2,6-di-tert-butyl-4H-telluropyran-4-one | 86029-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 2,6-di-tert-butyl-4H-telluropyran-4-one
• 英文别名: 2,6-Ditert-butyltelluropyran-4-one
• CAS: 86029-92-7
• 化学式: C₁₃H₂₀OTe
• 分子量: 319.901
• InChiKey: DNLHVRLULZGUDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-di-tert-butyl-4H-telluropyran-4-one 在 溴 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到1,1-Dibromo-2,6-di-tert-butyl-1H-1λ⁴-telluropyran-4-one
  参考文献：
  名称：

  Electron-accepting molecules containing telluropyranyl groups. The effect of tellurium oxidation state on reduction potentials

  摘要：

  DOI：

  10.1021/jo00387a002
• 作为产物：
  描述：

  2,6-di-tert-butyl-4-methyltellurinium hexafluorophosphate 在 dipotassium hydrogenphosphate 、 air 作用下， 以 乙腈 为溶剂， 以22%的产率得到2,6-di-tert-butyl-4H-telluropyran-4-one
  参考文献：
  名称：

  Hydrolysis Studies of Chalcogenopyrylium Trimethine Dyes. 1. Product Studies in Alkaline Solution (pH ≥ 8) under Anaerobic and Aerobic Conditions

  摘要：

  Hydrolyses of chalcogenopyrylium dyes 1-9 give product distributions that are both heteroatom and oxygen dependent, Under anaerobic or aerobic conditions at pH 8, hydrolyses of dyes 1-4, which each contain a pyrylium ring, give 2-pentene-1,5-dione 10-13, respectively, in >90% yield from addition of hydroxide to the 2-position of the pyrylium ring followed by ring opening and tautomerization. Telluropyrylium dye 8 under anaerobic conditions over the pH range 6.9-11.0 gives a 1:1 mixture of telluropyranylidene aldehyde 14 and tris(telluropyranylidenemethyl)methane 15 derived from addition of hydroxide to the central carbon of the trimethine bridge. Under aerobic conditions, tellurophene 30(Te,Te) and trace amounts of telluropyranone 29 were also produced via oxidative mechanisms with relative yields of 30(Te,Te) increasing with pH over the pH range 6.9-11.0 and with oxygen concentration. Thiopyrylium dye 9, seleno-/thiopyrylium dye 5, selenopyrylium dye 6, and seleno-/telluropyrylium dye 7 gave hydrolysis products derived from addition of hydroxide to the 2-position of the selenopyrylium ring (thiopyrylium ring for 9) as well as to the central carbon of the trimethine backbone under both anaerobic and aerobic conditions. The resulting seleno- or thio-hemiketals ring-opened to the corresponding seleno ketones, which were then hydrolyzed to the 2-pentene-1,5-diones 11-13 from 5-7, respectively, and 11 from 9. Under aerobic conditions, some oxidation of the seleno-hemiketals from 5 and 6 were observed to give selenophenes 30(Se,S) and 30(SeSe), respectively, as well as oxidation of the telluro-hemiketal from 9 and 8 to give tellurophenes 30(Te,Se) and 30(Te,Te), repectively. Chalcogenopyranones 27-29 were also produced in modest yields in the aerobic reactions.

  DOI：

  10.1021/jo970115u

文献信息

• Chalcogenopyranones from disodium chalcogenide additions to 1,4-pentadiyn-3-ones. The role of enol ethers as intermediates
  作者：Kristi Leonard、Marina Nelen、Madhavi Raghu、Michael R. Detty

  DOI：10.1002/jhet.5570360322

  日期：1999.5

  chalcogenides to give mixtures of products in which the chalcogenopyranones 1 are minor components and the dihydrochalcogenophenes 3 are the major products. The addition of hydrogen sulfide to diynone 2b in ethanol gives a product mixture nearly identical to that observed for the addition of disodium sulfide in sodium ethoxide in ethanol to 2b. Intermediates for the addition of hydrogen chalcogenides and

  通过在乙醇钠/乙醇中将乙醇加成到1，4-戊二炔-3-酮2中，形成E-和Z-异构体的混合物的烯醇醚9。烯醇醚与硫属元素化物二钠反应，以高收率得到相应的带有烷基，芳基或杂芳基取代基的2，6-二取代硫属元素吡喃酮类化合物1，这是反应的唯一杂环产物。二炔酮2与硫属元素化物二钠反应，得到产物混合物，其中硫属元素合吡喃酮类1是次要成分，而二氢硫属元素芴3是主要产物。向二酮2b中添加硫化氢乙醇中的产物混合物与乙醇中乙醇钠中的硫化钠硫化钠加至2b中观察到的几乎相同。描述了用于向2和9二者中添加硫属元素氢和硫属元素二钠的中间体，其导致杂环产物。
• Chalcogenopyrylium Dyes as Differential Modulators of Organic Anion Transport by Multidrug Resistance Protein 1 (MRP1), MRP2, and MRP4
  作者：Robert L. Myette、Gwenaëlle Conseil、Sean P. Ebert、Bryan Wetzel、Michael R. Detty、Susan P. C. Cole

