Cyclohexancarboxaldehyde hemithioethyleneacetal | 86554-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: Cyclohexancarboxaldehyde hemithioethyleneacetal
• 英文别名: 2-(cyclohexyl)-1,3-oxathiolane；2-Cyclohexyl-1,3-oxathiolane
• CAS: 86554-09-8
• 化学式: C₉H₁₆OS
• 分子量: 172.291
• InChiKey: QAFNGXSQSVTBCV-UHFFFAOYSA-N

物化性质

• 沸点：
  268.2±33.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己酮 在 四甲基乙二胺 、 仲丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 Cyclohexancarboxaldehyde hemithioethyleneacetal
  参考文献：
  名称：

  合成中的硅17：氯甲基（三甲基硅烷基）锂，用于将醛和酮直接转化为⇌，β，-环氧三甲基硅烷的新型试剂

  摘要：

  chloromethyltrimethylsilane的治疗1用仲丁基锂在THF中在-78℃氯甲基产生（三-甲基甲硅烷基）锂4。的治疗4与各种醛和酮给出⇌，β-epoxytrimethylsilanes 5-28，它在酸性水解给予同系化的醛。

  DOI：

  10.1016/s0040-4020(01)88585-9

文献信息

• LiBF₄ Catalyzed Chemoselective Conversion of Aldehydes to 1,3-Oxathiolanes and 1,3-Dithianes
  作者：J. S. Yadav、B. V. S. Reddy、Sushil Kumar Pandey

  DOI：10.1055/s-2001-10780

  日期：——

  Lithium tetrafluoroborate is found to be an efficient catalyst for the chemoselective protection of both aromatic and aliphatic aldehydes as 1,3-oxathiolanes and 1,3-dithianes under mild reaction conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.

  四氟硼酸锂被发现是一种高效的催化剂，可以在温和的反应条件下对芳香醛和脂肪醛进行化学选择性保护，生成1,3-氧硫环烷和1,3-二硫烷。由于反应条件中性，这种方法与酸敏感底物相容。
• Amberlyst® 15 as a Mild, Chemoselective and Reusable Heterogeneous Catalyst for the Conversion of Carbonyl Compounds to 1,3-Oxathiolanes
  作者：Roberto Ballini、Giovanna Bosica、Raimondo Maggi、Alessandro Mazzacani、Paolo Righi、Giovanni Sartori

  DOI：10.1055/s-2001-17532

  日期：——

  Conversion of Carbonyl Compounds to 1,3-Oxathiolanes R berto Ballini,*a Giovanna Bosica,a Raimondo Maggi,*b Alessandro Mazzacani,b Paolo Righi,c Giovanni Sartorib a Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy b Dipartimento di Chimica Organica e Industriale dell'Università, Parco Area delle Scienze 17A, 43100 Parma, Italy c Dipartimento di Chimica

  羰基化合物转化为 1,3-氧硫杂环戊烷 R berto Ballini,*a Giovanna Bosica,a Raimondo Maggi,*b Alessandro Mazzacani,b Paolo Righi,c Giovanni Sartorib a Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy b Dipartimento di Chimica Organica e Industriale dell'Università, Parco Area delle Scienze 17A, 43100 Parma, Italy c Dipartimento di Chimica Organica 'A. Mangini' dell'Università
• Indium Trifluoromethanesulfonate as a Mild and Chemoselective Catalyst for the Conversion of Carbonyl Compounds into 1,3-Oxathiolanes
  作者：Tsuneo Sato、Kiyoshi Kazahaya、Nao Hamada、Shinya Ito

  DOI：10.1055/s-2002-33541

  日期：——

  An efficient method for the preparation of 1,3-oxathiolanes from aldehydes and ketones with 2-mercaptoethanol in the presence of a catalytic amount of indium trifluoromethanesulfonate is reported.

  报道了在催化量的三氟甲磺酸铟存在下，用 2-巯基乙醇从醛和酮制备 1,3-氧杂硫杂环戊烷的有效方法。
• Blue LED-Promoted Oxathiacetalization of Aldehydes and Ketones
  作者：You-Chen Liu、Daggula Mallikarjuna Reddy、Xin-An Chen、Yi-Chen Shieh、Chin-Fa Lee

  DOI：10.1002/ejoc.202000218

  日期：2020.5.10

  A visible‐light‐promoted oxathiacetalization of aldehydes and ketones with 2‐mercaptoethanol and 3‐mercaptopropan‐1‐ol in the presence of eosin Y as catalyst is described leading to the formation of 1,3‐oxathiolanes and 1,3‐oxathianes at ambient temperature and under metal‐free conditions. The solvent is playing vital role in the protection of carbonyl compounds with mercaptoalcohol.

  描述了在曙红Y的催化下，使用2-巯基乙醇和3-巯基丙烷-1-醇在可见光条件下促进醛和酮的乙二醛乙醛缩醛化反应，从而导致1,3-氧杂硫杂环戊烷和1,3-氧杂蒽环的形成环境温度和无金属条件下。溶剂在用巯基醇保护羰基化合物中起着至关重要的作用。
• Silica Gel-Supported Polyphosphoric Acid (PPA/SiO₂) as an Efficient and Reusable Catalyst for Conversion of Carbonyl Compounds into Oxathioacetals and Dithioacetals
  作者：Tadashi Aoyama、Toshio Takido、Mitsuo Kodomari

  DOI：10.1055/s-2004-832812

  日期：——

  A simple and efficient method for the conversion of carbonyl compounds to oxathioacetals and dithioacetals by using polyphosphoric acid supported on silica gel (PPA/SiO2) as an acid catalyst have been developed. PPA/SiO2 is easily recovered from the reaction mixture and reused without a decrease in catalytic ­activity.

  开发了一种简单高效的方法，通过使用负载在硅胶上的多磷酸（PPA/SiO2）作为酸催化剂，将羰基化合物转化为氧硫酯和二硫酯。PPA/SiO2可以轻松从反应混合物中回收，并且在重复使用时没有催化活性下降。