Diallyl α-Oxalylcarboxylates with Formic Acid
  作者：Isao Shimizu、Masafumi Tekawa、Yooichiroh Maruyama、Akio Yamamoto

  DOI：10.1246/cl.1992.1365

  日期：1992.7

  Reaction of diallyl α-oxalylcarboxylates with catalytic amounts of ruthenium complexes gave α-hydroxycarboxylic acids in good yields.

  使用少量钌络合物催化剂，二烯丙基α-草酰基羧酸盐反应生成α-羟基羧酸，收率良好。
• Facile Synthesis of α-Hydroxybutenolides and α-Keto-β-allyl-γ-butyrolactones
  作者：Isao Shimizu、Takashi Maruyama、Hajime Hasegawa

  DOI：10.1246/cl.1991.1349

  日期：1991.8

  carbonyl-γ-butyrolactones with ammonium formate in the presence of palladium catalyst gave α-hydroxybutenolides in good yields. When the reaction was carried out without ammonium formate, decarboxylation-allylation took place to give allyl enol ethers of α-hydroxybutenolides, which were converted to α-keto-β-allyl-γ-butyrolactones by the thermal Claisen rearrangement.

  在钯催化剂存在下，α-酮基-β-烷基-β-烯丙氧基羰基-γ-丁内酯与甲酸铵反应以良好的收率得到α-羟基丁烯内酯。当反应在没有甲酸铵的情况下进行时，发生脱羧-烯丙基化，得到 α-羟基丁烯内酯的烯丙醇醚，通过热克莱森重排将其转化为 α-酮基-β-烯丙基-γ-丁内酯。
• Shimizu, Isao; Makuta, Toshiyuki; Oshima, Masato, Chemistry Letters, 1989, p. 1457 - 1460
  作者：Shimizu, Isao、Makuta, Toshiyuki、Oshima, Masato

  DOI：——

  日期：——
• SHIMIZU, ISAO;MAKUTA, TOSHIYUKI;OSHIMA, MASATO, CHEM. LETT.,(1989) N, C. 1457-1460
  作者：SHIMIZU, ISAO、MAKUTA, TOSHIYUKI、OSHIMA, MASATO

  DOI：——

  日期：——
• Ruthenium-catalysed reductive cleavage of allylic esters with formic acid and triethylamine. Application to short-step synthesis of α-hydroxy acids
  作者：Yooichiroh Maruyama、Takao Sezaki、Masafumi Tekawa、Toshiaki Sakamoto、Isao Shimizu、Akio Yamamoto

  DOI：10.1016/0022-328x(94)80126-6

  日期：1994.6

  Ruthenium-catalysed reductive cleavage reactions of allylic carboxylates and carbonates with formic acid and triethylamine to give olefins were explored. As an application of the ruthenium-catalysed processes, a new synthetic route to α-hydroxy acids has been discovered. The reductive cleavage of allylic esters is considered to proceed through π-allylruthenium intermediates.

  探索了钌催化的烯丙基羧酸盐和碳酸盐与甲酸和三乙胺的还原裂解反应，得到烯烃。作为钌催化方法的一种应用，已经发现了一种合成α-羟基酸的新途径。烯丙基酯的还原裂解被认为是通过π-烯丙基钌中间体进行的。