dimenthyl sulfite | 26510-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dimenthyl sulfite
• 英文别名: bis[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] sulfite
• CAS: 26510-92-9
• 化学式: C₂₀H₃₈O₃S
• 分子量: 358.586
• InChiKey: WKQYCOIHFDJKQT-XRNRSJMDSA-N

物化性质

• 熔点：
  52 °C
• 沸点：
  210 °C(Press: 9 Torr)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimenthyl sulfite 在 叔丁基锂 、 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以100%的产率得到2-Methyl-propane-2-sulfinic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  A general route to enantiomerically pure sulfoxides from a chiral sulfite

  摘要：

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.

  DOI：

  10.1021/jo00021a008
• 作为产物：
  描述：

  L-薄荷醇 在 T406石油添加剂 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到dimenthyl sulfite
  参考文献：
  名称：

  Thionyl Chloride-Benzotriazole in Methylene Chloride: A Convenient Solution for Conversion of Alcohols and Carboxylic Acids Expeditiously into Alkyl Chlorides and Acid Chlorides by Simple Titration

  摘要：

  在干燥的二氯甲烷中，以1:1等量混合的亚硫酰氯和苯并三唑溶液，在室温下能高效地将醇和羧酸分别转化为相应的烷基氯化物和酰氯，且通过简单的滴定法即可获得极佳的产率。

  DOI：

  10.1055/s-1999-2943

文献信息

• Rearrangement in Stereoretentive Syntheses of Menthyl Chloride from Menthol: Insight into Competing Reaction Pathways through Component Quantification Analysis
  作者：Lukas Hintermann、Kit Ming Wong

  DOI：10.1002/ejoc.201700677

  日期：2017.10.10

  three regioisomeric tertiary chloromenthanes (9, 10, 11), and both a secondary (12) and tertiary chloride (16) derived from ψ-menthane (1-isobutyl-3-methylcyclopentane). A scheme of rearrangement pathways starting from a common menthyl carbenium ion pair is derived. The effect of purification protocols on crude 2 has been studied quantitatively. Either selective solvolysis of tertiary sideproducts (98

  对映纯试剂薄荷基氯 (2) 通常由 (-)-(1R)-薄荷醇 (1) 与 Lucas 试剂（ZnCl2 浓盐酸水溶液）在立体保留反应中制备，该反应似乎没有伴随的重排。最近通过 TiCl4 催化从氯亚硫酸薄荷酯中挤出 SO2 合成 2 也是如此 (3)。现在已经通过定量 1H 和 13C NMR 方法分析了两种合成的产物，并且所有反应组分都已鉴定到≤0.5 mol% 的水平。任一反应都伴随着达到 18-25 mol% 的相当程度的阳离子重排。除了预期的 2、新薄荷酰氯 (4) 和五种重排产物外，还鉴定了三种区域异构叔氯薄荷烷 (9, 10, 11)，以及衍生自ψ-薄荷烷（1-异丁基-3-甲基环戊烷）的仲氯化物（12）和叔氯化物（16）。推导出了从常见的薄荷基碳鎓离子对开始的重排途径方案。已定量研究纯化方案对粗品 2 的影响。三级副产物的选择性溶剂分解（纯度 98 mol%）或低温结晶（纯度≥97
• Foster et al., Journal of the Chemical Society, 1956, p. 2589,2590
  作者：Foster et al.

  DOI：——

  日期：——
• Thionyl Chloride-Benzotriazole in Methylene Chloride: A Convenient Solution for Conversion of Alcohols and Carboxylic Acids Expeditiously into Alkyl Chlorides and Acid Chlorides by Simple Titration
  作者：Sachin S. Chaudhari、Krishnacharya G. Akamanchi

  DOI：10.1055/s-1999-2943

  日期：1999.11

  A solution of 1 : 1 equivalent of thionyl chloride and benzotriazole in dry methylene chloride efficiently transforms alcohols and carboxylic acids into the corresponding alkyl chlorides and acid chlorides respectively at room temperature, with excellent yields by simple titration.

  在干燥的二氯甲烷中，以1:1等量混合的亚硫酰氯和苯并三唑溶液，在室温下能高效地将醇和羧酸分别转化为相应的烷基氯化物和酰氯，且通过简单的滴定法即可获得极佳的产率。
• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.