5-methoxy-2,2-dimethyl-6-phenyl-6-(phenylthio)-3-hexanone | 121862-20-2

• 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-methoxy-2,2-dimethyl-6-phenyl-6-(phenylthio)-3-hexanone
• 英文别名: 5-Methoxy-2,2-dimethyl-6-phenyl-6-phenylsulfanylhexan-3-one
• CAS: 121862-20-2
• 化学式: C₂₁H₂₆O₂S
• 分子量: 342.502
• InChiKey: DTSBHWGKYAODQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Methoxy-1-phenyl-2-phenylsulfanylethanol 在 正丁基锂 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 5-methoxy-2,2-dimethyl-6-phenyl-6-(phenylthio)-3-hexanone
  参考文献：
  名称：

  从β-甲氧基-γ-苯硫基酮可通过新颖的苯硫醚迁移反应合成1,3-和1,4-二酮

  摘要：

  1,3-和1,4-二酮均得自常见的前体β-甲氧基-γ-苯硫基酮。这些化合物通过醛加成物与甲氧基（苯硫基）-甲烷接触烯醇甲硅烷基醚后的新型苯硫基迁移反应而衍生。由此获得的化合物被转化为1，3-和1，4-二酮。

  DOI：

  10.1016/s0040-4039(01)80331-2

文献信息

• Anti-selective reaction of .alpha.-sulfenyl acetals with silylated carbon nucleophiles. Scope, limitation, and mechanism
  作者：Kazuaki Kudo、Yukihiko Hashimoto、Makoto Sukegawa、Masaki Hasegawa、Kazuhiko Saigo

  DOI：10.1021/jo00055a009

  日期：1993.1

  In the presence of a Lewis acid, alpha-sulfenyl acetals 1 reacted with various silylated carbon nucleophiles 2 to give anti adducts (anti-3) with high diastereoselectivity. The stereochemistry was only slightly affected by the reaction conditions, such as temperature, solvent, and Lewis acid. However, the structure of substrate 1 and the kind of nucleophile 2 had considerable effect on the stereochemical course of the reaction. Almost exclusive anti selectivity was attained when 1,1-dimethoxy-2-(tert-butylthio)propane (1b) was used as a substrate or when ketene silyl acetal 2c was employed as a nucleophile. The mechanism of this reaction is essentially S(N)2, although the S(N)1 process participates to a various extent, depending on the structure of substrate 1. The usefulness of this anti-selective reaction was exemplified by the easy transformation of anti-3o to synthetically valuable allylic alcohol anti-6 without any loss of stereochemical information. The reaction of alpha-(benzyloxy)acetal 4 with 2 was also investigated. It gave a syn-rich mixture of diastereomers with lower selectivity.
• SATO, TSUNEO;INOUE, MASAMI;KOBARA, SATORU;OTERA, JUNZO;NOZAKI, HITOSI, TETRAHEDRON LETT., 30,(1989) N 1, C. 91-94
  作者：SATO, TSUNEO、INOUE, MASAMI、KOBARA, SATORU、OTERA, JUNZO、NOZAKI, HITOSI

  DOI：——

  日期：——
• Divergent synthesis of 1,3- and 1,4-diketones from β-methoxy-γ-phenylthio ketones accessible through novel phenylthio migration reaction
  作者：Tsuneo Sato、Masami Inoue、Satoru Kobara、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(01)80331-2

  日期：——

  Both 1,3- and 1,4-diketones are obtained from common precursors, β-methoxy-γ-phenylthio ketones. These compounds are derived through the novel phenylthio migration reaction of the aldehyde adducts with methoxy(phenylthio)-methane upon exposure to enol silyl ethers. The compounds thus obtained are converted into 1,3- and 1,4-diketones.

  1,3-和1,4-二酮均得自常见的前体β-甲氧基-γ-苯硫基酮。这些化合物通过醛加成物与甲氧基（苯硫基）-甲烷接触烯醇甲硅烷基醚后的新型苯硫基迁移反应而衍生。由此获得的化合物被转化为1，3-和1，4-二酮。