1,1-dimethoxy-2-(ethylthio)propane | 129844-38-8

• 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-(ethylthio)propane
• 英文别名: 2-Ethylsulfanyl-1,1-dimethoxypropane
• CAS: 129844-38-8
• 化学式: C₇H₁₆O₂S
• 分子量: 164.269
• InChiKey: PMXVTWURVBVHNL-UHFFFAOYSA-N

物化性质

• 沸点：
  194.8±30.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 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-(ethylthio)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88%的产率得到6-(ethylthio)-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：

  Methanesulfonic acid 2,2-dimethoxy-1-methyl-ethyl ester 、 乙硫醇钠 以 乙醇 为溶剂， 反应 10.0h， 以36%的产率得到1,1-dimethoxy-2-(ethylthio)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

• <i>Anti</i>-Cram Selective Reaction of α-Sulfenyl Acetals with Silylated Carbon Nucleophiles
  作者：Kazuhiko Saigo、Kazuaki Kudo、Yukihiko Hashimoto、Hiroki Kimoto、Masaki Hasegawa

  DOI：10.1246/cl.1990.941

  日期：1990.6

  α-Sulfenyl acetals reacted smoothly with silylated carbon nucleophiles such as silyl enol ether, ketene silyl acetal, and allylsilane in the presence of a catalytic amount of Lewis acid mainly to give anti-Cram adducts with high diastereoselectivity by the asymmetric induction of the α-sulfur atom of the acetals.

  在一定量的路易斯酸催化下，α-亚磺酰基乙缩醛与硅烷化碳亲核物（如硅烷烯醇醚、酮烯硅烷缩醛和烯丙基硅烷）顺利发生反应，通过不对称诱导乙缩醛中的α-硫原子，以高非对映选择性生成反克拉姆加合物。
• SAIGO, KAZUHIKO;KUDO, KAZUAKI;HASHIMOTO, YUKIHIKO;KIMOTO, HIROKI;HASEGAWA+, CHEM. LETT.,(1990) N, C. 941-944
  作者：SAIGO, KAZUHIKO、KUDO, KAZUAKI、HASHIMOTO, YUKIHIKO、KIMOTO, HIROKI、HASEGAWA+

  DOI：——

  日期：——
• 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.