4-hydroxybut-2-yn-1-yl benzoate | 118017-20-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxybut-2-yn-1-yl benzoate
• 英文别名: 1,4-butynediol monobenzoate；4-(benzoyloxy)but-2-yn-1-ol；4-benzoyloxy-but-2-yn-1-ol；4-benzyloxybut-2-yn-1-ol；4-Benzoyloxy-but-2-in-1-ol；4-hydroxy-but-2-ynyl benzoate；4-Benzoyloxybut-2-yn-1-ol；4-hydroxybut-2-ynyl benzoate
• CAS: 118017-20-2
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: VIYKNOQDHKWSFK-UHFFFAOYSA-N

物化性质

• 沸点：
  367.5±22.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxybut-2-yn-1-yl benzoate 在 Lindlar's catalyst 、 palladium-lead 喹啉 、 氢气 作用下， 以 苯 为溶剂， 24.0 ℃ 、101.32 kPa 条件下， 反应 12.0h， 以90%的产率得到4‐hydroxybut‐2‐en‐1‐yl benzoate
  参考文献：
  名称：

  Synthetic research on hepoxilins

  摘要：

  A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-ClCH2C=CCHOHCH=CHCH(2)OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends alternatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B-3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.

  DOI：

  10.1007/bf02503497
• 作为产物：
  描述：

  丁炔二醇 以60的产率得到4-hydroxybut-2-yn-1-yl benzoate
  参考文献：
  名称：

  Method for preparing hydroxamic acids

  摘要：

  使用三号公式化合物的过程：制备一号和二号公式化合物的过程：以及制备三号公式化合物的过程，其中R1-5和J的定义如本文所述。

  公开号：

  US20050272928A1

文献信息

• Alkynyloxy derivatives of 5,8-quinolinedione: Synthesis, in vitro cytotoxicity studies and computational molecular modeling with NAD(P)H:Quinone oxidoreductase 1
  作者：Monika Kadela-Tomanek、Maria Jastrzębska、Bartosz Pawełczak、Ewa Bębenek、Elwira Chrobak、Małgorzata Latocha、Maria Książek、Joachim Kusz、Stanisław Boryczka

  DOI：10.1016/j.ejmech.2016.12.031

  日期：2017.1

  8-quinolinodione antibiotics were the substrate for the NQO1 protein. The structure-activity relationship showed that the 5,8-quinolinedione moiety was responsible for the interaction with the enzyme. In our research, we presented the synthesis, cytotoxic activity and theoretical study of a 5,8-quinolinedione compound as a potential inhibitor of the NQO1 enzyme. Mono and disubstituted alkynyloxy derivatives

  天然的7-氨基-5,8-喹啉二酮抗生素是NQO1蛋白的底物。结构-活性关系表明5，8-喹啉二酮部分负责与酶的相互作用。在我们的研究中，我们介绍了5,8-喹啉二酮化合物作为NQO1酶的潜在抑制剂的合成，细胞毒性活性和理论研究。合成了5,8-喹啉二酮的单取代和二取代的炔氧基衍生物，并通过1 H，13 C NMR，IR和HR-MS光谱进行了表征。还测试了新合成的衍生物的体外生物活性对抗人类癌细胞系。它们显示出高的细胞毒性活性，这取决于取代基的类型和所使用的肿瘤细胞系。此外，选择了两种乳腺癌细胞系MDA-MB-231和MCF-7进行分析，因为它们具有不同的NQO1蛋白水平。已经发现，所有研究的化合物对具有较高NQO1蛋白水平的细胞系的细胞毒性活性都增加了。分子对接用于检查炔氧基衍生物分子与人NAD [P] H-醌氧化还原酶（NQO1）蛋白之间的可能相互作用。计算研究表明，所有对接化合物的5,8-喹
• Use of hydrolases for the synthesis of cyclic amino acids
  作者：Richard C Lloyd、Michael C Lloyd、Mark E.B Smith、Karen E Holt、Jonathan P Swift、Philip A Keene、Stephen J.C Taylor、Raymond McCague

  DOI：10.1016/j.tet.2003.10.116

  日期：2004.1

  The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. In order to elaborate these building blocks into more complex molecules, crystallization and asymmetric hydrogenation were used to define further stereocentres

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。
• Subtype-selective NMDA receptor ligands and the use thereof
  申请人：Warner-Lambert Co.

