(Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone | 128858-50-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone
• 英文别名: (4Z)-2-methyl-4-(1-naphthylmethylene)oxazol-5-one；(4Z)-2-methyl-4-(naphthalen-1-ylmethylidene)-1,3-oxazol-5-one
• CAS: 128858-50-4
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: SOZGZXBLNWADNY-ZROIWOOFSA-N

物化性质

• 熔点：
  159.0-160.0 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  395.8±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone 在 盐酸 、 sodium hydroxide 作用下， 生成 3-(naphthalene-1-yl)-2-oxopropanoic acid
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t
• 作为产物：
  描述：

  N-acetyl-α-dehydro(1-naphthyl)alanine 1-naphthyl ester 以 乙腈 为溶剂， 生成 (Z)-2-methyl-4-(1-naphthylmethylene)-5(4H)-oxazolone
  参考文献：
  名称：

  A Photoinduced Refractive Index Increase in Poly(methyl methacrylate) Film Doped with N-Acetyl-α-dehydroarylalanine Naphthyl Esters

  摘要：

  DOI：

  10.1021/ma051116o

文献信息

• Electron transfer-initiated asymmetric photocyclization of chiral auxiliary-substituted N-acyl-α-dehydro(1-naphthyl)alaninamides to the corresponding 3,4-dihydrobenzo[f]quinolinone derivatives
  作者：Kei Maekawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2005.09.042

  日期：2005.11

  olinone derivatives (2) in excess at rt, respectively. The magnitude of diastereomeric excess (de) was varied in the range of −5–26% for (R,S)-2 and 16–92% for (S,S)-2, depending on the chiral auxiliary and reaction temperature. The mechanism of asymmetric induction in the photocyclization process eventually affording diastereomeric 2 was discussed based on solvent, tertiary amine, chiral auxiliary

  在含有叔胺的甲醇中，标题为N-酰基-α-脱氢萘丙氨酰胺[（Z）-1 ]与（S）-1-苯基乙氨基和（S）-丙氨酰胺辅助基的光诱导电子转移反应显示形成（R，在室温下分别过量的S）-和（S，S）-3,4-二氢苯并[ f ]喹啉酮衍生物（2）。（R，S）-2的非对映体过量（de）的幅度在-5–26％的范围内，而（S，S）-的非对映体过量（de）的范围在16–92％的范围内2，取决于手性助剂和反应温度。基于溶剂，叔胺，手性助剂和温度对de值的影响以及非对映体烯醇中间体的MM2和PM5计算，讨论了最终提供非对映体2的光环化过程中的不对称诱导机理。
• Efficient Formation of a Triazole Ring via Novel Ring-Opening Reaction of (Z)-2-Methyl-4-arylmethylene-5(4H)-oxazolones with Hydrazides
  作者：Tadamitsu Sakurai、Kei Maekawa、Atsushi Tomoda、Tetsutaro Igarashi

  DOI：10.3987/com-08-11457

  日期：——

  mechanistic points of view. It was found that the novel ring-opening reaction proceeded to give (Z)-2-(3-methyl-5-substituted 1,2,4-triazol-4-yl)-3-aryl-2-propenoic acids (1,2,4-triazole-substituted (Z)-α-dehydroarylalanines| as major products, along with minor or negligible amounts of their isomers. Substituent and solvent effects on the relative composition of these two isomers confirmed that this

  从合成和机理的角度研究了标题恶唑酮与酰肼亲核试剂的开环模式。发现新的开环反应进行得到（Z）-2-（3-甲基-5-取代的1,2,4-三唑-4-基）-3-芳基-2-丙烯酸（1 ,2,4-三唑取代的 (Z)-α-脱氢芳基丙氨酸|作为主要产物，以及少量或可忽略不计的异构体。取代基和溶剂对这两种异构体的相对组成的影响证实了该组成取决于空间位阻芳基（在恶唑酮中）和酰基（在酰肼亲核试剂中）取代基以及溶剂极性的电子因素。
• A novel route to 2-imidazolin-5-one derivatives via oxidative cyclization of aryl-substituted (Z)-N-acetyl-α-dehydroalanines having a dialkylamino group
  作者：Atsushi Kawasaki、Kei Maekawa、Kanji Kubo、Tetsutaro Igarashi、Tadamitsu Sakurai

