2-(2,6-di-tert-butyl-4H-selenopyran-4-ylidene)acetaldehyde | 103817-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-(2,6-di-tert-butyl-4H-selenopyran-4-ylidene)acetaldehyde
• 英文别名: (2,6-Di-tert-butyl-selenopyran-4-ylidene)-acetaldehyde；2-(2,6-Ditert-butylselenopyran-4-ylidene)acetaldehyde
• CAS: 103817-96-5
• 化学式: C₁₅H₂₂OSe
• 分子量: 297.299
• InChiKey: YVZCODJNZMHBSY-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±42.0 °C(Predicted)

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-selenopyran-4-ylidene)acetaldehyde 在 双氧水 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以79%的产率得到2-(2,6-di-tert-butyl-4H-selenopyran-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

• 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