5-(naphthalen-2-yl)thiophene-2-carbaldehyde | 479243-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-2-yl)thiophene-2-carbaldehyde
• 英文别名: 5-(naphth-2-yl)thienyl-2-carbaldehyde；5-Naphthalen-2-ylthiophene-2-carbaldehyde
• CAS: 479243-40-8
• 化学式: C₁₅H₁₀OS
• mdl: MFCD11206880
• 分子量: 238.31
• InChiKey: YWKWBNMCWRUAMI-UHFFFAOYSA-N

物化性质

• 沸点：
  422.7±33.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  2
• 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：

  吡咯 、 5-(naphthalen-2-yl)thiophene-2-carbaldehyde 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以32%的产率得到meso-5,10,15,20-tetra(5-(2-naphthyl)thien-2yl)porphyrin
  参考文献：
  名称：

  Synthesis of meso-tetraarylthienylporphyrins by Suzuki-Miyaura cross-coupling reaction and studying their UV-Vis absorption spectra

  摘要：

  DOI：

  10.24820/ark.5550190.p011.292
• 作为产物：
  描述：

  2-噻吩甲醛 、 2-碘萘 在 1,10-菲罗啉 、 caesium carbonate 、 copper dichloride 作用下， 以 间二甲苯 为溶剂， 反应 24.0h， 以62%的产率得到5-(naphthalen-2-yl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  铜催化直接芳构化法用于染料敏化太阳能电池的D-π-A有机增敏剂的无锡和无钯合成

  摘要：

  Abstract<A variety of D–π–A‐type functional organic dyes are facilely synthesized by direct C−H arylation catalyzed by inexpensive copper salts. Under optimized reaction conditions, a broad substrate scope with good functional group compatibility was demonstrated. Based on this synthetic strategy, three new dye sensitizers (CYL‐5–7) were designed and fabricated for use in dye‐sensitized solar cells (DSSCs). Photovoltaic characterization showed that these devices gave open‐circuit voltages of 0.65–0.75 V, short‐circuit currents of 5.90–12.60 mA cm−2, and fill factors of 65.6–76.9 %, corresponding to power conversion efficiencies (PCEs) of 2.95–6.20 %. This work represents the first use of Cu‐catalyzed C−H arylation for a step‐saving, Sn‐free synthesis of precursor dyes for DSSC applications.

  DOI：

  10.1002/cssc.201700421

文献信息

• The 1,3-Diaminobenzene-Derived Aminophosphine Palladium Pincer Complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A Highly Active Suzuki-Miyaura Catalyst with Excellent Functional Group Tolerance
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/adsc.200900848

  日期：——

  The rapidly prepared 1,3‐diaminobenzene‐derived aminophosphine pincer complex C6H3[NHP(piperidinyl)2]2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side‐product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable

  快速制备的1,3-二氨基苯衍生的氨基膦钳形配合物C 6 H 3 [NHP（哌啶基）2 ] 2 Pd（Cl）}（1）是一种有效的Suzuki催化剂，具有出色的官能团耐受性。仅很少检测到副产物形成，例如均偶联，去溴化或原去硼，如果这样，在所有情况下均低于5％的水平。提出的反应方案是普遍适用的。实验观察表明，钯纳米颗粒的催化活性形式1。
• A metal-free cascade reaction of β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diols: synthesis of polycyclic 2-formylthiophenes
  作者：Limi Goswami、Kashmiri Neog、Kumud Sharma、Pranjal Gogoi

  DOI：10.1039/c7ob01641g

  日期：——

  A metal-free cascade reaction strategy has been developed for the synthesis of novel polycyclic 2-formylthiophenes from β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diol. Recyclable polymer supported organic base was used to perform the reaction process. This synthetic protocol was applied to synthesize several novel polycyclic thiophenes including steroidal D-ring annelated thiophene. Our

  已经开发了一种无金属级联反应策略，用于从β-卤代-α，β-不饱和醛和1,4-二噻吩-2,5-二醇合成新型多环2-甲酰基噻吩。使用可回收的聚合物负载的有机碱进行反应过程。该合成方案用于合成几种新型多环噻吩，包括甾体D环退火的噻吩。我们的合成策略可提供高产率的噻吩，避免繁琐的后处理程序并最大程度地减少废物的形成。
• Alkylidene pyrazolidinedione derivatives
  申请人：——

  公开号：US20040220188A1

  公开（公告）日：2004-11-04

  The present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) for the treatment and/or prevention of diabetes type I and/or II, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity and polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel alkylidene pyrazolidinedione derivatives. (I) R1 and R2 represent independently from each other an unsubstituted or substituted aryl or heteroaryl. 1

  本发明涉及使用式(I)的烷基亚甲基吡唑啉二酮衍生物治疗和/或预防糖尿病I型和/或II型、糖耐量受损、胰岛素抵抗、高血糖、肥胖症和多囊卵巢综合症（PCOS）。特别是，本发明涉及使用式(I)的烷基亚甲基吡唑啉二酮衍生物调节，特别是抑制PTPs的活性，尤其是PTP1B、TC-PTP、SHP和GLEPP-1的活性。本发明还涉及新的烷基亚甲基吡唑啉二酮衍生物。(I)中，R1和R2各自独立地表示未取代或取代的芳基或杂环芳基。
• Discovery of thiophen-2-ylmethylene bis-dimedone derivatives as novel WRN inhibitors for treating cancers with microsatellite instability
  作者：Hwasun Yang、Miso Kang、Seonyeong Jang、Soo Yeon Baek、Jiwon Kim、Gyeong Un Kim、Dongwoo Kim、Junsu Ha、Jong Seung Kim、Cheulhee Jung、Nam-Jung Kim、Sung-Yup Cho、Woong-Hee Shin、Juyong Lee、Junsu Ko、Ansoo Lee、Gyochang Keum、Sanghee Lee、Taek Kang

  DOI：10.1016/j.bmc.2024.117588

  日期：2024.2

  various cancer types. Recent research has identified Werner syndrome ATP-dependent helicase (WRN) as a promising synthetic lethal target for MSI cancers. Herein, we report the first discovery of thiophen-2-ylmethylene bis-dimedone derivatives as novel WRN inhibitors for MSI cancer therapy. Initial computational analysis and biological evaluation identified a new scaffold for a WRN inhibitor. Subsequent

  微卫星不稳定性 (MSI) 是一种由 DNA 错配修复系统缺陷引起的高突变状态，导致各种癌症类型的发展。最近的研究已确定维尔纳综合征 ATP 依赖性解旋酶 (WRN) 是 MSI 癌症的一个有前景的合成致死靶点。在此，我们报告了首次发现噻吩-2-基亚甲基双二甲酮衍生物作为用于 MSI 癌症治疗的新型 WRN 抑制剂。初步计算分析和生物学评估确定了 WRN 抑制剂的新支架。随后的 SAR 研究发现了一种高效的 WRN 抑制剂。此外，我们证明最佳化合物通过抑制 WRN 诱导 MSI 癌细胞 DNA 损伤和细胞凋亡。这项研究为 WRN 抑制剂提供了一种新的药效团，强调了它们对 MSI 癌症的治疗潜力。
• ALKYLIDENE PIRAZOLIDINEDIONE DERIVATIVES AND THEIR USE FOR TREATING DIABETES AND OBESITY
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1399156A2

  公开（公告）日：2004-03-24