2-(1-Hydroxy-2-methyl-propyl)-hex-5-enedithioic acid ethyl ester | 132786-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1-Hydroxy-2-methyl-propyl)-hex-5-enedithioic acid ethyl ester
• 英文别名: Ethyl 2-(1-hydroxy-2-methylpropyl)hex-5-enedithioate
• CAS: 132786-02-8
• 化学式: C₁₂H₂₂OS₂
• 分子量: 246.438
• InChiKey: RWMZAVGEZROEAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-Hydroxy-2-methyl-propyl)-hex-5-enedithioic acid ethyl ester 在 正丁基锂 、 camphor-10-sulfonic acid 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (2S,6S)-5-But-3-enyl-2-ethyl-6-isopropyl-6H-[1,3]oxathiine
  参考文献：
  名称：

  Preparation of 4-Alkanesulfinyl-Δ4-1,3-oxathianes and Δ4-1,3-oxathianes. On the resistance of endocyclic ketene dithioacetals to nucleophilic attack

  摘要：

  4-Alkanesulfinyl-DELTA4-1,3-oxathianes are formed by oxidation of 4-alkylthio-DELTA4-1,3-oxathianes using metachloroperoxybenzoic acid. Treatment of 4-Alkanesulfinyl-DELTA4-1,3-oxathianes with butyllithium resulted in desulfinylation to simpler DELTA4-1,3-oxthianes in moderate yields. Both alkylthio- and alkanesulfinyl- substituted oxathianes were found to resist attack by nucleophiles precedented to add to ketene dithioacetals. It is speculated that the fixed geometry of the endocyclic C-S bond of these compounds renders them stereoelectronically resistant to nucleophilic attack.

  DOI：

  10.1016/s0040-4039(00)60430-6

文献信息

• Preparation of 4-alkylthio-δ-1,3-oxathianes, novel endocyclic ketene dithioacetals, via an acetalization of β-hydroxydithioesters
  作者：Robert D. Walkup、P.Douglas Boatman

  DOI：10.1016/s0040-4039(00)97216-2

  日期：1990.1

  The treatment of β-hydroxydithioesters with dimethyl or diethyl acetals in the presence of an acid catalyst resulted in the formation of the six-membered endocyclic ketene dithioacetals, 4-alkylthio-Δ4-1,3-oxathianes, via transacetalization.

  β-hydroxydithioesters用二甲基或在酸催化剂的存在下二乙基缩醛的处理导致六元环内烯酮二硫的形成，4-烷硫基-Δ 4 -1,3- oxathianes，经由transacetalization。
• Preparation of 4-Alkanesulfinyl-Δ4-1,3-oxathianes and Δ4-1,3-oxathianes. On the resistance of endocyclic ketene dithioacetals to nucleophilic attack
  作者：Robert D. Walkup、P.Douglas Boatman

  DOI：10.1016/s0040-4039(00)60430-6

  日期：1993.4

  4-Alkanesulfinyl-DELTA4-1,3-oxathianes are formed by oxidation of 4-alkylthio-DELTA4-1,3-oxathianes using metachloroperoxybenzoic acid. Treatment of 4-Alkanesulfinyl-DELTA4-1,3-oxathianes with butyllithium resulted in desulfinylation to simpler DELTA4-1,3-oxthianes in moderate yields. Both alkylthio- and alkanesulfinyl- substituted oxathianes were found to resist attack by nucleophiles precedented to add to ketene dithioacetals. It is speculated that the fixed geometry of the endocyclic C-S bond of these compounds renders them stereoelectronically resistant to nucleophilic attack.