6H,12H-dibenzo[b,f][1,5]diselenocin

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 6H,12H-dibenzo[b,f][1,5]diselenocin
• 英文别名: 6,12-Dihydrobenzo[c][1,5]benzodiselenocine
• 化学式: C₁₄H₁₂Se₂
• 分子量: 338.169
• InChiKey: OBIQTTJDOBBDPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  bis[2-(hydroxymethyl)phenyl] diselenide 在 氯化亚砜 作用下， 生成 6H,12H-dibenzo[b,f][1,5]diselenocin
  参考文献：
  名称：

  邻羟基甲基苯基硫属元素：合成，分子内非键硫属元素···OH相互作用和谷胱甘肽过氧化物酶样活性。

  摘要：

  描述了一系列衍生自苄醇13的有机硫属元素（Se，Te）化合物的合成和表征。的关键前体二硫属化物的合成15，22，和29被实现邻-lithiation路线。通过二锂化衍生物14与Se（dtc）2的反应获得硒化物18。用H 2 O 2氧化15和22分别得到相应的环状酯衍生物17和24。硒化物的氧化18与H 2 O 2一起提供螺环化合物19。通过单晶X射线研究已经证明了二杀菌剂15和22中分子内相互作用的存在。环状化合物17和19也已经通过单晶X射线研究表征。已通过偶联生物测定法评估了GP X样硒化合物的抗氧化活性。双碲化物22在mPW1PW91级别的密度泛函理论计算已经确定了羟基氧和碲原子之间相当强的非键相互作用。通过NBO分析获得的二阶摄动能传达了n O →σ* Te - Te轨道重叠在非键相互作用中的参与。使用分子原子（AIM）方法进行波后功能分析，确定了15和22中不同的键临界点，并且还

  DOI：

  10.1021/jo051309+

文献信息

• Deuterium-Induced Isotope Effects of a C–H···Se “Hydrogen Bond” on the IR and NMR Spectra of 6<i>H</i>,12<i>H</i>-Dibenzo[<i>b</i>,<i>f</i>][1,5]diselenocin
  作者：Michio Iwaoka、Hiroto Komatsu、Shuji Tomoda

  DOI：10.1246/bcsj.69.1825

  日期：1996.7

  Deuterium-induced isotope effects of the C–H···Se nonbonded interaction of 6H,12H-dibenzo[b,f][1,5]diselenocin (1) were investigated. The IR spectroscopic behavior of 6H,12H-dibenzo[b,f][1,5]diselenocin-6,6,12,12-d4 (1-d4) was compared with that of the reference compound (benzyl-α,α-d2 phenyl selenide (2-d2)). The results for both boat (1B) and chair (1C) conformers of 1 indicated that the C–H···Se interaction causes the decrease in the low wavenumber shift of ν1 (Δν1 = −2 cm−1 for 1B-d4 and −12 cm−1 for 1C-d4, whereas Δν1 = −15 cm−1 for 1B and −52 cm−1 for 1C). The 77Se NMR showed the upfield isotope shift due to the through-space C–H···Se interaction (ΔΔδ = 0.44 ppm for 1B and 0.25 ppm for 1C). These findings clearly suggested that the interaction is attractive in nature. MO calculations at the HF/3-21G* level and NBO analysis showed the importance of the electron delocalization from the selenium lone pair to the antibonding orbital of the C–H bond. These observations strongly suggested that the interaction be called a C–H···Se hydrogen bond.

  对6H,12H-二苯并[b,f][1,5]二硒杂环（1）的C-H……Se非键相互作用进行了氘诱导同位素效应研究。将6H,12H-二苯并[b,f][1,5]二硒杂环-6,6,12,12-d4（1-d4）的红外光谱行为与参考化合物（苄基-α,α-d2苯基硒化物（2-d2））的红外光谱行为进行了比较。1的船形（1B）和椅子形（1C）构象的结果表明，C-H……Se相互作用导致ν1的低波数位移减小（1B-d4的Δν1 = -2 cm-1，1C-d4的Δν1 = -12 cm-1，而1B的Δν1 = -15 cm-1，1C的Δν1 = -52 cm-1）。77Se NMR显示，由于空间贯穿的C-H……Se相互作用，出现了上向同位素位移（1B的ΔΔδ = 0.44 ppm，1C的ΔΔδ = 0.25 ppm）。这些发现清楚地表明，这种相互作用在本质上是有吸引力的。HF/3-21G*级别的
• Quantitative Evaluation of Weak Nonbonded Se···F Interactions and Their Remarkable Nature as Orbital Interactions
  作者：Michio Iwaoka、Hiroto Komatsu、Takayuki Katsuda、Shuji Tomoda

  DOI：10.1021/ja016348r

  日期：2002.3.1

  To evaluate weak intramolecular nonbonded Se...F interactions recently characterized for a series of o-selenobenzyl fluoride derivatives (Iwaoka et al., Chem. Lett. 1998, 969-970), the temperature dependence of the nuclear spin coupling between Se and F (J(Se...F)) was investigated for 2-(fluoromethyl)phenylselenenyl cyanate (1a) and bis[2-(fluoromethyl)phenyl] diselenide (le) in CD2Cl2 and CD3CN. A significant increase in the magnitude Of J(Se...F) was observed for both 1a and 1e upon lowering temperature, whereas the values Of J(Se...F) for the corresponding trifluoromethyl compounds slightly reduced or remained unchanged at low temperatures. Application of the rapid equilibrium model between two possible conformers revealed that conformer A with an intramolecular Se...F interaction is more stable in enthalpy (DeltaH by 1.23 kcal/mol for 1a (in CD2Cl2) and by 0.85 and 0.83 kcal/mol for le (in CD2Cl2 and CD3CN, respectively) than conformer B, which does not have close Se...F contact. The negligible solvent effects for 1e suggested marginal electrostatic nature of the Se...F interactions. Instead, importance of the n(F) --> sigma*(Se-x) orbital interaction was suggested by quantum chemical (QC) calculations and the natural bond orbital (NBO) analysis.