dibenzoselenophene oxide | 30467-70-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: dibenzoselenophene oxide
• 英文别名: dibenzoselenophene Se-oxide；dibenzo[b,d]selenophene 5-oxide；Dibenzoselenophene 5-oxide
• CAS: 30467-70-0
• 化学式: C₁₂H₈OSe
• 分子量: 247.155
• InChiKey: JYJFIATXHFONLG-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  dibenzoselenophene oxide 在 盐酸 、 硫酸 、 硝酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 2-Amino-dibenzo-selenophen
  参考文献：
  名称：

  3-Aminodibenzoselenophene and its derivatives

  摘要：

  DOI：

  10.1021/jo50014a008
• 作为产物：
  描述：

  2-氨基联苯 在 氢氧化钾 、 硫酸 、 溴 、 间氯过氧苯甲酸 、 sodium nitrite 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 dibenzoselenophene oxide
  参考文献：
  名称：

  Deoxygenation and Other Photochemical Reactions of Aromatic Selenoxides¹

  摘要：

  Atomic oxygen O(P-3) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical O((3)p) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene- oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O((3)p). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions.

  DOI：

  10.1021/ja045935k
• 作为试剂：
  描述：

  环己烯 在 dibenzoselenophene oxide 作用下， 以 二氯甲烷 为溶剂， 生成 氧化环己烯 、 2-环己烯醇
  参考文献：
  名称：

  Deoxygenation and Other Photochemical Reactions of Aromatic Selenoxides¹

  摘要：

  Atomic oxygen O(P-3) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical O((3)p) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene- oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O((3)p). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions.

  DOI：

  10.1021/ja045935k

文献信息

• GC: A Review of the State-of-the-Art Column Technologies for the Determination of ppm to ppb Levels of Oxygenated, Sulfur, and Hydrocarbon Impurities in C1-C5 Hydrocarbon Streams
  作者：J. de Zeeuw、C. Duvekot、J. Peene、P. Dijkwel、P. Heijnsdijk

  DOI：10.1093/chromsci/41.10.535

  日期：2003.11.1

  The determination of ppm to ppb levels of sulfur, oxygen-containing, and certain reactive hydrocarbons in bulk hydrocarbon feedstocks is important in the petroleum and petrochemical industry to minimize catalytic deactivation and improve product quality. Gas chromatography, coupled with selective or ultratrace universal detection (or both), is ideal in most cases for such analysis. However, to enhance

  在石油和石化工业中，测定散装烃原料中的硫，含氧和某些反应性烃的ppm到ppb的水平，对于最小化催化失活和提高产品质量至关重要。在大多数情况下，气相色谱与选择性或超痕量通用检测（或两者）结合是理想的分析方法。但是，为了提高痕量水平的选择性和定量分析，需要优化的固定相。这些相通常是吸附剂类型。本文总结了几种最先进的相用于分析痕量关键碳氢化合物，硫和氧化成分的性能。
• Visible light‐induced photodeoxygenation of polycyclic selenophene <i>Se</i> ‐oxides
  作者：Satyanarayana M. Chintala、John C. Throgmorton、Peter F. Maness、Ryan D. McCulla

  DOI：10.1002/poc.4144

  日期：2021.3

  2‐d]selenophene Se‐oxide, benzo[b]naphtho[2,1‐d]selenophene Se‐oxide, dinaphtho[2,3‐b:2’,3’‐d]selenophene Se‐oxide, and perylo[1,12‐b,c,d]selenophene Se‐oxide were synthesized, and their ability to utilize visible light for generating O(3P) was interrogated. Benzo[b]naphtho[1,2‐d]selenophene Se‐oxide produces O(3P) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2‐d]selenophene Se‐oxide, benzo[b]naphtho[2

