3-methylpenta-1,2-dienyl phenyl sulfide | 77084-85-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methylpenta-1,2-dienyl phenyl sulfide
• 英文别名: Benzene, [(3-methyl-1,2-pentadienyl)thio]-
• CAS: 77084-85-6
• 化学式: C₁₂H₁₄S
• 分子量: 190.309
• InChiKey: TYYNDYRETAWGAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  288.1±13.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3-methylpenta-1,2-dienyl phenyl sulfide 在 水 、 溴 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以86%的产率得到(Z)-2-bromo-3-methyl-1-(phenylsulfanyl)pent-1-en-3-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：

  1-苯基亚磺酰基-3-甲基-1,2-戊二烯 在 吡啶 、 tetraphosphorus decasulfide 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到3-methylpenta-1,2-dienyl 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：——
• Reversed Stereoselectivity in Iodohydroxylation of Allenyl Sulfides. An Efficient Synthesis of (<i>Z</i>)-3-Organosulfur-2-iodo-2-propenols
  作者：Shengming Ma、Xueshi Hao、Xian Huang

  DOI：10.1021/ol034109y

  日期：2003.4.1

  It is observed that the iodohydroxylation of 1,2-allenyl sulfides with 12 and water in aqueous acetone showed Z-selectivity, which is opposite to that of the iodohydroxylation of 1,2-allenyl sulfoxides.
• 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.