2-(cyclopentylidenyl)ethenyl phenyl sulfide | 77084-80-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(cyclopentylidenyl)ethenyl phenyl sulfide
• 英文别名: [(2-Cyclopentylidenevinyl)sulfanyl]benzene
• CAS: 77084-80-1
• 化学式: C₁₃H₁₄S
• 分子量: 202.32
• InChiKey: FRFQVJZQWSMXKX-UHFFFAOYSA-N

物化性质

• 沸点：
  327.8±15.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(cyclopentylidenyl)ethenyl phenyl sulfide 在 水 、 碘 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以37%的产率得到(Z)-1-(1'-cyclopentenyl)-1-iodo-2-(phenylsulfanyl)ethene
  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：

  1,1-Tetramethylen-3-phenylsulfinyl-allen 在 吡啶 、 tetraphosphorus decasulfide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2-(cyclopentylidenyl)ethenyl phenyl sulfide
  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

• Phenylthiocopper trimethylphosphite complex. A reagent for the preparation of thioallenes.
  作者：Alexander J. Bridges

  DOI：10.1016/s0040-4039(00)92184-1

  日期：——
• Studies on the Regio- and Stereoselectivity of Halohydroxylation of 1,2-Allenyl Sulfides or Selenides
  作者：Shengming Ma、Xueshi Hao、Xiaofeng Meng、Xian Huang

  DOI：10.1021/jo049593c

  日期：2004.8.1

  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.