  据信二苯并噻吩S-氧化物（DBTO）的光脱氧在溶液中产生基态原子氧[O（3 P）]。与其他活性氧（ROS）相比，O（3 P）具有强效和选择性，是一种独特的氧化剂。DBTO的衍生物已被用作O（3 P）的前体，以氧化多种分子，包括质粒DNA，蛋白质，脂质，硫醇和其他小有机分子。不幸的是，DBTO的光脱氧需要紫外线照射，这对于生物系统而言不是理想的波长范围，并且具有约0.003的低量子产率。在这项工作中，苯并[ b ]萘[1,2- d ]硒烯Se-氧化物，苯并[b ]萘并[2,1- d ]硒吩硒氧化物，二萘并[2,3- b：2' ，3'- d ]硒吩硒氧化物，和perylo [1,12- B，C，d ]硒吩合成了Se-氧化物，并研究了它们利用可见光生成O（3 P）的能力。苯并[ b ]萘[1,2- d ]硒烯Se-氧化物在420 nm处辐照会产生O（3 P）。此外，苯并[ b ]萘并[1,2- d
• VISIBLE LIGHT INDUCED PHOTOGENERATION OF GROUND STATE ATOMIC OXYGEN
  申请人：Saint Louis University

  公开号：US20200346183A1

  公开（公告）日：2020-11-05

  The present invention generally relates to various polycyclic aromatic selenoxide compounds, methods for preparing these compounds, and methods of us these and other compounds to generate ground state atomic oxygen.

  本发明通常涉及各种多环芳香硒氧化物化合物，制备这些化合物的方法，以及利用这些化合物和其他化合物生成基态原子氧的方法。
• Visible-light-catalyzed C–H arylation of (hetero)arenes <i>via</i> arylselenonium salts
  作者：Qiyue Wang、Xinyu Hao、Kun Jin、Rong Zhang、Chunying Duan、Yaming Li

  DOI：10.1039/d2ob00507g

  日期：——

  A novel photo-induced C–H arylation of (hetero)arenes has been developed. Aryl selenonium salts as an aryl source led to the arylation of aromatic (hetero)cyclic compounds via C–Se bond activation under blue LED irradiation. The method simply utilizes the safe and clean energy source and yields a range of site-selective biphenyl or bi-heterocyclic products in medium to good yields. Furthermore, the

  已经开发了一种新的光诱导的（杂）芳烃的 C-H 芳基化。芳基硒盐作为芳基源，在蓝色 LED 照射下通过C-Se 键活化导致芳族（杂）环化合物的芳基化。该方法简单地利用了安全和清洁的能源，并以中等至良好的收率产生了一系列位点选择性联苯或双杂环产品。此外，芳基硒盐的硼化和 Sonogashira 偶联也以良好的产率进行。结果表明，硒鎓盐比锍盐更具反应性。
• Molybdenum(<scp>v</scp>)-mediated switching of the C(sp²)–Se bond of phenylselenyl-functionalized arenes or heterocycles under mild conditions
  作者：Ming Zhang、Beifang Nian、Zhibang Wu、Jianhua Guo、Zhuo Chen、Caifeng Yuan、Xuankun Huang、Yiwen Shen、Hongbin Zhang、E. Tang

  DOI：10.1039/d3cc01119d

  日期：——

  phenylselenyl-functionalized arenes or heterocycles has been developed. Three kinds of benzoselenophene frameworks were constructed through this reaction with yields up to 94%. This new C(sp2)–Se bond-switching methodology may provide a new strategy for interesting applications of phenylselenyl-substituted aromatic compounds in the synthesis of selenium-containing heterocycles and natural products.

  钼( V )介导的C(sp 2 )–Se键和C(sp 2 )–H键断裂以及苯基硒基官能化芳烃或杂环的分子内氧化C(sp 2 )–Se偶联反应已被开发出来。通过该反应构建了三种苯并硒吩骨架，收率高达94%。这种新的C(sp 2 )–Se键转换方法可能为苯基硒基取代的芳香族化合物在含硒杂环和天然产物的合成中的有趣应用提供新的策略。,钼( V )介导的C(sp 2 )–Se键和C(sp 2 )–H键断裂以及苯基硒基官能化芳烃或杂环的分子内氧化C(sp 2 )–Se偶联反应已被开发出来。通过该反应构建了三种苯并硒吩骨架，收率高达94%。这种新的C(sp 2 )–Se键转换方法可能为苯基硒基取代的芳香族化合物在含硒杂环和天然产物的合成中的有趣应用提供新的策略。