3-(呋喃-2-基)-3-氧代丙酸 | 70048-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(呋喃-2-基)-3-氧代丙酸
• 英文名称: 3-(furan-2-yl)-3-oxopropanoic acid
• 英文别名: 3-furan-2-yl-3-oxo-propionic acid
• CAS: 70048-96-3
• 化学式: C₇H₆O₄
• 分子量: 154.122
• InChiKey: KWRQUQONMCVOMB-UHFFFAOYSA-N

物化性质

• 沸点：
  357.8±22.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(呋喃-2-基)-3-氧代丙酸 在 碳酸氢钠 作用下， 生成 (6R)-7t-(3-furan-2-yl-3-oxo-propionylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  New cephalosporins with 7-acyl groups derived from .BETA.-ketoacids. I. 7-(.BETA.-Ketoacylamino)cephalosporins.

  摘要：

  本文介绍了一系列在 3 位上带有乙酰氧甲基或杂环硫甲基的 7-(β-酮酰氨基)头孢菌素 (1) 的合成和抗菌谱。在该系列中，3-[[(1-甲基-1H-四唑-5-基)硫]甲基]-7-(3-氧代丁酰基氨基)头孢-3-em-4-羧酸（11）在体外和体内试验中显示出中等抗菌活性。

  DOI：

  10.7164/antibiotics.31.1245

文献信息

• 3,4-Alkadienyl ketones via the palladium-catalyzed decarboxylative allenylation of 3-oxocarboxylic acids
  作者：Tonghao Zhu、Shengming Ma

  DOI：10.1039/c7cc02050c

  日期：——

  In this communication, we report a palladium-catalyzed decarboxylative allenylation of benzyl carbonates and tert-butyl carbonates of 2,3-allenols with 3-oxocarboxylic acids. The reaction provides a new and straightforward approach to 3,4-dienyl ketones under mild conditions.

  在此通讯中，我们报告了钯催化的3-氧代羧酸的2,3-烯丙基碳酸苄酯和碳酸叔丁基碳酸酯的脱羧烯丙基化。该反应在温和条件下为3,4-二烯基酮提供了一种新的直接方法。
• Decarboxylative Alkylation of<i>β</i>-Keto Acids with Isochromans under Oxidative Conditions
  作者：Yan Chen、Shi-Kai Tian

  DOI：10.1002/cjoc.201200994

  日期：2013.1

  An unprecedented decarboxylative alkylation reaction of β‐keto acids with isochromans has been developed under oxidative conditions. A range of β‐keto acids smoothly undergo decarboxylative alkylation with isochromans in the presence of 2,2,6,6‐tetramethylpiperdine‐1‐oxoammonium hexafluorophosphate to give structurally diverse 1‐acylmethylisochromans in moderate to excellent yields with extremely high

  在氧化条件下，β-酮酸与异色团发生了前所未有的脱羧烷基化反应。在2,2,6,6-四甲基哌啶-1-氧代铵六氟磷酸酯的存在下，一系列β-酮酸能顺利地与异色团进行脱羧烷基化反应，从而以适中至优异的产率提供结构多样的1-酰基甲基异色烷，并具有极高的区域选择性。
• Organocatalyzed Enantioselective Decarboxylative Mannich Reaction of β-Ketoacids with Pyrazolinone Ketimines for the Construction of Chiral β-Amino Ketone-Pyrazolinone Derivatives
  作者：Yang Zhou、Yong You、Zhen-Hua Wang、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1002/ejoc.201900346

  日期：2019.6.2

  An organocatalytic enantioselective decarboxylative Mannich reaction of pyrazolin‐5‐one derived ketimines with β‐ketoacids using quinine‐derived bifunctional squaramide as a catalyst has been developed. With the developed protocol, a series of chiral β‐amino ketone‐pyrazolinone derivatives were obtained in excellent yields (up to 99 %) with good enantioselectivities (up to 94:6 er).

  已开发出以奎宁为原料的双官能方丁二酰胺为催化剂，吡唑啉-5-酮衍生的酮亚胺与β-酮酸的有机催化对映选择性脱羧曼尼希反应。通过开发的方案，可以以优异的收率（高达99％）和良好的对映选择性（高达94：6 er）获得一系列手性β-氨基酮-吡唑啉酮衍生物。
• Cyclic Aldimines as Superior Electrophiles for Cu-Catalyzed Decarboxylative Mannich Reaction of β-Ketoacids with a Broad Scope and High Enantioselectivity
  作者：Heng-Xia Zhang、Jing Nie、Hua Cai、Jun-An Ma

  DOI：10.1021/ol500929d

  日期：2014.5.2

  enantioselective decarboxylative Mannich reaction of cyclic aldimines with β-ketoacids is described. The cyclic structure of these aldimines, in which the C═N bond is constrained in the Z geometry, appears to be important, allowing Mannich condensation to proceed in high yields with excellent enantioselectivities. A chiral chroman-4-amine was synthesized from the decarboxylative Mannich product in several

  描述了一种新型的铜催化的环亚胺与β-酮酸的对映选择性脱羧曼尼希反应。这些Aldimines的环状结构（其中C═N键受限于Z几何形状）似乎很重要，这使得Mannich缩合反应能够以高收率和出色的对映选择性进行。在不损失对映选择性的情况下，由脱羧曼尼希产物经几个步骤合成了手性苯并吡喃-4-胺。
• Organocatalytic Asymmetric Decarboxylative Mannich Reaction of β-Keto Acids with Cyclic α-Ketiminophosphonates: Access to Quaternary α-Aminophosphonates
  作者：Yong-Jie Liu、Jin-Shan Li、Jing Nie、Jun-An Ma

  DOI：10.1021/acs.orglett.8b01422

  日期：2018.6.15

  An organocatalytic asymmetric decarboxylative Mannich reaction of β-keto acids with cyclic α-ketiminophosphonates has been developed. By using saccharide-derived bifunctional amine-thiourea catalysts bearing an axial chiral binaphthyl scaffold, a wide range of quaternary α-amino-γ-oxophosphonates were obtained in up to 93% yield and >99% ee. Furthermore, two interesting α-aminophosphonate derivatives

  已经开发了β-酮酸与环状α-酮亚氨基膦酸酯的有机催化不对称脱羧曼尼希反应。通过使用带有轴向手性双萘基骨架的衍生自糖的双功能胺-硫脲催化剂，可以以高达93％的收率和> 99％ee的产率获得各种范围的季α-氨基-γ-氧代膦酸酯。此外，通过简单的转化，从相应的脱羧曼尼希产物中合成了两种有趣的α-氨基膦酸酯衍生物。