  公开号：US06218404B1

  公开（公告）日：2001-04-17

  The invention relates to subtype-selective NMDA receptor ligands and the use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neuro-degenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, Parkinson's disease, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.

  该发明涉及亚型选择性NMDA受体配体及其用于治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元丢失，以及治疗包括阿尔茨海默病、肌萎缩性侧索硬化、亨廷顿病和唐氏综合征在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度刺激的不良后果，治疗焦虑、精神病、抽搐、氨基糖苷类抗生素引起的听力损失、偏头痛、慢性疼痛、帕金森病、青光眼、巨细胞病毒性视网膜炎、尿失禁、阿片类药物耐受性或戒断症状，并诱导麻醉，以及增强认知能力。
• Novel Acyclic Nucleotides and Nucleoside 5'-Triphosphates Imitating 2',3'-Dideoxy-2',3'-didehydro nucleotides: Synthesis and Biological Properties
  作者：Elena A. Shirokova、Natalia B. Tarussova、Alexander V. Shipitsin、Dmitry G. Semizarov、Alexander A. Krayevsky

  DOI：10.1021/jm00048a010

  日期：1994.10

  3'-dideoxy-2',3'-didehydronucleoside 5'-triphosphates known as highly potent chain terminators of DNA polymerases. Phosphonates 10a-d were obtained by alternative alkylations of the nucleic bases followed by condensation with ethyl [[(p-tolylsulfonyl)oxy]methyl]phosphonate. Pyrophosphorylation of 10a-d afforded phosphonate diphosphates 9a-d. Their substrate properties were evaluated in cell-free systems containing

  合成了嘧啶和嘌呤9a-d的一系列焦磷酸基（Z）-（膦甲氧基）丁-2-烯基衍生物和相应的膦酸酯10a-d。制备的化合物包含膦酸酯基团（作为α-磷酸酯模拟物）以及模拟2'，3'-dideoxy-2'，3'-deidehydronucleoside 5'-triphosphates中糖基部分的无环残基，被称为高效末端链终止剂。 DNA聚合酶。通过对核酸碱基进行交替烷基化，然后与[[（对甲苯磺酰基）氧基]甲基]膦酸乙酯缩合，获得膦酸酯10a-d。10a-d的焦磷酸化得到膦酸酯二磷酸酯9a-d。在包含各种DNA聚合酶（包括病毒逆转录酶）的无细胞系统中评估了其底物特性。化合物9a-d对HIV-1和AMV逆转录酶表现出良好的终止底物性质。它们显示出高选择性，未被人类DNA聚合酶α和ε，大鼠肝脏的DNA聚合酶β，大肠杆菌DNA聚合酶I以及HSV-1和CMV DNA聚合酶识别。膦酸酯10b-d在HIV-1感
• Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols
  作者：Zhengwang Chen、Guotian Luo、Yuelu Wen、Yejuan Fu、Hai Chen、Min Ye

  DOI：10.1055/s-0036-1588399

  日期：——

  Graphene oxide was found to be an efficient and reusable acid catalyst for the esterification reaction. A wide range of aliphatic and aromatic acids and alcohols were compatible with the standard conditions and afforded the corresponding products in good yields. The heterogeneous catalyst can be easily recovered and recycled in dichloro­ethane solvent with good catalytic activity.

  发现氧化石墨烯是酯化反应的有效且可重复使用的酸催化剂。范围广泛的脂肪族和芳香族酸和醇与标准条件相容，并以良好的收率提供相应的产品。多相催化剂在二氯乙烷溶剂中易于回收和循环使用，具有良好的催化活性。