2-n-butyl-1,3-dithiane | 21792-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: 2-n-butyl-1,3-dithiane
• 英文别名: 2-butyl-<1,3>-dithiane；2-(n-Butyl)-1,3-dithiane；2-butyl-1,3-dithiane；2-butyl-1,3-dithian；2-butyldithiane；2-butyl-[1,3]dithiane
• CAS: 21792-53-0
• 化学式: C₈H₁₆S₂
• 分子量: 176.347
• InChiKey: SNFKIFRRRLEODN-UHFFFAOYSA-N

物化性质

• 沸点：
  51 °C(Press: 0.5 Torr)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  10
• 可旋转键数：
  3
• 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-n-butyl-1,3-dithiane 在 六甲基磷酰三胺 、 正丁基锂 、 硼酸三甲酯 、 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 以58%的产率得到potassium (2-n-butyl-1,3-dithian-2-yl)trifluoroborate
  参考文献：
  名称：

  Synthesis of potassium and tetra n-butylammonium 2-substituted-1,3-dithianotrifluoroborate salts and addition to chiral cyclic N-acyliminium ions

  摘要：

  The synthesis of potassium 2-substituted-1,3-dithianotrifluoroborate salts and tetra-n-butyl ammonium derivatives is described. The reaction proceeds under mild reaction conditions and the corresponding products were obtained in moderate to good yields. The reactivity of these compounds in rections with chiral cyclic N-acyliminium ions was evaluated.

  DOI：

  10.1016/j.tet.2008.05.085
• 作为产物：
  描述：

  2-Butyl-1,3-dithian-2-ylium-tetrafluoroborat 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.03h， 以82%的产率得到2-n-butyl-1,3-dithiane
  参考文献：
  名称：

  Klaveness, Jo; Undheim, Kjell, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 8, p. 687 - 692

  摘要：

  DOI：

文献信息

• Activation and synthetic applications of thiostannanes. Conversion of aldehydes and acetals into 1,3-dithianes with high chemodifferentiation
  作者：Tsuneo Sato、Enji Yoshida、Takamichi Kobayashi、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/s0040-4039(00)80396-2

  日期：1988.1

  Novel method for transforming aldehydes and acetals into 1,3-dithianes has been achieved with the aid of organotin thioalkoxides and organotin triflates. Under these reaction conditions, various acid-sensitive groups are tolerated. Differentiation between aromatic or aliphatic aldehydes and acetals has been realized.

  借助于有机锡硫代醇盐和有机锡三氟甲磺酸酯，已经实现了将醛和乙缩醛转化为1，3-二硫杂环己烷的新方法。在这些反应条件下，可以耐受各种酸敏感性基团。已经实现了芳族或脂族醛与缩醛之间的区分。
• SBA-15 functionalized sulfonic acid containing a confined hydrophobic and acidic ionic liquid: a highly efficient catalyst for solvent-free thioacetalization of carbonyl compounds at room temperature
  作者：Babak Karimi、Majid Vafaeezadeh

  DOI：10.1039/c3ra42286k

  日期：——

  SBA-15 functionalized sulfonic acid containing a confined ionic liquid has been introduced to convert various carbonyl compounds to their corresponding dithioacetals and dithioketals at room temperature and under solvent-free conditions. It was found that coating SBA-15-Pr-SO3H with the hydrophobic and acidic ionic liquid [OMIm]HSO4 at a loading of 0.8 mL g−1 of silica, afforded paths for faster mass transfer

  引入了一种含有受限离子液体的SBA-15官能化磺酸的新应用，可在室温和无溶剂条件下将各种羰基化合物转化为其相应的二硫缩醛和二硫缩酮。发现以0.8 mL g -1的二氧化硅负载疏水性和酸性离子液体[OMIm] HSO 4涂覆SBA-15-Pr-SO 3 H ，提供了将原料更快地质量转移到SBA-15-Pr-SO 3 H中的途径。活动站点。同时，由于酸性位点的协同作用机理，它也可能增加布朗斯台德酸的强度。催化剂可以很容易地回收和再利用至少八个反应循环，而其催化活性只有轻微的损失。
• Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals
  作者：Majid Ghashang

  DOI：10.1007/s11164-012-0802-8

  日期：2013.7

  Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in acetonitrile as solvent.

  硫酸氢铝作为一种非均相固体酸催化剂，已被用于在环境条件下使用1,2-和1,3-二硫醇将羰基化合物温和地转化为其硫缩醛，反应时间短，在乙腈中的转化率高至优异。溶剂。
• Synthesis of Fully Substituted Polyhydroxylated Pyrrolizidines via Cope–House Cyclization
  作者：Wei Zhang、Kasumi Sato、Atsushi Kato、Yue-Mei Jia、Xiang-Guo Hu、Francis X. Wilson、Renate van Well、Graeme Horne、George W. J. Fleet、Robert J. Nash、Chu-Yi Yu

  DOI：10.1021/ol201749c

  日期：2011.8.19

  Total synthesis of the proposed structure of (−)-hyacinthacine C5 and its epimers at C6 and C7 is described. A key step of the synthesis was the construction of the bicyclic pyrrolizidine system by means of a nucleophilic addition of a dithiane to a cyclic nitrone followed by a Cope–House cyclization.

  描述了拟合成的（-）-扁豆氨酸C 5结构及其在C6和C7的差向异构体的全合成。合成的关键步骤是通过将二噻吩亲核加成到环状硝酮中，然后进行Cope-House环化反应，来构建双环吡咯烷烷体系。
• Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent
  作者：Haifeng Yu、Dewen Dong、Yan Ouyang、Qun Liu

  DOI：10.1139/v05-184

  日期：2005.10.1

  Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.

  无味的2-(1,3-二硫杂环戊烷-2-亚基)-3-氧代丁酸(1c)被制备并研究其在羰基化合物的硫缩醛化反应中作为1,3-丙二硫醇当量的应用。结果显示，在室温或回流温度下，存在乙酰氯的情况下，各种羰基化合物2与1c的硫缩醛化反应进行得很顺利，并以高收率(高达99%)得到了相应的二硫代缩醛3。此外，硫缩醛化在醛和酮之间表现出高化学选择性。关键词：化学选择性，2-(1,3-二硫杂环戊烷-2-亚基)-3-氧代丁酸，α-氧代酮烯二硫代缩醛，1,3-丙二硫醇当量，硫缩醛化。

表征谱图