  DOI：10.1124/dmd.112.050831

  日期：2013.6

  Multidrug resistance proteins (MRPs) mediate the ATP-dependent efflux of structurally diverse compounds, including anticancer drugs and physiologic organic anions. Five classes of chalcogenopyrylium dyes (CGPs) were examined for their ability to modulate transport of [3H]estradiol glucuronide (E217 β G; a prototypical MRP substrate) into MRP-enriched inside-out membrane vesicles. Additionally, some CGPs were tested in intact transfected cells using a calcein efflux assay. Sixteen of 34 CGPs inhibited MRP1-mediated E217 β G uptake by >50% (IC50 values: 0.7–7.6 µ M). Of 9 CGPs with IC50 values ≤2 µ M, two belonged to class I, two to class III, and five to class V. When tested in the intact cells, only 4 of 16 CGPs (at 10 µ M) inhibited MRP1-mediated calcein efflux by >50% (III-1, V-3, V-4, V-6), whereas a fifth (I-5) inhibited efflux by just 23%. These five CGPs also inhibited [3H]E217 β G uptake by MRP4. In contrast, their effects on MRP2 varied, with two (V-4, V-6) inhibiting E217 β G transport (IC50 values: 2.0 and 9.2 µ M) and two (V-3, III-1) stimulating transport (>2-fold), whereas CGP I-5 had no effect. Strikingly, although V-3 and V-4 had opposite effects on MRP2 activity, they are structurally identical except for their chalcogen atom (Se versus Te). This study is the first to identify class V CGPs, with their distinctive methine or trimethine linkage between two disubstituted pyrylium moieties, as a particularly potent class of MRP modulators, and to show that, within this core structure, differences in the electronegativity associated with a chalcogen atom can be the sole determinant of whether a compound will stimulate or inhibit MRP2.

  多药耐药蛋白（MRPs）介导结构多样化化合物（包括抗癌药物和生理有机阴离子）的ATP依赖性外排。研究了五类硫族吡啶染料（CGPs）对[3H]雌二醇葡萄糖苷（E217 β G；一种典型的MRP底物）进入富含MRP的内侧外翻膜囊泡的调节能力。此外，某些CGPs在完整的转染细胞中使用钙黄绿素外排测定进行了测试。在34种CGPs中，有16种抑制了MRP1介导的E217 β G摄取超过50%（IC50值：0.7–7.6 µM）。在9种IC50值≤2 µM的CGPs中，两个属于I类，两个属于III类，五个属于V类。在完整细胞测试中，仅有16种CGPs中的4种（在10 µM浓度下）抑制了MRP1介导的钙黄绿素外排超过50%（III-1, V-3, V-4, V-6），而第五种（I-5）仅抑制了23%。这五种CGPs还抑制了MRP4对[3H]E217 β G的摄取。相较之下，它们对MRP2的影响各不相同，其中两种（V-4, V-6）抑制了E217 β G的运输（IC50值：2.0和9.2 µM），两种（V-3, III-1）则刺激了运输（>2倍），而CGP I-5没有任何影响。值得注意的是，尽管V-3和V-4对MRP2活性的影响相反，但它们的结构除了硫族原子（Se与Te）外是完全相同的。本研究首次识别了V类CGPs，它们具有独特的亚甲基或三亚甲基连接两个双取代吡啶基团，作为特别有效的MRP调节剂，并表明在这一核心结构内，与硫族原子相关的电负性差异可以是决定化合物是刺激还是抑制MRP2的唯一因素。
• Shining Light on the Solution- and Excited-State Dynamics of Chalcogenopyrylium Polymethine Dyes
  作者：Lauren E. Rosch、Matthew R. Crawley、Ryan M. O’Donnell、Thomas N. Rohrabaugh、Trenton R. Ensley、Thomas A. Sobiech、Timothy R. Cook

  DOI：10.1021/acs.organomet.2c00263

  日期：2022.8.22

  singlet oxygen yields as high as 12% for certain dyes, we observe no evidence for 1O2 from direct phosphorescence measurements. We now fill in many of these gaps through steady-state and pulsed-laser kinetic experiments on a family of 14 dyes, including six novel dyes, selected to vary physical and electronic structure. These structural changes encompass the selenium and tellurium heteroatoms, phenyl,

  尽管 40 年来人们对硫属吡喃多甲炔染料感兴趣，但我们对其光物理特性的理解仍存在重大差距。这些差距阻碍了将这些染料应用为光动力疗法和/或生物医学传感剂的努力，其中完全了解它们的激发态动力学和化学是很重要的。例如，尽管先前的报道确定某些染料的单线态氧产量高达 12%，但我们没有观察到1 O 2的证据来自直接磷光测量。我们现在通过对 14 种染料家族（包括六种新型染料）进行稳态和脉冲激光动力学实验来填补这些空白，这些染料被选为改变物理和电子结构。这些结构变化包括硒和碲杂原子、苯基、噻吩、叔-丁基取代基和次甲基接头长度。通过飞秒瞬态吸收光谱获得激发态寿命。寿命都低于 300 ps，这表明它们的激发态会快速弛豫。值得注意的是，我们没有观察到任何三重态瞬态过程的证据。磷光仅在 77 K 的样品中观察到。变温 NMR 实验表明，吡喃环围绕次甲基骨架的旋转是这些染料动力学的关键决定因素，从而将它们的光物
• A Mechanism for Heteroatom Scrambling in the Synthesis of Unsymmetrical Chalcogenopyrylium Trimethine Dyes
  作者：Michael R. Detty、David N. Young、Antony J. Williams

  DOI：10.1021/jo00125a066

  日期：1995.10
• Δ4,4' -4-chalcogenapyranyl-4h-chalcogenapyrans
  作者：Michael R. Detty、James W. Hassett、Bruce J. Murray、George A. Reynolds

  DOI：10.1016/s0040-4020(01)96724-9

  日期：1985.1