ethyl 3-oxo-4-(propionyloxy)butanoate | 104151-55-5

• 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: ethyl 3-oxo-4-(propionyloxy)butanoate
• 英文别名: Ethyl 4-propionyloxy-3-oxobutyrate；ethyl 3-oxo-4-propanoyloxybutanoate
• CAS: 104151-55-5
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: KSRJSPHEMVSGCA-UHFFFAOYSA-N

物化性质

• 沸点：
  266.2±20.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-ynoate 在 4-二甲氨基吡啶 、 三苯基膦氯金 、 水 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 ethyl 3-oxo-4-(propionyloxy)butanoate
  参考文献：
  名称：

  Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates

  摘要：

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

  DOI：

  10.1021/acs.joc.5b00400

文献信息

• Process for the preparation of 4-acyloxy-3-oxo-butyric acid esters
  申请人：Bayer Aktiengesellschaft

  公开号：US04720572A1

  公开（公告）日：1988-01-19

  A process for the preparation of a 4-acyloxy-3-oxo-butyric acid ester of the formula ##STR1## in which R.sup.1 is alkyl with up to 4 C atoms, and R.sup.2 is alkyl with up to 4 C atoms and optionally substituted by halogen, hydroxyl, alkoxy or phenyl, or is aryl, which comprises reacting a 4-halogenobutyric acid ester of the formula ##STR2## in which X is chlorine or bromine, with a carboxylic acid of the formula ##STR3## in the presence of acid-trapping agent in an organic solvent at a temperature of between 0.degree. and 170.degree. C.

  一种制备式为##STR1##的4-酰氧基-3-酮丁酸酯的方法，其中R.sup.1是具有最多4个碳原子的烷基，R.sup.2是具有最多4个碳原子的烷基，可选择地被卤素、羟基、烷氧基或苯基取代，或者是芳基，包括在有机溶剂中，在0°C至170°C的温度下，在酸俘获剂的存在下，将式为##STR2##的4-卤代丁酸酯与式为##STR3##的羧酸反应。
• [EN] METHYL (R) -2- (FLUOROMETHYL) -5-OXO-4-PHENYL-4, 5, 6, 7-TETRAHYDRO-1H-CYCLOPENTA [B] PYRIDINE-3-CARBOXYLATE AND METHYL (R) -2- (FLUOROMETHYL) -5-OXO-4-PHENYL-1, 4, 5, 7-TETRAHYDROFURO [3, 4-B] PYRIDINE-3-CARBOXYLATE AS CAV1.2 ACTIVATORS<br/>[FR] MÉTHYL(R)-2-(FLUOROMÉTHYL)-5-OXO-4-PHÉNYL-4,5,6, 7-TÉTRAHYDRO-1H-CYCLOPENTA[B]PYRIDINE-3-CARBOXYLATE ET MÉTHYL(R)-2-(FLUOROMÉTHYL)-5-OXO-4-PHÉNYL-1,4,5,7-TÉTRAHYDROFURO[3,4-B]PYRIDINE-3-CARBOXYLATE UTILISÉS EN TANT QU'ACTIVATEURS DE CAV1.2
  申请人：NOVARTIS AG

  公开号：WO2021253180A1

  公开（公告）日：2021-12-23

  Provided herein is a compound according to formula (I) or a pharmaceutically acceptable salt thereof as CaV1.22 activators for the treatment of schizophrenia, bipolar disorder, major depressive disorder, substance use disorder, ADHD, Phelan-McDermid Syndrome, autism spectrum disorder, multiple sclerosis, frontotemporal dementia, Alzheimer's disease, Brugada Syndrome, Short QT syndrome, or early repolarization syndrome.

  本文提供了一种按照式(I)的化合物或其药用可接受的盐，作为CaV1.22激活剂，用于治疗精神分裂症、双相情感障碍、重度抑郁症、物质使用障碍、注意力缺陷多动障碍、费兰-麦德米德综合征、自闭症谱系障碍、多发性硬化、额颞叶痴呆、阿尔茨海默病、布鲁加达综合征、短QT综合征或早复极化综合征的治疗。
• US4188395A
  申请人：——

  公开号：US4188395A

  公开（公告）日：1980-02-12
• US4720572A
  申请人：——

  公开号：US4720572A

  公开（公告）日：1988-01-19
• Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates
  作者：Tapas R. Pradhan、Kishor L. Mendhekar、Debendra K. Mohapatra

  DOI：10.1021/acs.joc.5b00400

  日期：2015.6.5

  The At(I)-catalyzed regioselective hydration of gamma-acetoxy-alpha,beta-acetylinic ester by the assistance of a neighboring carbonyl group has beets developed. Varieties of simple primary, secondary, and tertiary gamma-acetoxy-alpha,beta-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding beta-keto esters. The reaction' tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. O-18 labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.