benzyl methyl selenide | 5925-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl methyl selenide
• 英文别名: Benzene, [(methylseleno)methyl]-；methylselanylmethylbenzene
• CAS: 5925-78-0
• 化学式: C₈H₁₀Se
• 分子量: 185.127
• InChiKey: HBOLIXMCOJOFIK-UHFFFAOYSA-N

物化性质

• 沸点：
  64 °C(Press: 0.6 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  benzyl methyl selenide 在 sodium amide 作用下， 以 氨 为溶剂， 生成 2-methylbenzyl methyl selenide
  参考文献：
  名称：

  苄基硒鎓盐的碱处理。[2,3]亲核重排与亲核取代

  摘要：

  用各种碱某些苄基硒鎓盐的治疗导致在亲核攻击，以产生烷基化或基座的苄基化，而在液氨中使用氨基钠作为碱生成由此获得硒叶立德邻苄基的取代通过[2,3]σ重排。

  DOI：

  10.1039/c39800000558
• 作为产物：
  描述：

  硒氰酸苄酯 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.25h， 生成 benzyl methyl selenide
  参考文献：
  名称：

  Experimental and Theoretical Studies on the Nature of Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms

  摘要：

  To investigate the nature of weak nonbonded selenium(...)halogen interactions ((SeX)-X-... interactions; X = F Cl, and Br), three types of model compounds [2-(CH2X)C6H4SeY (1-3), 3-(CH2X)-2-C10H6-SeY (4-6), and 2-XC6H4CH2SeY (7-9); Y = CN, Cl, Br, SeAr, and Me] were synthesized, and their Se-77 NMR spectroscopic behaviors were analyzed in CDCl3. The gradual upfield shifts of Se-77 NMR absorptions observed for series 1-3 and 4-6 suggested that the strength of (SeX)-X-... interaction decreases in the order of (SeF)-F-... > (SeCl)-Cl-... > (SeBr)-Br-.... The quantum chemical calculations at the B3LYP/631H level using the polarizable continuum model (PCM) revealed that the most stable conformer for 1-3 is the one with an intramolecular short (SeX)-X-... atomic contact in CHCl3 (epsilon = 4.9) and also that the n(x) --> sigma*(se-y) orbital interaction (E-Se...X) can reasonably explain the order of strength for the (SeX)-X-... interactions. On the other hand, the Se-77 NMR absorptions observed for series 7-9 did not shift significantly from the reference compounds (C6H5CH2SeY), indicating the absence of the (SeX)-X-... interaction for 7-9 presumably due to attenuation of basicity for the halogen atom that is substituted directly to the aromatic ring. These observations suggested that the n(x) --> sigma*(se-y) orbital interaction is a dominant factor for formation of weak (SeX)-X-... interactions. Electron correlation was also suggested to be important for the stability.

  DOI：

  10.1021/jo048436a

文献信息

• Novel synthesis of tertiary alkyl, secondary and tertiary benzyl, and allyl selenides from the corresponding alcohols
  作者：M. Clarembeau、A. Krief

  DOI：10.1016/s0040-4039(01)91092-5

  日期：1984.1

  We report an efficient synthesis of the title compounds from alcohols and selenols. The scope and limitations of the new method are disclosed.

  我们报告了从醇和硒醇的标题化合物的有效合成。公开了新方法的范围和局限性。
• Reduction vs. acetalisation of some carbonyl compounds by means of methylselenol and Lewis acids
  作者：Alfredo Cravador、Alain Krief、L�szl� Hevesi

  DOI：10.1039/c39800000451

  日期：——

  Aliphatic ketones and aromatic carbonyl compounds on reaction with methylselenol and a Lewis acid, are shown to undergo acetalisation and/or reduction to methyl selenide, the unexpected reduction reaction being predominant in most cases.

  与甲基硒醇和路易斯酸反应后，脂族酮和芳族羰基化合物被缩醛化和/或还原成亚硒酸甲酯，在大多数情况下，意想不到的还原反应占主导。
• FeCl₃-Diorganyl Dichalcogenides Promoted Cyclization of 2-Alkynylanisoles to 3-Chalcogen Benzo[<i>b</i>]furans
  作者：Rafaela M. Gay、Flávia Manarin、Caroline C. Schneider、Daniela A. Barancelli、Michael D. Costa、Gilson Zeni

  DOI：10.1021/jo101126q

  日期：2010.8.20

  2-alkynylanisoles, via FeCl3/diorganyl dichalcogenides intramolecular cyclization, has been developed. Aryl and alkyl groups directly bonded to the chalcogen atom were used as cycling agents. The results revealed that the reaction significantly depends on the electronic effects of substituents in the aromatic ring bonded to the selenium atom of the diselenide species. We observed that the pathway of reaction was

  通过FeCl 3从容易获得的2-炔基苯甲醚中合成3-硫属元素苯并[ b ]呋喃/ diorganyl dichalcogenides分子内环化已得到开发。直接结合到硫属元素原子上的芳基和烷基用作循环剂。结果表明，该反应显着取决于与二硒化物物种的硒原子键合的芳环中取代基的电子效应。我们观察到反应途径对苯甲醚芳环中取代基的性质不敏感，因为给电子基团和吸电子基团均以相似的产率传递产物。此外，将得到的杂环被容易地通过使用与硫属/锂交换反应转化成更复杂的产品Ñ-BuLi，然后用醛截留锂中间体，以良好的产率提供所需的仲醇。
• Novel synthesis of benzyllithiums from benzylselenides
  作者：M. Clarembeau、A. Krief

  DOI：10.1016/s0040-4039(00)98521-6

  日期：1985.1

  Benzylselenides are found to be valuable precursors of benzyllithiums. The scope of the new method is disclosed.

  发现苄基硒化物是苄基锂的有价值的前体。公开了新方法的范围。
• Convenient Transformation of Benzyl Alcohol into Its Corresponding Selenide Using the Selenolate Anion-Aluminum Chloride Combination System.
  作者：Hitoshi ABE、Akira YAMASAKI、Hiroyuki FUJII、Takashi HARAYAMA

  DOI：10.1248/cpb.44.2223

  日期：——

  Treatment of benzyl alcohol with a new reagent system, benzene- or methaneselenolate anion-aluminum chloride, yielded the corresponding selenide. The one-pot conversion of benzaldehyde into benzyl selenide was also achieved by this system.

  用新的试剂系统苯-或甲硒酸盐阴离子-氯化铝处理苯甲醇，产生相应的硒化物。该系统还实现了苯甲醛一锅法转化为硒化苄。