2,2-dibutyl-[1,3]dithiolane | 59729-25-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2,2-dibutyl-[1,3]dithiolane
• 英文别名: 2,2-Dibutyl-1,3-dithiolan；2,2-Dibutyl-1,3-dithiolane
• CAS: 59729-25-8
• 化学式: C₁₁H₂₂S₂
• 分子量: 218.428
• InChiKey: OVCKIQROGZGICM-UHFFFAOYSA-N

物化性质

• 沸点：
  292.8±15.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dibutyl-[1,3]dithiolane 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以3.20 g的产率得到5-nonanethiol
  参考文献：
  名称：

  Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility

  摘要：

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.

  DOI：

  10.1021/ja067670a
• 作为产物：
  描述：

  5-壬酮 、 1,2-乙二硫醇 在 α-Zr(O3PCH3)1.2(O3PC6H4SO3H)0.8 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2,2-dibutyl-[1,3]dithiolane
  参考文献：
  名称：

  一种由磺苯基膦酸锆催化制备环状缩酮和硫缩酮的有效方法

  摘要：

  描述了一种使用磺基酚磷酸锆作为催化剂制备环酮和硫酮的便利方法。

  DOI：

  10.1055/s-2001-15155

文献信息

• An Efficient Procedure for the Preparation of Cyclic Ketals and Thioketals Catalyzed by Zirconium Sulfophenyl Phosphonate
  作者：Massimo Curini、Francesco Epifano、Maria Carla Marcotullio、Ornelio Rosati

  DOI：10.1055/s-2001-15155

  日期：——

  A convenient method for the preparation of cyclic ketals and thioketals using zirconium sulfophenyl phosphonate as catalyst is described.

  描述了一种使用磺基酚磷酸锆作为催化剂制备环酮和硫酮的便利方法。
• Reactivity of Ethanediyl<i>S,S</i>-Acetals; 2. Synthesis of 2,3-Dihydro-1,4-dithiins
  作者：Romualdo Caputo、Carla Ferreri、Giovanni Palumbo

  DOI：10.1055/s-1991-26427

  日期：——

  A new, reliable one-step synthesis of 2,3-dihydro-1,4-dithiins from ethanediyl S,S-acetal derivatives of carbonyl compounds is reported.

  报道了一种新颖、可靠的一步合成方法，可以从醛酮化合物的乙烯二基S,S-缩醛衍生物合成2,3-二氢-1,4-二硫烯。
• SATOH, TSUYOSHI;UWAYA, SATORU;YAMAKAWA, KOJI, CHEM. LETT., 1983, N 5, 667-670
  作者：SATOH, TSUYOSHI、UWAYA, SATORU、YAMAKAWA, KOJI

  DOI：——

  日期：——
• Foldamers as Reactive Sieves:  Reactivity as a Probe of Conformational Flexibility
  作者：Ronald A. Smaldone、Jeffrey S. Moore

  DOI：10.1021/ja067670a

  日期：2007.5.1

  A series of m-phenyleneethynylene (mPE) oligomers modified with a dimethylaminopyridine (DMAP) unit were treated with methyl sulfonates of varying sizes and shapes, and the relative reactivities were measured by UV spectrophotometry. Using a small-molecule DMAP analogue as a reference, each of the methyl sulfonates was shown to react at nearly identical rate. In great contrast, oligomers that are long enough to fold, and hence capable of binding the methyl sulfonate, experience rate enhancements of 18-1600-fold relative to that of the small-molecule analogue, depending on the type of alkyl chain attached to the guest. Three different oligomer lengths were studied, with the longest oligomers exhibiting the fastest rate and greatest substrate specificity. Even large, bulky guests show slightly enhanced methylation rates compared to that with the reference DMAP, which suggests a dynamic nature to the oligomer's binding cavity. Several mechanistic models to describe this behavior are discussed.