1,2-propadienyl p-tolyl selenide | 613688-18-9

• 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 p-tolyl selenide
• CAS: 613688-18-9
• 化学式: C₁₀H₁₀Se
• 分子量: 209.149
• InChiKey: HNQLFSSNCGDWCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  11
• 可旋转键数：
  2
• 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 p-tolyl selenide 在 水 、 碘 作用下， 以 乙腈 为溶剂， 反应 20.5h， 以72%的产率得到(Z)-2-iodo-3-(p-tolylseleno)-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：

  prop-2-yn-1-yl(p-tolyl)selane 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.17h， 以59%的产率得到1,2-propadienyl p-tolyl 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

• Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes. an efficient synthesis of N-(3-organoseleno-2-iodo-2(Z)-propenyl) acetamidesElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b3/b300879g/
  作者：Shengming Ma、Xueshi Hao、Xian Huang

  DOI：10.1039/b300879g

  日期：2003.4.16

  Z-Selectivity was observed for iodohydroxylation of Se-substituted allenes with I2 and H2O, which is opposite to that of 1,2-allenyl sulfoxides. With n-hexane as the co-solvent Z-iodoamination leading to N-(3-organoseleno-2-iodo-2(Z)-propenyl)acetamide was observed. A brief rational for the stereoselectivity of this reaction is provided.

  观察到Se取代的丙烯与I2和H2O的碘羟基化反应具有Z选择性，这与1,2-丙烯基亚砜的选择性相反。在n-己烷作为共溶剂的情况下，观察到了Z-碘氨化反应，生成N-(3-有机硒基-2-碘-2(Z)-丙烯基)乙酰胺。针对该反应的立体选择性提供了简要的解释。