4-(6-methoxy-2-naphthyl)-3-butene-2-ol | 127053-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(6-methoxy-2-naphthyl)-3-butene-2-ol
• 英文别名: 4-(6-Methoxynaphthalen-2-yl)but-3-en-2-ol；(E)-4-(6-methoxynaphthalen-2-yl)but-3-en-2-ol
• CAS: 127053-21-8
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: QAYZDAXFEPEODY-ONEGZZNKSA-N

物化性质

• 沸点：
  412.2±25.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(6-methoxy-2-naphthyl)-3-butene-2-ol 在 17β-hydroxysteroid-dehydrogenase type 10 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 生成 (E)-4-(6-甲氧基-2-萘基)-3-丁烯-2-酮
  参考文献：
  名称：

  Harnessing Functional Plasticity of Enzymes:  A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases

  摘要：

  In this paper, we describe the development of a fluorogenic substrate for 17 beta-hydroxysteroid-dehydrogenase, type 10(17 beta-HSD10), which is a multifunctional metabolic enzyme fulfilling several metabolic roles beta-oxidation of fatty acids, catabolism of isoleucine, and metabolism of steroids). In recent years, it has emerged as an important stress and pathological marker in neurons and glial cells (expression downregulation in Parkinson's disease, up-regulation and association with beta-amyloid peptide in Alzheimer's disease). Through the iterative molecular design and chemical synthesis described herein, compound I was developed, which possesses all required properties for a selective optical reporter substrate: alcohol-ketone optical switching, the ability to function as a good enzyme substrate (expressed in kinetic parameters), cell permeability, and cell retention. Probe 1 provides a blue-to-green/yellow bright switch and enables non-invasive, real-time imaging of 17 beta-HSD10 in live human cells. The selectivity of reporter 1 was established by the quantitative correlation of metabolic activity to protein expression in human kidney cell line HEK-293T.

  DOI：

  10.1021/ja072601x
• 作为产物：
  描述：

  (E)-4-(6-甲氧基-2-萘基)-3-丁烯-2-酮 在 cerium(III) chloride 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以85%的产率得到4-(6-methoxy-2-naphthyl)-3-butene-2-ol
  参考文献：
  名称：

  Harnessing Functional Plasticity of Enzymes:  A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases

  摘要：

  In this paper, we describe the development of a fluorogenic substrate for 17 beta-hydroxysteroid-dehydrogenase, type 10(17 beta-HSD10), which is a multifunctional metabolic enzyme fulfilling several metabolic roles beta-oxidation of fatty acids, catabolism of isoleucine, and metabolism of steroids). In recent years, it has emerged as an important stress and pathological marker in neurons and glial cells (expression downregulation in Parkinson's disease, up-regulation and association with beta-amyloid peptide in Alzheimer's disease). Through the iterative molecular design and chemical synthesis described herein, compound I was developed, which possesses all required properties for a selective optical reporter substrate: alcohol-ketone optical switching, the ability to function as a good enzyme substrate (expressed in kinetic parameters), cell permeability, and cell retention. Probe 1 provides a blue-to-green/yellow bright switch and enables non-invasive, real-time imaging of 17 beta-HSD10 in live human cells. The selectivity of reporter 1 was established by the quantitative correlation of metabolic activity to protein expression in human kidney cell line HEK-293T.

  DOI：

  10.1021/ja072601x

文献信息

• Arylation of Allyl Alcohols in Organic and Aqueous Media Catalyzed by Oxime-Derived Palladacycles: Synthesis of β-Arylated Carbonyl Compounds
  作者：Emilio Alacid、Carmen Nájera

  DOI：10.1002/adsc.200700301

  日期：2007.12.10

  oxime-derived palladacycle catalyzes the Mizoroki–Heck reaction of allyl alcohols with aryl iodides, bromides, and chlorides in aqueous and organic solvents. The reaction takes place in the presence of dicyclohexylmethylamine or cesium carbonate as bases, the addition of tetrabutylammonium bromide (TBAB) as additive for aryl bromides and chlorides being necessary. Under these reaction conditions, β-arylated aldehydes

  在水性和有机溶剂中，一种4-羟基苯乙酮肟肟酸酯衍生物可催化烯丙醇与芳基碘化物，溴化物和氯化物的Mizoroki-Heck反应。该反应在二环己基甲胺或碳酸铯作为碱的存在下进行，必须添加四丁基溴化铵（TBAB）作为芳基溴化物和氯化物的添加剂。在这些反应条件下，β-芳基化的醛和酮主要是使用相当低的钯含量（0.1-1 mol％）获得的。源自Kaiser肟树脂的palladacycle具有相似的催化活性，该化合物可以进行低Pd浸出的回收和再利用实验。观察到的高区域选择性和化学选择性支持这些palladacycles作为Pd（0）物种的来源，主要通过中立机制运作。该方法已应用于重要的β-芳基羰基化合物的合成，例如4-苯基丁-2-酮，4-（4-羟基苯基）丁-2-酮，二氢查耳酮，抗炎萘丁美酮和芳香剂。 β-lilial®。在烯丙醇和丁-3-烯-2-醇与2-碘苯胺的反应中观察到γ-芳基化，主要产生相应的喹啉
• Phosphites as Ligands for Efficient Catalysis of Heck Reactions
  作者：Matthias Beller、Alexander Zapf

  DOI：10.1055/s-1998-1760

  日期：1998.7

  The palladium-catalyzed Heck reaction of aryl halides in the presence of phosphite ligands is described for the first time. Aryl bromides and even electron deficient aryl chlorides can be coupled efficiently (turnover numbers up to 31 000) with different olefins using palladium/trialkyl- or triaryl phosphite mixtures as catalysts.

  首次报道了在膦配体存在下，钯催化的芳基卤化物 Heck 反应。使用钯/三烷基或三芳基膦混合物作为催化剂，芳基溴化物甚至低电子活性的芳基氯化物都能够与不同烯烃有效地偶联（周转次数高达31,000次）。
• Convenient Syntheses of Nabumetone
  作者：Mohammad Aslam、Varadaraj Elango、Kenneth G. Davenport

  DOI：10.1055/s-1989-27417

  日期：——

  Two novel and convergent one- and two-step syntheses of 4-(6′-methoxy-2′-naphthyl) -2-butanone (nabumetone, 6) via palladium-catalyzed coupling of 2-halo-6-methoxynaphthalene (1) with 3-buten-2-ol (2) and 3-buten-2-one (3) are described. The product is obtained in 60-92% yield.

  本研究描述了通过钯催化 2-卤代-6-甲氧基萘（1）与 3-丁烯-2-醇（2）和 3-丁烯-2-酮（3）的偶联，一步和两步合成 4-(6′-甲氧基-2′-萘基) -2-丁酮（萘丁美酮，6）的两种新颖和趋同的方法。产物的收率为 60-92%。
• ASLAM, MOHAMMAD;ELANGO, VARADARAJ;DAVENPORT, KENNETH G., SYNTHESIS (BRD),(1989) N1, C. 869-870
  作者：ASLAM, MOHAMMAD、ELANGO, VARADARAJ、DAVENPORT, KENNETH G.

  DOI：——

  日期：——
• PRODUCTION OF NABUMETONE OR PRECURSORS THEREOF
  申请人：ALBEMARLE CORPORATION

  公开号：EP0937021A1

  公开（公告）日：1999-08-25