1,2-propadienyl benzyl selenide | 847549-62-6

• 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: 1,2-propadienyl benzyl selenide
• 英文别名: 1-benzylselanylpropadiene
• CAS: 847549-62-6
• 化学式: C₁₀H₁₀Se
• 分子量: 209.149
• InChiKey: SOQXTBONNBMABN-UHFFFAOYSA-N

物化性质

• 沸点：
  286.0±23.0 °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：
  0.1
• 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：

  1,2-propadienyl benzyl selenide 在 水 、 碘 作用下， 以 乙腈 为溶剂， 反应 11.5h， 以58%的产率得到(Z)-3-(benzylseleno)-2-iodo-2-propen-1-ol
  参考文献：
  名称：

  Studies on the Regio- and Stereoselectivity of Halohydroxylation of 1,2-Allenyl Sulfides or Selenides

  摘要：

  It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br-2 (CuBr2 or NBS) or I-2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom was halohydroxylated with the halogen atom connecting to the middle carbon atom and the hydroxyl group connecting to the non-S terminal carbon or Se-substituted terminal carbon atom of the allene moiety), leading to the synthesis of synthetically important 3-organosulfur or seleno-2-haloallylic alcohols. The stereoselectivity depends on the nature of X+ and S or Se, showing a Z-selectivity with the matched Lewis acid-base pair.

  DOI：

  10.1021/jo049593c
• 作为产物：
  描述：

  benzyl prop-2-yn-1-yl selenide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 以60%的产率得到1,2-propadienyl benzyl selenide
  参考文献：
  名称：

  Studies on the Regio- and Stereoselectivity of Halohydroxylation of 1,2-Allenyl Sulfides or Selenides

  摘要：

  It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br-2 (CuBr2 or NBS) or I-2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom was halohydroxylated with the halogen atom connecting to the middle carbon atom and the hydroxyl group connecting to the non-S terminal carbon or Se-substituted terminal carbon atom of the allene moiety), leading to the synthesis of synthetically important 3-organosulfur or seleno-2-haloallylic alcohols. The stereoselectivity depends on the nature of X+ and S or Se, showing a Z-selectivity with the matched Lewis acid-base pair.

  DOI：

  10.1021/jo049593c

文献信息

• Stereoselective Z-iodoalkoxylation of 1,2-allenyl sulfides or selenides
  作者：Chunling Fu、Guofei Chen、Xiaoyi Liu、Shengming Ma

  DOI：10.1016/j.tet.2005.05.077

  日期：2005.8

  Iodoalkylation of 1,2-allenyl sulfides or selenides with 1(2) in MeCN/ROH (20: 1) afforded Z-3-alkoxy-2-iodopropeny) sulfides or selenides in high stereoselectivity and moderate to Pod yields. The carbon-iodine bonds in these compounds may undergo Suzuki, Negishi, and Sonogashira coupling reaction smoothly. (c) 2005 Elsevier Ltd. All rights reserved.
• Specific features of the reactions of 2,3-dichloro-1-propene with dibenzylchalcogenides in the system hydrazine hydrate-alkali
  作者：E. P. Levanova、V. A. Grabel’nykh、V. S. Vakhrina、N. V. Russavskaya、A. I. Albanov、I. B. Rozentsveig、N. A. Korchevin

  DOI：10.1134/s1070363214030050

  日期：2014.3

  Dibenzyldisulfide and -diselenide react with 2,3-dichloro-1-propene in the system hydrazine hydrate-KOH by the domino mechanism: nucleophilic substitution of the allyl chlorine, dehydrochlorination with participation of the chlorine atom at the sp (2)-carbon atom, allene-acetylene rearrangement, nucleophilic addition of the chalcogenide reagent to the triple bond. The effect of the nature of the chalcogen atom and the benzyl substituent on the studied domino reaction is discussed.