(Methoxy-methylselanyl-methyl)-benzene | 153992-06-4

• 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: (Methoxy-methylselanyl-methyl)-benzene
• 英文别名: [Methoxy(methylselanyl)methyl]benzene
• CAS: 153992-06-4
• 化学式: C₉H₁₂OSe
• 分子量: 215.154
• InChiKey: MLRKLUUJOZAGPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Methoxy-methylselanyl-methyl)-benzene 在 (6-氨基己基氨基)甲基-(二乙氧基甲基)硅 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 Triethyl-(1-methoxy-1-phenyl-hex-5-enyl)-silane
  参考文献：
  名称：

  ω-Alkenyl-α-Methoxy-Benzyllithiums : Original Synthesis and Reactivity

  摘要：

  1-Methoxy-benzyllithiums bearing suitably positioned C,C double bonds possess a high propensity to produce a five or a six membered cycle by carbocyclisation reaction. The reaction proceeds completely stereoselectively and produces a five membered cycle possessing the cis-stereochemistry between the methoxy and the adjacent methyl group. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01411-1
• 作为产物：
  描述：

  甲基硒基 、 苯甲醛二甲缩醛 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以56%的产率得到(Methoxy-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

• α-Methoxy-Benzylmetals : Original Synthesis and Reactivity
  作者：Alain Krief、Jamal Bousbaa

  DOI：10.1016/s0040-4039(97)01410-x

  日期：1997.9

  Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing l-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF3-OEt2 to produce the homologated tetrahydropyran derivative in good yield. (C) 1997 Published by Elsevier Science Ltd.
• Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane
  作者：Bernard Hermans、Laszlo Hevesi

  DOI：10.1021/jo00124a029

  日期：1995.9

  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.
• ω-Alkenyl-α-Methoxy-Benzyllithiums : Original Synthesis and Reactivity
  作者：Alain Krief、Jamal Bousbaa

  DOI：10.1016/s0040-4039(97)01411-1

  日期：1997.9

  1-Methoxy-benzyllithiums bearing suitably positioned C,C double bonds possess a high propensity to produce a five or a six membered cycle by carbocyclisation reaction. The reaction proceeds completely stereoselectively and produces a five membered cycle possessing the cis-stereochemistry between the methoxy and the adjacent methyl group. (C) 1997 Published by Elsevier Science Ltd.