1,1-dimethoxy-2-(tert-butylthio)propane | 145866-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dimethoxy-2-(tert-butylthio)propane
• 英文别名: 2-(1,1-Dimethoxypropan-2-ylsulfanyl)-2-methylpropane
• CAS: 145866-40-6
• 化学式: C₉H₂₀O₂S
• 分子量: 192.323
• InChiKey: ZHGZSDFYDNMFBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1-叔丁基乙烯氧基)三甲基硅烷 、 1,1-dimethoxy-2-(tert-butylthio)propane 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到6-(tert-butylthio)-5-methoxy-2,2-dimethyl-3-heptanone
  参考文献：
  名称：

  Anti-selective reaction of .alpha.-sulfenyl acetals with silylated carbon nucleophiles. Scope, limitation, and mechanism

  摘要：

  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.

  DOI：

  10.1021/jo00055a009
• 作为产物：
  描述：

  2-甲基-2-丙硫醇钠盐 、 Methanesulfonic acid 2,2-dimethoxy-1-methyl-ethyl ester 以 乙醇 为溶剂， 反应 10.0h， 以40%的产率得到1,1-dimethoxy-2-(tert-butylthio)propane
  参考文献：
  名称：

  Anti-selective reaction of .alpha.-sulfenyl acetals with silylated carbon nucleophiles. Scope, limitation, and mechanism

  摘要：

  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.

  DOI：

  10.1021/jo00055a009

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.