(Bis-methylselanyl-methyl)-benzene | 94417-52-4

• 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: (Bis-methylselanyl-methyl)-benzene
• 英文别名: Bis(methylselanyl)methylbenzene
• CAS: 94417-52-4
• 化学式: C₉H₁₂Se₂
• 分子量: 278.114
• InChiKey: IDHJIZAVPLGYFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  309.4±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (Bis-methylselanyl-methyl)-benzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (1-丁基庚基)-苯
  参考文献：
  名称：

  芳族醛和酮羰基双二烷基化的新方法

  摘要：

  通过使用硒方法可以有效地实现标题转化，该方法涉及芳基硒缩醛和苄基硒化物的顺序还原烷基化。

  DOI：

  10.1016/s0040-4039(00)84356-7
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 三氯化铝 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Bis-methylselanyl-methyl)-benzene
  参考文献：
  名称：

  Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

  摘要：

  On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides. This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated; or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used. In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of(O,S) mixed acetals are-interpreted in terms of two major factors operating in opposite directions. H-1 NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed. However, because of the much stronger C-O bond as compared to the C-Se bond, this latter.(also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products. In contrast with BF3 . OEt(2), boron trichloride and boron tribromide were found to react with (O,Se) acetals to give the corresponding alpha-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

  DOI：

  10.1021/jo00124a029

文献信息

• C/se bond cleavage of functionalized selenides by lithium arenides : Application to the geminal di-allylation of the carbonyl group of aldehydes and ketones.
  作者：Alain Krief、Abdesslame Nazih

  DOI：10.1016/0040-4039(95)01690-j

  日期：1995.10

  lithium selenolates, α-selenoalkyllithiums or α-alkoxyalkyllithiums respectively. We took advantage of these reactions as well as of the ones involving the synthesis of atkyllithiums from selenides to propose an original method for geminal di-allylation of the carbonyl group of aldehydes and ketones.

  硒缩醛以及混合的（O，Se）缩醛与砷化锂反应，除亚硒酸锂外，还分别生成α-硒代烷基锂或α-烷氧基烷基锂。我们利用这些反应以及涉及从硒化物合成烷基锂的反应，提出了一种用于醛和酮的羰基双双烯丙基化的原始方法。
• Cleavage of selenoacetals by clay-supported metal nitrates
  作者：Pierre Laszlo、Pascal Pennetreau、Alain Krief

  DOI：10.1016/s0040-4039(00)84740-1

  日期：——

  Bis(methylseleno)acetals and bis(phenylseleno)acetals are cleaved into aldehydes or ketones, under very mild conditions, by K10 clay-supported ferric or cupric nitrate.

  双（甲基硒代）缩醛和双（苯基硒代）缩醛在非常温和的条件下，被K10粘土负载的硝酸铁或硝酸铜裂解为醛或酮。
• Synthesis of arylcycloalkanes from ω-alkenyl benzylselenides
  作者：Alain Krief、Benoit Kenda、Phillipe Barbeaux、Eric Guittet

  DOI：10.1016/s0040-4020(01)85242-x

  日期：1994.1

  Arylcycloalkanes are produced from ω-alkenyl benzylselenides on reaction with alkyllithiums or on Lewis acid mediated electrophilic cyclisation.

  芳基环烷烃是由ω-烯基苄基硒化物在与烷基锂反应或路易斯酸介导的亲电环化反应中产生的。
• Synthesis of selenoacetals
  作者：M. Clarembeau、A. Cravador、W. Dumont、L. Hevesi、A. Krief、J. Lucchetti、D. Van Ende

  DOI：10.1016/s0040-4020(01)96719-5

  日期：1985.1
• Metallation of benzyl selenides and of α-aryl selenoacetals. Scope and limitations.
  作者：M. Clarembeau、A. Krief

  DOI：10.1016/s0040-4039(00)84357-9

  日期：1986.1