(Z)-3-iodo-2-methyl-4-(phenylsulfanyl)but-3-en-2-ol | 529474-74-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-3-iodo-2-methyl-4-(phenylsulfanyl)but-3-en-2-ol
• 英文别名: (3Z)-3-Iodo-2-methyl-4-(phenylthio)-3-buten-2-ol；(Z)-3-iodo-2-methyl-4-phenylsulfanylbut-3-en-2-ol
• CAS: 529474-74-6
• 化学式: C₁₁H₁₃IOS
• 分子量: 320.194
• InChiKey: GEEQETLUTBRILH-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-1,2-butadienyl phenyl sulfoxide 在 吡啶 、 tetraphosphorus decasulfide 、 水 、 碘 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 (Z)-3-iodo-2-methyl-4-(phenylsulfanyl)but-3-en-2-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

文献信息

• 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.