4-(3-methoxyphenyl)-2-phenylthiazole | 1013593-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-methoxyphenyl)-2-phenylthiazole
• 英文别名: 4-(3-Methoxyphenyl)-2-phenyl-1,3-thiazole
• CAS: 1013593-35-5
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: RCDPBXGUUITADI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氨基-(3-甲氧基-苯基)-乙酸 在 劳森试剂 、 甲醇 、 氯化亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 24.0h， 生成 4-(3-methoxyphenyl)-2-phenylthiazole
  参考文献：
  名称：

  Lawesson 试剂促进吖内酯脱氧合成 2,4-二取代噻唑

  摘要：

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。

  DOI：

  10.1039/d2ob01939f

文献信息

• Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction
  作者：Storm Hassell-Hart、Elisa Speranzini、Sirihathai Srikwanjai、Euan Hossack、S. Mark Roe、Daren Fearon、Daniel Akinbosede、Stephen Hare、John Spencer

  DOI：10.1021/acs.orglett.2c02996

  日期：2022.11.4

  A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.

  通过 Ir 催化叶立德插入化学合成了噻唑和硒代噻唑库。这个过程是一个官能团，特别是杂环取代基的耐受性。该技术被应用于合成抗炎药法奈替唑以及与淋病奈瑟菌细菌中的肽基-tRNA水解酶（Pth）结合的含噻唑药物片段。
• 10.1039/d4ra03290j
  作者：Mahaur, Priya、Rajput, Khushbu、Singh, Vishal、Srivastava, Vandana、Singh, Sundaram

  DOI：10.1039/d4ra03290j

  日期：——

  The lipase-catalyzed, ultrasound-assisted synthesis presented in this study represents a greener and more sustainable alternative to traditional synthetic pathways for these important compounds, offering promising potential for applications in medicinal chemistry and drug development. This approach holds the promise of advancing the field of thiazole synthesis, contributing to more sustainable and efficient

  本研究探索了一种有效合成 2,4-二取代噻唑衍生物的创新方法，这是一类具有多种生物学和药物意义的化合物。这项研究表明脂肪酶是一种高效且环境友好的噻唑合成催化剂。在温和的条件下，芳基乙烯酮、KBrO3 和硫代酰胺的缩合是通过使用超声波能量来辅助的。此外，我们利用超声波照射的力量来加速反应，减少反应时间并提高产品产量。本研究中提出的脂肪酶催化、超声辅助合成代表了这些重要化合物传统合成途径的更环保、更可持续的替代方案，为药物化学和药物开发中的应用提供了广阔的前景。这种方法有望推动噻唑合成领域的发展，为更可持续、更高效的化学工艺做出贡献。
• Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1)
  作者：Abdelrahman S. Mayhoub、Laura Marler、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Mark Cushman

  DOI：10.1016/j.bmc.2012.10.006

  日期：2012.12

  NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating alpha-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believed that QR1 inducers can act as cancer chemopreventive agents. Resveratrol (1) is a naturally occurring stilbene derivative that requires a concentration of 21 mu M to double QR1 activity (CD = 21 mu M). The stilbene double bond of resveratrol was replaced with a thiadiazole ring and the phenols were eliminated to provide a more potent and selective derivative 2 (CD = 2.1 mu M). Optimizing the substitution pattern of the two phenyl rings and the central heterocyclic linker led to a highly potent and selective QR1 inducer 9o with a CD value of 0.087 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles
  作者：Gaofeng Yin、Xiaodong Wang、Yuqing Wang、Tao Shi、Yaofu Zeng、Yuying Wang、Xue Peng、Zhen Wang

  DOI：10.1039/d2ob01939f

  日期：——

  Azlactones and thiazoles are common structural motifs and possess diverse applications. A new method for the efficient and straightforward syntheses of 2,4-disubstituted thiazoles from azlactones has been developed. The reaction proceeded via deoxygenation of azlactones by Lawesson's reagent without metal or external additives. A variety of 2,4-disubstituted thiazoles were synthesized with up to 92%

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。