4-(Methylseleno)-1-decene | 61540-01-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(Methylseleno)-1-decene
• 英文别名: 4-methylseleno-1-decene；4-methylselanyl-dec-1-ene；1-Decene, 4-(methylseleno)-；4-methylselanyldec-1-ene
• CAS: 61540-01-0
• 化学式: C₁₁H₂₂Se
• 分子量: 233.256
• InChiKey: WOEKYMZWQFXFJB-UHFFFAOYSA-N

物化性质

• 沸点：
  253.1±19.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  4-(Methylseleno)-1-decene 、 叔丁基过氧化氢 、 蓝宝石粉 、 四氢呋喃 以90%的产率得到
  参考文献：
  名称：

  CLAREMBEAU, M.;BERTRAND, J. L.;KRIEF, A., ISRAEL J. CHEM., 1984, 24, N 2, 125-133

  摘要：

  DOI：
• 作为产物：
  描述：

  庚醛二甲基缩醛 在 三氟化硼乙醚 、 三溴化硼 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-(Methylseleno)-1-decene
  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

• Reduction or alkylative reduction of the carbonyl group
  作者：M. Sevrin、D. Van Ende、A. Krief

  DOI：10.1016/s0040-4039(00)91757-x

  日期：1976.7
• Hermans, Bernard; Hevesi, Laszlo, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 5-6, p. 257 - 262
  作者：Hermans, Bernard、Hevesi, Laszlo

  DOI：——

  日期：——
• The reaction of allyltrimethylsilane with selenium-stabilized carbon electrophiles
  作者：Bernard Hermans、Laszlo Hevesi

  DOI：10.1016/s0040-4039(00)97623-8

  日期：1990.1
• HERMANS, BERNARD;HEVESI, LASZLO, TETRAHEDRON LETT., 31,(1990) N0, C. 4363-4366
  作者：HERMANS, BERNARD、HEVESI, LASZLO

  DOI：——

  日期：——
• 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.