2-(2,6-di-tert-butyl-4H-telluropyran-4-ylidene)acetaldehyde | 103817-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,6-di-tert-butyl-4H-telluropyran-4-ylidene)acetaldehyde
• 英文别名: (2,6-Di-tert-butyl-telluropyran-4-ylidene)-acetaldehyde；2-(2,6-Ditert-butyltelluropyran-4-ylidene)acetaldehyde
• CAS: 103817-95-4
• 化学式: C₁₅H₂₂OTe
• 分子量: 345.939
• InChiKey: SJKNRNCJJFOPOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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-(2,6-di-tert-butyl-4H-telluropyran-4-ylidene)acetaldehyde 在 溴 、 乙酸酐 、 sodium hydrogensulfite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.26h， 生成
  参考文献：
  名称：

  Chalcogenapyrylium dyes as photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting, and singlet-oxygen-induced inhibition of cytochrome c oxidase

  摘要：

  Cationic selena- and tellurapyrylium dyes 1d-g and 1i were found to inhibit cytochrome c oxidase upon irradiation of isolated mitochondrial suspensions treated with 10 microM solutions of dye. The amount of inhibition by these dyes was found to be related to oxygen concentration and inversely related to the concentration of added imidazole, a singlet-oxygen trap, suggesting that singlet oxygen is responsible, at least in part, for the inhibition of the enzyme. Dyes 1d-g and 1i, containing either selenium or tellurium, produce singlet oxygen with a quantum efficiency, phi (1O2), between 0.005 and 0.09 in methanol. Dyes 1a-c, containing the lighter chalcogens oxygen and sulfur, have values of phi (1O2) that are less than 0.0008 in methanol and do not inhibit cytochrome c oxidase in irradiated mitochondrial suspensions. Dyes 1c and 1d have nearly identical spectral and redox properties. Only the selenapyrylium dye 1d inhibits the enzyme, suggesting that neither ground-state nor excited-state electron transfer is important in inhibition of the enzyme. Electron micrographs of human U251 glioma cells, treated in vitro with 1i and light, showed pronounced morphology changes in the mitochondrial membranes relative to electron micrographs of untreated cells. Epifluorescence microscopy of the treated cells showed granular yellow-green fluorescence presumably from photooxidized dye in the mitochondria.

  DOI：

  10.1021/jm00166a005
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以54%的产率得到2-(2,6-di-tert-butyl-4H-telluropyran-4-ylidene)acetaldehyde
  参考文献：
  名称：

  揭示硫属鎓聚甲炔染料的溶液和激发态动力学

  摘要：

  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

  DOI：

  10.1021/acs.organomet.2c00263

文献信息

• Tellurapyrylium dyes as catalysts for the conversion of singlet oxygen and water to hydrogen peroxide
  作者：Michael R. Detty、Scott L. Gibson

  DOI：10.1021/ja00166a083

  日期：1990.5

  for light-to-chemical energy conversion is important for application to solar-energy storage schemes. While the major emphasis in such research has been water splitting for the production of hydrogen, the photoproduction of other energy-rich compounds such as hydrogen peroxide has also received attention. The authors report novel, catalytic reactions of tellurapyrlium dye 1 that utilize tellurium(IV)

  光化学能转换方法的开发对于太阳能存储方案的应用非常重要。虽然此类研究的主要重点是用于生产氢气的水分解，但其他富含能量的化合物（如过氧化氢）的光生产也受到了关注。作者报告了利用碲 (IV) 物质 2 作为中间体的碲吡咯染料 1 的新型催化反应。
• Hydrolysis Studies of Chalcogenopyrylium Trimethine Dyes. 1. Product Studies in Alkaline Solution (pH ≥ 8) under Anaerobic and Aerobic Conditions
  作者：David N. Young、Michael R. Detty

  DOI：10.1021/jo970115u

  日期：1997.7.1

  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.
• 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
• Detty, Michael R.; Merkel, Paul B., Journal of the American Chemical Society, 1990, vol. 112, # 10, p. 3845 - 3855
  作者：Detty, Michael R.、Merkel, Paul B.

  DOI：——

  日期：——
• Hydrolysis Studies of Chalcogenopyrylium Trimethine Dyes. 2. Chalcogen Atom Effects on the Rates of Hydrolysis of Chalcogenopyrylium Dyes
  作者：David N. Young、Petr Serguievski、Michael R. Detty

  DOI：10.1021/jo980742z

  日期：1998.8.1