2,6-ditert-butyl-4-[3-(2,6-ditert-butylselenopyran-1-ium-4-yl)prop-2-enylidene]selenopyran;chloride | 124620-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,6-ditert-butyl-4-[3-(2,6-ditert-butylselenopyran-1-ium-4-yl)prop-2-enylidene]selenopyran;chloride
• CAS: 124620-05-9
• 化学式: C₂₉H₄₃Se₂*Cl
• 分子量: 585.033
• InChiKey: HEWBASDBYPLNKD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-ditert-butyl-4-[3-(2,6-ditert-butylselenopyran-1-ium-4-yl)prop-2-enylidene]selenopyran;chloride 以 甲醇 、 水 为溶剂， 生成 2-(2,6-di-tert-butyl-4H-selenopyran-4-ylidene)acetaldehyde 、 2,6-Ditert-butyl-4-[3-(2,6-ditert-butylselenopyran-4-ylidene)-2-[(2,6-ditert-butylselenopyran-4-ylidene)methyl]propylidene]selenopyran 、 (E)-5-[(E)-3-(2,6-Di-tert-butyl-selenopyran-4-ylidene)-propenyl]-2,2,8,8-tetramethyl-non-4-ene-3,7-dione
  参考文献：
  名称：

  Hydrolysis Studies of Chalcogenopyrylium Trimethine Dyes. 2. Chalcogen Atom Effects on the Rates of Hydrolysis of Chalcogenopyrylium Dyes

  摘要：

  DOI：

  10.1021/jo980742z
• 作为产物：
  描述：

  2-(2,6-di-tert-butyl-4H-telluropyran-4-ylidene)acetaldehyde 、 2,6-di-tert-butyl-4-methyl-selenapyrylium chloride 在 乙酸酐 作用下， 反应 0.18h， 生成 2,6-ditert-butyl-4-[3-(2,6-ditert-butylselenopyran-1-ium-4-yl)prop-2-enylidene]selenopyran;chloride 、 2,6-Di-tert-butyl-4-[(E)-3-(2,6-di-tert-butyl-telluropyran-4-ylidene)-propenyl]-telluropyranylium; chloride 、
  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

文献信息

• 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.
• 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
• Chalcogenapyrylium dyes as photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting, and singlet-oxygen-induced inhibition of cytochrome c oxidase
  作者：Michael R. Detty、Paul B. Merkel、Russell Hilf、Scott L. Gibson、Stephen K. Powers

  DOI：10.1021/jm00166a005

  日期：1990.4

  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.