1-(methoxycarbonyl)-2-(thiophen-2-yl)cyclopropanecarboxylic acid | 1387517-41-0

• 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: 1-(methoxycarbonyl)-2-(thiophen-2-yl)cyclopropanecarboxylic acid
• 英文别名: 1-Methoxycarbonyl-2-thiophen-2-ylcyclopropane-1-carboxylic acid；1-methoxycarbonyl-2-thiophen-2-ylcyclopropane-1-carboxylic acid
• CAS: 1387517-41-0
• 化学式: C₁₀H₁₀O₄S
• 分子量: 226.253
• InChiKey: BPFHFGZAKQSKPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(methoxycarbonyl)-2-(thiophen-2-yl)cyclopropanecarboxylic acid 在 sodium azide 、 氯化铵 作用下， 以 甲乙醚 、 水 为溶剂， 反应 2.0h， 以79%的产率得到methyl 4-azido-4-(thiophen-2-yl)butanoate
  参考文献：
  名称：

  Tandem Ring-Opening Decarboxylation of Cyclopropane Hemimalonates with Sodium Azide: A Short Route to γ-Aminobutyric Acid Esters

  摘要：

  Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce gamma-azidobutyric acids in good yields. These adducts were hydrogenated to form gamma-aminobutyric acid (GABA) methyl esters.

  DOI：

  10.1021/jo3010606

文献信息

• Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine
  作者：Jun-An Xiao、Peng-Ju Xia、Xing-Yu Zhang、Xiao-Qing Chen、Guang-Chuan Ou、Hua Yang

  DOI：10.1039/c5cc07485a

  日期：——

  A highly diastereoselective intramolecular [3+2] annulation via the ring-opening of cyclopropane diester derivative has been developed to construct dihydroquinoline scaffold. A series of tricyclic dihydroquinolines bearing one or two all-carbon...

  已经开发了通过环丙烷二酯衍生物的开环的高度非对映选择性的分子内[3 + 2]环空反应来构建二氢喹啉骨架。一系列带有一个或两个全碳原子的三环二氢喹啉。
• γ-Substituted Butanolides from Cyclopropane Hemimalonates: An Expedient Synthesis of Natural (<i>R</i>)-Dodecan-4-olide
  作者：Huck K. Grover、Michael R. Emmett、Michael A. Kerr

  DOI：10.1021/ol402252u

  日期：2013.9.20

  hemimalonates has led to the facile synthesis of γ-substituted butanolides. Under microwave irradiation, cyclopropane hemimalonates undergo rapid conversion to butanolides in the presence of inorganic salts with an unprecedented retention of stereochemistry. This unique process has been applied to the total synthesis of the naturally occurring (R)-dodecan-4-olide.

  对供体-受体环丙烷半棉酸酯的反应性的探索导致了γ-取代丁醇化物的简便合成。在微波辐射下，在无机盐的存在下，环丙烷半棉酸酯迅速转化为丁醇化物，并保持了前所未有的立体化学。该独特的方法已应用于天然存在的（R）-dodecan-4-olide的全合成。
• Tandem Ring-Opening Decarboxylation of Cyclopropane Hemimalonates with Sodium Azide: A Short Route to γ-Aminobutyric Acid Esters
  作者：Michael R. Emmett、Huck K. Grover、Michael A. Kerr

  DOI：10.1021/jo3010606

  日期：2012.8.3

  Cyclopropane hemimalonates, when treated with sodium azide, undergo a tandem ring-opening decarboxylation to produce gamma-azidobutyric acids in good yields. These adducts were hydrogenated to form gamma-aminobutyric acid (GABA) methyl esters.