(E)-1-(benzo[b]thiophen-2-yl)-3-phenylprop-2-en-1-one | 93486-61-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(benzo[b]thiophen-2-yl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(1-benzothiophen-2-yl)-3-phenylprop-2-en-1-one
• CAS: 93486-61-4
• 化学式: C₁₇H₁₂OS
• 分子量: 264.348
• InChiKey: MIYWYYPJOPEBHY-ZHACJKMWSA-N

物化性质

• 熔点：
  119-122 °C
• 沸点：
  442.8±37.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(benzo[b]thiophen-2-yl)-3-phenylprop-2-en-1-one 以36%的产率得到
  参考文献：
  名称：

  SKRAMSTAD, J.;SLETTEN, T., ACTA CHEM. SCAND., 1984, 38, N 4, 319-322

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-(3'-phenyl-2'-propen-1'-hydroxy)-benzothiophene 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以44%的产率得到(E)-1-(benzo[b]thiophen-2-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Skramstad, Jan; Sletten, Tore, Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry, 1984, vol. 38, # 4, p. 319 - 322

  摘要：

  DOI：

文献信息

• Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based <i>Cinchona</i> Alkaloids as Hybrid Phase-Transfer Catalysts
  作者：Maciej Majdecki、Agata Tyszka-Gumkowska、Janusz Jurczak

  DOI：10.1021/acs.orglett.0c03272

  日期：2020.11.6

  99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading

  使用杂化的基于酰胺的金鸡纳生物碱，以优异的收率（高达99％）和对映选择性（高达> 99％ee）获得了一系列20种手性环氧化物。我们的方法的特点是催化剂负载量低（0.5摩尔％），反应时间短。此外，环氧化过程可以在10个循环中进行，而无需将催化剂进一步添加到反应混合物中。使用非常低的催化剂负载量，该方法可以显着提高工艺规模。
• New Zileuton-Hydroxycinnamic Acid Hybrids: Synthesis and Structure-Activity Relationship towards 5-Lipoxygenase Inhibition
  作者：Audrey Isabel Chiasson、Samuel Robichaud、Fanta J. Ndongou Moutombi、Mathieu P. A. Hébert、Maroua Mbarik、Marc E. Surette、Mohamed Touaibia

  DOI：10.3390/molecules25204686

  日期：——

  zileuton-hydroxycinnamic acid hybrids were synthesized and screened as 5-lipoxygenase (5-LO) inhibitors in stimulated HEK293 cells and polymorphonuclear leukocytes (PMNL). Zileuton’s (1) benzo[b]thiophene and hydroxyurea subunits combined with hydroxycinnamic acid esters’ ester linkage and phenolic acid moieties were investigated. Compound 28, bearing zileuton’s (1) benzo[b]thiophene and sinapic acid phenethyl ester’s

  合成了一系列新的齐留通-羟基肉桂酸杂化物，并在刺激的 HEK293 细胞和多形核白细胞 (PMNL) 中将其筛选为 5-脂氧合酶 (5-LO) 抑制剂。研究了齐留通 (1) 苯并 [b] 噻吩和羟基脲亚基与羟基肉桂酸酯的酯键和酚酸部分的结合。带有齐留通 (1) 苯并[b]噻吩和芥子酸苯乙酯 (2) α,β-不饱和酚酸部分 28 的化合物 28 被证明与齐留通 (1) 等效，齐留通 (1) 是唯一经临床批准的 5-LO 抑制剂, 在受刺激的 HEK293 细胞中。化合物 28 在 PMNL 中抑制 5-LO 的活性是齐留通 (1) 的三倍。带有与 28 相同的芥子酸（3,5-二甲氧基-4-羟基取代）部分的化合物 37 与齐留通的 (1) 羟基脲亚基组合是无活性的。该结果表明齐留通 (1) 苯并 [b] 噻吩部分对于抑制 5-LO 产物与我们的氢化物的生物合成至关重要。与齐留通 (1) 不同，化合物
• Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition
  作者：Luoqiang Zhang、Mengxin Zhao、Maoping Pu、Zhaoming Ma、Jingsong Zhou、Caiyou Chen、Yun-Dong Wu、Yonggui Robin Chi、Jianrong Steve Zhou

  DOI：10.1021/jacs.2c05678

  日期：2022.11.9

  A nickel complex of isoquinox promoted enantioselective conjugate arylation and heteroarylation of enones using aryl and heteroaryl halides directly. The reaction was successfully applied to stereoselective syntheses of ar-turmerone, chiral fragments of (+)-tolterodine and AZD5672. Mechanistically, experiments and calculations supported that an arylnickel(I) complex inserted to enones via an elementary

  异喹诺酮的镍络合物直接使用芳基和杂芳基卤化物促进烯酮的对映选择性共轭芳基化和杂芳基化。该反应成功应用于ar -turmerone、(+)-tolterodine和AZD5672手性片段的立体选择性合成。从机理上讲，实验和计算支持芳基镍 (I) 络合物通过基本 1,4-加成插入到烯酮中。
• Substituted Benzothiophene or Benzofuran Derivatives as a Novel Class of Bone Morphogenetic Protein-2 Up-Regulators: Synthesis, Structure−Activity Relationships, and Preventive Bone Loss Efficacies in Senescence Accelerated Mice (SAMP6) and Ovariectomized Rats
  作者：Hui-fang Guo、Hua-yi Shao、Zhao-yong Yang、Si-tu Xue、Xue Li、Zong-ying Liu、Xiao-bo He、Jian-dong Jiang、Yue-qin Zhang、Shu-yi Si、Zhuo-rong Li

  DOI：10.1021/jm901685n

  日期：2010.2.25

  In this work, substituted benzothiophene and benzofuran compounds were found to be a new class of potential anabolic agents by enhancing BMP-2 expression. A series of benzothiophene and benzofuran derivatives have been synthesized, and their activities of up-regulating BMP-2 and bone loss prevention efficacies in SAMP6 mice and OVX rats have been studied. Benzothiophenes 1, 3, 14, 4a, 7a, 8a, and benzofuran analogue 2 showed higher BMP-2 up-regulation rates in vitro. Compound 8111 was found to significantly affect the bone formation rate of tested SAMP6 mice. Compound I showed an improved bone quality in SAMP6 mice and also showed activity in OVX rats. We have demonstrated that Substituted benzothiophene and benzofuran derivatives, especially compounds I and 8a, enhance BMP-2 expression in vitro and in vivo and stimulate bone formation and trabecular connectivity restoration ill vivo. The compounds represent potential leads in the development of a new class of anabolic agents.
• SKRAMSTAD, J.;SLETTEN, T., ACTA CHEM. SCAND., 1984, 38, N 4, 319-322
  作者：SKRAMSTAD, J.、SLETTEN, T.

  DOI：——

  日期：——