3-oxo-3-(3,4,5-trimethoxyphenyl)propionic acid | 114195-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxo-3-(3,4,5-trimethoxyphenyl)propionic acid
• 英文别名: 3-oxo-3-(3,4,5-trimethoxyphenyl)propanoic acid
• CAS: 114195-15-2
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: HPWVUFYLAHNXQK-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±45.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-oxo-3-(3,4,5-trimethoxyphenyl)propionic acid 在 氢氧化钾 、 phosphate buffer 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 6-(3-Benzyloxy-4-methoxy-phenyl)-7-(3,4,5-trimethoxy-phenyl)-2,3,8,8a-tetrahydro-1H-indolizin-5-one
  参考文献：
  名称：

  Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents

  摘要：

  A series of 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues were synthesized and evaluated for cytotoxic activity against eight human cancer cell lines. Compounds 18, 21, 28, 29, 30 and 31 showed cytotoxic activity with GI(50) values in the range of 2.1-8.1 muM concentration. Among these, compounds 21 and 28 exhibited good pharmacokinetic properties. These compounds were further evaluated for their in vivo efficacy in modified hollow fibre assay (HFA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00263-4
• 作为产物：
  描述：

  3-氧代-3-(3,4,5-三甲氧基苯基)丙酸甲酯 在 氢氧化钾 作用下， 反应 24.0h， 生成 3-oxo-3-(3,4,5-trimethoxyphenyl)propionic acid
  参考文献：
  名称：

  Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents

  摘要：

  A series of 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues were synthesized and evaluated for cytotoxic activity against eight human cancer cell lines. Compounds 18, 21, 28, 29, 30 and 31 showed cytotoxic activity with GI(50) values in the range of 2.1-8.1 muM concentration. Among these, compounds 21 and 28 exhibited good pharmacokinetic properties. These compounds were further evaluated for their in vivo efficacy in modified hollow fibre assay (HFA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00263-4

文献信息

• Substrate‐Induced Dimerization Assembly of Chiral Macrocycle Catalysts toward Cooperative Asymmetric Catalysis
  作者：Hao Guo、Lie‐Wei Zhang、Hao Zhou、Wei Meng、Yu‐Fei Ao、De‐Xian Wang、Qi‐Qiang Wang

  DOI：10.1002/anie.201910399

  日期：2020.2.10

  catalyze the decarboxylative Mannich reaction of cyclic aldimines containing a sulfamate heading group. The imine substrate can be activated toward nucleophilic attack of β-ketoacid by a cooperative hydrogen-bonding network enabled by sulfamate-induced dimerization assembly of the macrocycle catalysts. Highly efficient (>95 % yield in most cases) and enantioselective (up to 97.5:2.5 er) transformation

  人工诱导的手性大环催化剂二聚体组装的人工系统能够实现高度协作的氢键活化网络，以实现有效的对映选择性转化。这些大环含有两个硫脲和两个手性二胺部分，并与硫酸盐二聚形成三明治状的组装体。然后，大环采用扩展的构象并相互补充氢键相互作用位点。受客体诱导的动态组装的启发，这些大环催化含有氨基磺酸根的环状亚胺的脱羧曼尼希反应。亚胺底物可通过协作氢键网络激活，以促进β-酮酸的亲核攻击，该网络由氨基磺酸盐诱导的大环催化剂的二聚化组装而实现。高效（>
• 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。
• Base- and metal-free decarboxylative aldol reaction of β-ketoacids with glyoxylate hydrates and glyoxal monohydrates in water
  作者：Nan Ren、Jing Nie、Jun-An Ma

  DOI：10.1039/c6gc02705a

  日期：——

  An environmental benign decarboxylative aldol reaction of [small beta]-ketoacids with glyoxylate and glyoxal monohydrates in water is reported. The reaction proceeds smoothly without any base and metal catalysts, affording the correspoding...

  报道了水中小β-酮酸与乙醛酸酯和乙二醛一水合物的环境良性脱羧醛醇缩合反应。反应平稳进行，无需任何碱和金属催化剂，得到了相应的...
• <i>C</i>₂-Symmetric Chiral Bisoxazolines as Hydrogen-Bond-Acceptor Catalysts in Enantioselective Aldol Reaction of β-Carbonyl Acids with Trifluoroacetaldehyde Hemiacetals
  作者：Zhen-Yan Yang、Jun-Liang Zeng、Nan Ren、Wei Meng、Jing Nie、Jun-An Ma

  DOI：10.1021/acs.orglett.6b03256

  日期：2016.12.16

  C2-symmetric chiral bisoxazoline is demonstrated to use hydrogen bonding to catalyze an important family of aldol reactions of trifluoroacetaldehyde hemiacetals with various β-carbonyl acids. This reaction is highly enantioselective, delivering chiral nonracemic trifluoromethylated alcohols with excellent optical purity and good isolated yields. This concept of relaying chiral information via a chiral hydrogen-bond

  一个简单的C 2对称手性双恶唑啉被证明使用氢键催化三氟乙醛半缩醛与各种β-羰基酸的重要的醛醇缩合反应家族。该反应是高度对映体选择性的，以优异的光学纯度和良好的分离产率提供手性非外消旋三氟甲基化醇。通过手性氢键受体传递手性信息的概念应适用于大量的有机催化过程。
• Copper-Catalyzed One-Pot Denitrogenative-Dehydrogenative-Decarboxylative Coupling of β-Ketoacids with Trifluorodiazoethane: Facile Access to Trifluoromethylated Aldol Products
  作者：Heng-Ying Xiong、Zhen-Yan Yang、Zhen Chen、Jun-Liang Zeng、Jing Nie、Jun-An Ma

  DOI：10.1002/chem.201403073

  日期：2014.7.1

  novel copper‐catalyzed one‐pot cross‐coupling of β‐ketoacids with in situ generated trifluorodiazoethane has been developed. This reaction provides a direct and efficient method, in which one CC bond and one CO bond were formed in a carbenoid center with concomitant denitrogenation–dehydrogenation–decarboxylation, to afford trifluoromethylated aldol products. In several preliminary experiments, good

  已经开发了一种新型的铜催化的β-酮酸与原位生成的三氟重氮乙烷的单锅交叉偶联。该反应提供了一种直接和有效的方法，其中，一种C  C键和一种C 形成在伴随脱氮-脱氢-脱羧卡宾中心O键，得到三氟甲基化的醛醇产品。在一些初步实验中，还获得了良好的对映选择性。