2-(1,3-dithian-2-yl)-3-hydroxycyclohex-2-enone | 201008-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,3-dithian-2-yl)-3-hydroxycyclohex-2-enone
• 英文别名: 2-(1,3-Dithian-2-yl)cyclohexane-1,3-dione；2-(1,3-dithian-2-yl)cyclohexane-1,3-dione
• CAS: 201008-54-0
• 化学式: C₁₀H₁₄O₂S₂
• 分子量: 230.352
• InChiKey: UNLMUZKGRPNQIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1,3-dithian-2-yl)-3-hydroxycyclohex-2-enone 在 iron(III) chloride 、 Ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到2-(aminomethylene)cyclohexane-1,3-dione
  参考文献：
  名称：

  Iron-Catalyzed Aminolysis of β-Carbonyl 1,3-Dithianes: Synthesis of Stereodefined β-Enaminones and 3,4-Disubstituted Pyrazoles

  摘要：

  A novel iron-catalyzed aminolysis of beta-carbonyl 1,3-dithianes with various amines including ammonia, primary and secondary amines, as well as hydrazine hydrate has been developed, leading to the synthesis of steleodefined beta-enaminones and 3,4-disubstituted pyrazoles in good to high yields.

  DOI：

  10.1021/ol200246x
• 作为产物：
  描述：

  2-(1,3-dithian-2-ylidene)-cyclohexane-1,3-dione 在 锌 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以53%的产率得到2-(1,3-dithian-2-yl)-3-hydroxycyclohex-2-enone
  参考文献：
  名称：

  通过还原烯酮二硫缩醛制备杂环合成的基本方法

  摘要：

  已经开发出两种允许有效还原乙烯酮二硫缩醛得到取代的二噻烷的通用方法。用甲醇中的镁还原不如用乙酸中的锌还原可靠。镁在甲醇中的更大不一致性已经通过底物的循环伏安研究进行了研究。二环乙烷的用途已通过环化成功地说明，以在脱保护后提供各种杂环醛。

  DOI：

  10.1016/s0040-4020(97)10136-3

文献信息

• Copper-Mediated C−N Bond Formation via Direct Aminolysis of Dithioacetals
  作者：Jing Kang、Fushun Liang、Shao-Guang Sun、Qun Liu、Xi-He Bi

  DOI：10.1021/ol060763c

  日期：2006.6.1

  to the C-N bond formation via direct aminolysis of dithioacetals 2 and 5 with ammonia, primary or secondary amines are developed under mild conditions. Enaminones 3 and 6 were thus obtained in high to excellent yields with high chemoselectivity. This type of aminolysis reaction presents a new synthetic application of the dithioacetal functionality. [reaction: see text]

  在温和条件下，乙酸铜介导了一种通过二硫缩醛2和5与氨，伯胺或仲胺直接氨解形成CN键的有效方法。因此以高至优异的产率和高的化学选择性获得了烯胺酮3和6。这种类型的氨解反应代表了二硫缩醛官能团的新合成应用。[反应：看文字]
• Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals
  作者：John M Mellor、Stephen R Schofield、Stewart R Korn

  DOI：10.1016/s0040-4020(97)10136-3

  日期：1997.12

  Two general methods have been developed permitting the effective reduction of ketene dithioacetals to give substituted dithianes. Reduction with magnesium in methanol is less reliable than reduction with zinc in acetic acid. The greater inconsistency of magnesium in methanol has been investigated by a cyclic voltammetric study of the substrates. The utility of the dithianes has been successfully illustrated

  已经开发出两种允许有效还原乙烯酮二硫缩醛得到取代的二噻烷的通用方法。用甲醇中的镁还原不如用乙酸中的锌还原可靠。镁在甲醇中的更大不一致性已经通过底物的循环伏安研究进行了研究。二环乙烷的用途已通过环化成功地说明，以在脱保护后提供各种杂环醛。
• Iron-Catalyzed Aminolysis of β-Carbonyl 1,3-Dithianes: Synthesis of Stereodefined β-Enaminones and 3,4-Disubstituted Pyrazoles
  作者：Yeming Wang、Xihe Bi、Wei-Qi Li、Dehua Li、Qian Zhang、Qun Liu、Brim Stevy Ondon

  DOI：10.1021/ol200246x

  日期：2011.4.1

  A novel iron-catalyzed aminolysis of beta-carbonyl 1,3-dithianes with various amines including ammonia, primary and secondary amines, as well as hydrazine hydrate has been developed, leading to the synthesis of steleodefined beta-enaminones and 3,4-disubstituted pyrazoles in good to high yields.