5-phenylthiopent-3-yn-2-one | 305805-83-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-phenylthiopent-3-yn-2-one
• 英文别名: 5-Phenylsulfanylpent-3-yn-2-one
• CAS: 305805-83-8
• 化学式: C₁₁H₁₀OS
• 分子量: 190.266
• InChiKey: TZPRSZXCXUSXIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-phenylthiopent-3-yn-2-one 在 sodium tetrahydroborate 、 三甲基氯硅烷 、 水 、 sodium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (4Z)-4-iodo-5-phenylthiopent-4-en-2-ol
  参考文献：
  名称：

  Stereoselective Synthesis of (Z)-a-Phenoxymethylene-g-butyrolactone and Its Sulfur Analogues from 2-Propynyloxy- or 2-Propynylthiobenzene

  摘要：

  The preparations of (Z)-alpha -phenoxymethylene-gamma -butyrolactone, alpha -phenoxymethyl-gamma -butyrolactone, (Z)-alpha -phenylthiomethylene-gamma -butyrolactone, and alpha -phenylthiomethyl-gamma -butyrolactone derivatives from 2-propynyloxy-benzene and 2-propynylthiobenzene were described.

  DOI：

  10.3987/com-00-8964
• 作为产物：
  描述：

  5-phenylthiopent-3-yn-2-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以82%的产率得到5-phenylthiopent-3-yn-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of (Z)-a-Phenoxymethylene-g-butyrolactone and Its Sulfur Analogues from 2-Propynyloxy- or 2-Propynylthiobenzene

  摘要：

  The preparations of (Z)-alpha -phenoxymethylene-gamma -butyrolactone, alpha -phenoxymethyl-gamma -butyrolactone, (Z)-alpha -phenylthiomethylene-gamma -butyrolactone, and alpha -phenylthiomethyl-gamma -butyrolactone derivatives from 2-propynyloxy-benzene and 2-propynylthiobenzene were described.

  DOI：

  10.3987/com-00-8964

文献信息

• A Boron–Oxygen Transborylation Strategy for a Catalytic Midland Reduction
  作者：Kieran Nicholson、Joanne Dunne、Peter DaBell、Alexander Beaton Garcia、Andrew D. Bage、Jamie H. Docherty、Thomas A. Hunt、Thomas Langer、Stephen P. Thomas

  DOI：10.1021/acscatal.0c05168

  日期：2021.2.19

  The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron–oxygen transborylation, has been developed and used to transform the stoichiometric borane reagents of the Midland reduction into catalysts. This turnover strategy

  酮的对映选择性氢硼化是教科书上的反应，需要化学计量的对映体富集的硼烷，Midland还原是一个开创性的例子。在这里，已经开发出了一种用于不对称催化的转换策略，即硼-氧转硼化反应，并将其用于将Midland还原反应的化学计量硼烷试剂转化为催化剂。这种转换策略通过酮的对映选择性还原得到证实，其中包括生物活性分子的衍生物和含有可还原基团的酮。在生成对映体富集的硼烷催化剂在原位从市售的试剂，9-硼杂双环[3.3.1]壬烷（H-乙-9-BBN）和β-pine烯，以及频哪醇硼烷（HBpin）进行的B–O硼氢化反应用于催化转换。机理研究表明，B–O / B–H硼交换通过立体固位，一致的过渡态（类似于σ键复分解）使B–O发生转硼化作用。
• Stereoselective Synthesis of (Z)-a-Phenoxymethylene-g-butyrolactone and Its Sulfur Analogues from 2-Propynyloxy- or 2-Propynylthiobenzene
  作者：Fen-Tair Luo、Sheng-Li Ko、Lijun Liu、Hui Chen

  DOI：10.3987/com-00-8964

  日期：——

  The preparations of (Z)-alpha -phenoxymethylene-gamma -butyrolactone, alpha -phenoxymethyl-gamma -butyrolactone, (Z)-alpha -phenylthiomethylene-gamma -butyrolactone, and alpha -phenylthiomethyl-gamma -butyrolactone derivatives from 2-propynyloxy-benzene and 2-propynylthiobenzene were described.