2-ethoxy-[1,3]dithiolane | 65225-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-ethoxy-[1,3]dithiolane
• 英文别名: 2-Ethoxy-1,3-dithiolane
• CAS: 65225-59-4
• 化学式: C₅H₁₀OS₂
• 分子量: 150.266
• InChiKey: HSBIVNAAMSNAGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxy-[1,3]dithiolane 生成 乙醛
  参考文献：
  名称：

  KASATKINA A. A.; BATYRBAEV N. A., HOB. REAKTIVY HA OSNOVE ATSETALEJ, ORTOEHFIROV, IX ANALOGOV I PROIZVODNYX+

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-乙二硫醇 、 原甲酸三乙酯 生成 2-ethoxy-[1,3]dithiolane
  参考文献：
  名称：

  Batyrbaev, N. A.; Zorin, V. V.; Zlotskii, S. S., Journal of Organic Chemistry USSR (English Translation), 1981, p. 1369 - 1371

  摘要：

  DOI：

文献信息

• The Pormylation of an Aromatic Nucleus by the Use of 2-Ethoxy-1,3-dithiolane
  作者：Shigeo Jo、Shigeo Tanimoto、Toyonari Sugimoto、Masaya Okano

  DOI：10.1246/bcsj.54.2120

  日期：1981.7

  The reaction of various phenols with 2-ethoxy-1,3-dithiolane proceeded smoothly in the presence of BF3·Et2O to afford 1,3-dithiolan-2-ylated phenols, which were readily hydrolyzed to the corresponding aldehydes. This process was also extended to N,N-dimethylaniline and indole.

  各种苯酚与2-乙氧基-1,3-二硫杂环戊烷在BF3·Et2O的存在下顺利反应，生成1,3-二硫杂环戊烷-2-基化的苯酚，这些产物易于水解为相应的醛。这一过程也扩展到了N,N-二甲基苯胺和吲哚。
• Lewis Acid Mediated Reaction of Trimethylstyrylsilanes with Thioacetal Derivatives
  作者：Toshikazu Hirao、Shuichiro Kohno、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1246/bcsj.56.1569

  日期：1983.5

  Treatment of trimethylstyrylsilanes with 1-ethoxy-1-(phenylthio)ethane or 2-ethoxy-1,3-dithiolane in the presence of Lewis acid gives the corresponding (E)-allyl sulfide or (E)-2-styryl-1,3-dithiolane, respectively. In both cases, a carbon-oxygen bond of thioacetal derivatives is cleaved selectively.

  在路易斯酸的存在下，将三甲基苯乙烯基硅烷与1-乙氧基-1-苯硫基乙烷或2-乙氧基-1,3-二硫杂环戊烷反应，分别得到相应的(E)-烯丙基硫醚或(E)-2-苯乙烯基-1,3-二硫杂环戊烷。这两种情况下，硫缩醛衍生物中的碳氧键被选择性地断裂。
• The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl₂or HgCl₂
  作者：Shigeo Tanimoto、Shigeo Jo、Toyonari Sugimoto、Masaya Okano

  DOI：10.1246/bcsj.54.3237

  日期：1981.10

  In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C–O or C–S bond) occurs, while the breaking of the exocyclic C–O bond to give the 1,3-oxathiolan-2-ium ion is unfavorable. This behavior is different from that of 2-ethoxy-1,3-dithiolane, in which the breaking of the endocyclic C–S bond

  在 ZnCl2 或 HgCl2 存在下，2-乙氧基-1,3-氧杂硫杂环戊烷与羰基化合物反应，发现仅发生内环键（C-O 或 C-S 键）断裂，而环外 C-O 键断裂产生 1,3-oxathiolan-2-ium 离子是不利的。这种行为不同于 2-乙氧基-1,3-二硫戊环，其中环内 C-S 键通过 HgCl2 和外环 C-O 键发生断裂，通过 ZnCl2。
• The Reaction of 2-Ethoxy-1,3-dithiolane with Carbonyl Compounds
  作者：Shigeo Jo、Shigeo Tanimoto、Tatsuo Oida、Masaya Okano

  DOI：10.1246/bcsj.54.1434

  日期：1981.5

  The reaction of 2-ethoxy-1,3-dithiolane with carbonyl compounds such as aldehydes and ketones was investigated. The reaction proceeded smoothly in the presence of the HgCl2-catalyst to afford 2-substituted and 2,2-disubstituted 1,3-dithiolanes. The reaction also offers an interesting alternative to the previously reported methods of synthesizing 1,3-dithiolanes which involve the acid-catalyzed reaction of carbonyl compounds with 1,2-ethanedithiol.

  研究了2-乙氧基-1,3-二硫烷与醛和酮等羰基化合物的反应。在HgCl2催化剂的存在下，反应顺利进行，得到2-取代和2,2-双取代的1,3-二硫烷。该反应还为合成1,3-二硫烷提供了一种有趣的替代方案，与先前报道的羰基化合物与1,2-乙二硫醇的酸催化反应方法相比。
• Synthesis and Lithiation of 2-Alkylthio- and 2-Arylthio-1,3-dithiolanes
  作者：Shigeo Tanimoto、Tatsuo Oida、Hideyuki Ikehira、Masaya Okano

  DOI：10.1246/bcsj.55.1977

  日期：1982.6

  Several 2-alkylthio- and 2-arylthio-1,3-dithiolanes were synthesized by the reaction of 2-ethoxy-1,3-dithiolane with aliphatic and aromatic thiols in the presence of ZnCl2. The lithiation of 2-alkylthio-1,3-dithiolanes with butyllithium in tetrahydrofuran followed by the addition of alkyl halides gave unsymmetrical dialkyl trithiocarbonates in moderately good yields.

  在 ZnCl2 存在下，通过 2-乙氧基-1,3-dithiolane 与脂肪族和芳香族硫醇的反应合成了几种 2-烷硫基-和 2-芳硫基-1,3-dithiolanes。在四氢呋喃中用丁基锂将 2-烷硫基-1,3-二硫戊烷锂化，然后加入卤代烷，得到不对称的三硫代碳酸二烷基酯，产率适中。