6-phenoxy-3-thiahexan-1,5-diol | 39093-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-phenoxy-3-thiahexan-1,5-diol
• 英文别名: 2-Propanol, 1-[(2-hydroxyethyl)thio]-3-phenoxy-；1-(2-hydroxyethylsulfanyl)-3-phenoxypropan-2-ol
• CAS: 39093-59-9
• 化学式: C₁₁H₁₆O₃S
• 分子量: 228.312
• InChiKey: VNIURBTZKZGYGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基缩水甘油醚 、 2-巯基乙醇 在 magnesium oxide 、 铜 作用下， 反应 0.33h， 以82%的产率得到6-phenoxy-3-thiahexan-1,5-diol
  参考文献：
  名称：

  无溶剂条件下Cu/MgO催化高效合成β-羟基硫化物和β-羟基亚砜

  摘要：

  使用 Cu/MgO 作为多相催化剂，环氧化物与硫醇的区域选择性、立体选择性和化学选择性开环已被有效地进行，以在室温和无溶剂条件下以优异的产率生产相应的 β-羟基硫化物。在室温下，在相同催化剂的存在下，用硫醇和 50% 的 H2O2 水溶液处理环氧化物以极好的收率提供了 β-羟基亚砜。

  DOI：

  10.1080/00397910903219500

文献信息

• Stereo‐ and Regioselective Thiolysis of 1,2‐Epoxides in Water
  作者：Barahman Movassagh、Mohammad Soleiman‐Beigi

  DOI：10.1080/00397910701548100

  日期：2007.9.1
• Bock; Haberkorn; Herlinger, Arzneimittel-Forschung/Drug Research, 1972, vol. 22, # 9, p. 1564 - 1569
  作者：Bock、Haberkorn、Herlinger、Mayer、Petersen

  DOI：——

  日期：——
• Efficient synthesis of β, β’-dihydroxy sulfides by ring opening of epoxides with mercaptoethanol catalyzed under solvent-free conditions
  作者：Moufida Romdhani-Younes、Mohamed Moncef Chaabouni

  DOI：10.1080/17415993.2012.662685

  日期：2012.4.1

  A simple and highly efficient synthesis of beta, beta'-dihydroxy sulfides has been achieved by ring opening of epoxides with mercaptoethanol using catalytic amount of benzyltrimethylammonium hydroxide (Triton B) under solvent-free conditions. Excellent regioselectivity was found for aliphatic unsymmetrical epoxides, with nucleophilic attack at the less-hindered carbon atom of the epoxide. However, this regioselectivitywas not observed for styrene oxide and a mixture of two isomers was obtained. This process was also regio- and chemo-selective as illustrated using epichlorohydrin with two epoxide ring positions and mercaptoethanol with two functional groups (SH and OH).[GRAPHICS].1a-e 2ae(1)(alpha) 2e(2)(beta)R = CH3(a) ; C2H3(b) ; CICH2(c) ; PhOCH2(d) ; ph(e).
• Routes for reactions of alkylene oxides with R-β-hydroxyalkyl sulfides: Unusual exchange of functional groups
  作者：A. D. Malievskii

  DOI：10.1134/s0965544112010069

  日期：2012.5

  Possible routes of the previously unknown exchange reaction of alkylene oxides with R-beta-hydroxyalkyl sulfides have been considered. Each route has intermediates and transition states of its own, but all the directions in the final stage lead to the formation of a single intermediate cyclic bipolar ion with intramolecular hydrogen bonding, which determines the common nature and composition of end products for all routes. The features of the reaction have been analyzed. The quantitative description of each route has been given.