4-phenylbut-2-ynoic acid ethyl ester | 96417-50-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-phenylbut-2-ynoic acid ethyl ester
• 英文别名: 4-Phenyl-butin-2-saeure-ethylester；Ethyl 4-phenylbut-2-ynoate
• CAS: 96417-50-4
• 化学式: C₁₂H₁₂O₂
• mdl: MFCD26407578
• 分子量: 188.226
• InChiKey: FTCCQRCYCSPLDX-UHFFFAOYSA-N

物化性质

• 沸点：
  310.7±21.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylbut-2-ynoic acid ethyl ester 在 三氟化硼乙醚 、 氯甲酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 5-Acetylamino-1-benzyl-6-oxo-2-[1-phenyl-meth-(E)-ylidene]-piperidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Formation of Dihydropyridone- and Pyridone-Based Peptide Analogs through Aza-Annulation of β-Enamino Ester and Amide Substrates with α-Amido Acrylate Derivatives

  摘要：

  The aza-annulation of beta-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted alpha-acetamido delta-lactam products. With the alpha-acetamido substituent, lactam functionality, and gamma-carboxylate group, these delta-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an alpha-amino acid coupled with a beta-amino acid. When alpha-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique beta-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an alpha-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.

  DOI：

  10.1021/jo9600520
• 作为产物：
  描述：

  乙醇 、 4-phenylbut-2-ynoic acid 在 对甲苯磺酸 作用下， 生成 4-phenylbut-2-ynoic acid ethyl ester
  参考文献：
  名称：

  1023.丙二烯天然合成的模型

  摘要：

  DOI：

  10.1039/jr9630005356

文献信息

• Diastereoselective synthesis of cyclopentene spiro-rhodanines containing three contiguous stereocenters via phosphine-catalyzed [3 + 2] cycloaddition or one-pot sequential [3 + 2]/[3 + 2] cycloaddition
  作者：Jiayong Zhang、Minxuan Zhang、Yuming Li、Shang Liu、Zhiwei Miao

  DOI：10.1039/c6ra23399f

  日期：——

  form cyclopentene spiro-rhodanine scaffolds are described. In the first approach, alkynoate derivatives and 5-arylidene-3-(tert-butyl)-2-thioxothiazolidin-4-one react in the presence of PBu3 through a [3+2]...

  描述了两种不同的非对映选择性膦催化的级联反应，以形成环戊烯螺-罗丹宁骨架。在第一种方法中，炔醇酸酯衍生物和5-亚芳基-3-（叔丁基）-2-硫代噻唑啉酮-4-酮在PBu3存在下通过[3 + 2]发生反应。
• Effect of Multinuclear Copper/Aluminum Complexes in Highly Asymmetric Conjugate Addition of Trimethylaluminum to Acyclic Enones
  作者：Kohei Endo、Daisuke Hamada、Sayuri Yakeishi、Takanori Shibata

  DOI：10.1002/anie.201206297

  日期：2013.1.7

  Al and friends: Asymmetric conjugate addition of Me3Al to β,β‐disubstituted α,β‐unsaturated ketones in the presence copper and L1 leads to a highly efficient construction of an all‐carbon‐substituted chiral quaternary center. This result is the first example of an asymmetric conjugate addition of Me3Al to acyclic enones to give a chiral quaternary carbon center with excellent yield and enantioselectivity

  Al和朋友：在铜和L1存在下，Me 3 Al不对称地共轭添加到β，β-二取代的α，β-不饱和酮中，导致高效构建全碳取代的手性季中心。该结果是在温和的反应条件下将Me 3 Al不对称共轭加成到无环烯酮上以得到具有优异收率和对映选择性的手性季碳中心的第一个例子。
• Et3N-catalyzed direct cycloaddition reaction of allenoates with acceptor diazo compounds
  作者：Yu-Ting Tian、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1016/j.tet.2021.131922

  日期：2021.2

  A Et3N-catalyzed [3 + 2] cycloaddition reaction of allenoates with acceptor diazo compounds that include diazoesters, diazoketones, and diazoamides, has been developed. This transformation allows direct and regioselective synthetic route to a variety of pyrazoles from allenoates. 3-Alkynoates also participate in the cycloaddition reaction by isomerizing to the corresponding allenoates in situ.

  己烯酸酯与包括重氮酯，重氮酮和重氮酰胺的受体重氮化合物的Et 3 N催化的[3 + 2]环加成反应已得到开发。这种转化允许直接和区域选择性地合成路线从烯丙酸酯到各种吡唑。3-炔酸酯还通过异构化成相应的烯丙基酸酯而参与环加成反应。
• Exposure to a Deuterated Analogue of Phenylbutyrate Retards S-Phase Progression in HT-29 Colon Cancer Cells
  作者：Kevin O. Clarke、Susan M. Ludeman、James B. Springer、O.Michael Colvin、Michael A. Lea、Lawrence E. Harrison

  DOI：10.1002/jps.10102

  日期：2002.4

  Interestingly, exposure of HT-29 colon cancer cells to D4PB resulted in a slowing of S transit, in contrast to butyrate and PB, which induced a G2/M cell cycle block. This difference in cell cycle effect may explain the differences seen in the potency of the phenotypic changes seen with treatment with D4PB. Further studies are needed to elucidate the mechanisms underlying effects of D4PB on the cell cycle.

  在不显着影响正常细胞的情况下，诱导肿瘤细胞恢复正常表型和/或引起生长停滞的分化剂代表了癌症治疗的诱人选择。短链脂肪酸的类似物，例如苯丁酸苯酯（PB），已作为临床相关药物进行了研究。为了改善其药代动力学特性，已经研究了PB和其他脂肪酸的结构修饰。我们假设PB的战略性同位素修饰将导致更长的半衰期，从而转化为更有效的临床分化剂。使用结肠癌模型，我们证明与PB和丁酸相比，2,2,3,3-四氘代PB（D4PB）显着增加了细胞凋亡的诱导和细胞增殖的抑制。D4PB对凋亡级联反应的特定调节蛋白表达的影响或D4PB对组蛋白脱乙酰基酶活性的抑制作用无法解释效力的差异。有趣的是，HT-29结肠癌细胞暴露于D4PB导致S转运减慢，而丁酸和PB则引起G2 / M细胞周期阻滞。细胞周期效应的这种差异可以解释用D4PB治疗所见表型变化的效力差异。需要进一步的研究以阐明D4PB对细胞周期的影响的潜在机制。HT-29结肠癌
• [EN] IMIDAZOLE COMPOUND<br/>[FR] COMPOSÉ D'IMIDAZOLE<br/>[ZH] 咪唑类化合物
  申请人：GUANGDONG ZHONGSHENG PHARMACEUTICAL CO LTD

  公开号：WO2016169514A1

  公开（公告）日：2016-10-27

  本发明公开了一种咪唑类化合物，具体公开了式(I)所示的化合物、其药学上可接受的盐或其互变异构体。