  DOI：10.1016/j.tet.2004.07.068

  日期：2004.10

  It was found that the reaction of the title compounds [(Z)-1] with oxygen in methanol proceeds according to the first-order kinetics to give (Z)-2-imidazolin-5-one derivatives and hydrogen peroxide in quantitative yields. Analysis of substituent and solvent effects on the rate constant for this oxidative cyclization led us to propose that electron transfer from the dialkylamino nitrogen in (Z)-1 to

  发现标题化合物[（Z）-1 ]与氧气在甲醇中的反应根据一级动力学进行，以定量产率得到（Z）-2-咪唑啉-5-酮衍生物和过氧化氢。分析取代基和溶剂对这种氧化环化反应的速率常数的影响，导致我们提出电子从（Z）-1中的二烷基氨基氮转移到氧，超氧化物提取酰胺-质子以及随后的分子内电子转移都是-确定步骤。讨论了芳基取代的（Z）-N-乙酰基-α-脱氢丙氨酸衍生物新型环化反应的合成实用性。
• Practical Preparation of <i>Z</i>‐α‐(<i>N</i>‐Acetylamino)‐ and <i>Z</i>‐α‐(<i>N</i>‐Benzoylamino)‐α,β‐unsaturated Acids
  作者：Branko S. Jursic、Sarada Sagiraju、Dustin K. Ancalade、Traneil Clark、Edwin D. Stevens

  DOI：10.1080/00397910701265895

  日期：2007.5.1

  An efficient two‐step synthetic procedure for the preparation of numerous variations of N‐protected α,β‐unsaturated α‐amino acids and their corresponding esters from N‐protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N‐protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base.

  摘要 开发了一种有效的两步合成程序，用于从 N-保护的甘氨酸和脂肪族或芳香族醛制备 N-保护的 α,β-不饱和 α-氨基酸及其相应的酯的多种变体。该反应包括将 N 保护的甘氨酸环化为恶唑酮、与醛缩合以及与碱开环。
• Green fluorescent protein chromophore derivatives as a new class of aldose reductase inhibitors
  作者：Ryota Saito、Maiko Hoshi、Akihiro Kato、Chikako Ishikawa、Toshiya Komatsu

  DOI：10.1016/j.ejmech.2016.10.016

  日期：2017.1

  copounds with an IC50 value of 0.10 μM. Structure-activity relationship studies combined with docking simulations revealed the interaction mode of the newly synthesized inhibitors toward the target protein as well as the structural features required to gain a high inhibitory activity. In conclusion, the GFP chromophore model compounds synthesized in this study have proved to be potential drugs for diabetic

  已合成了许多与水母绿色荧光蛋白（GFP）的荧光发色团有关的（Z）-4-芳基亚甲基-1 H-咪唑-5（4 H）-，并对其体外抑制作用进行了评估。重组人醛糖还原酶的活性首次获得证实。GFP生色团模型1a在4-亚苄基上具有对羟基，在N1位置上具有羧甲基，具有很强的生物活性，IC 50值为0.36μM。该功效高于已知的高效醛糖还原酶抑制剂山梨醇的功效。化合物1h，即1a的2-萘基亚甲基类似物，在被测化合物中表现出最佳的抑制作用，IC 50值为0.10μM 。结构-活性关系研究与对接模拟相结合，揭示了新合成的抑制剂与靶蛋白的相互作用模式以及获得高抑制活性所需的结构特征。总之，本研究中合成的GFP生色团模型化合物已被证明是糖尿病并发症的潜在药物。