(E)-3'-thioxospiro(cyclohexane-1,2'-chroman)-4'-one S-(1-adamantylimide) | 228420-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3'-thioxospiro(cyclohexane-1,2'-chroman)-4'-one S-(1-adamantylimide)
• 英文别名: 3-thioxospiro[chroman-2,1'-cyclohexane]-4-one S-(1-adamantylimide)；3-(1-Adamantylimino-lambda4-sulfanylidene)spiro[chromene-2,1'-cyclohexane]-4-one；3-(1-adamantylimino-λ4-sulfanylidene)spiro[chromene-2,1'-cyclohexane]-4-one
• CAS: 228420-12-0
• 化学式: C₂₄H₂₉NO₂S
• 分子量: 395.566
• InChiKey: KOZRFEDBMDGFDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  39.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3'-thioxospiro(cyclohexane-1,2'-chroman)-4'-one S-(1-adamantylimide) 以 氯苯 为溶剂， 反应 3.0h， 以20%的产率得到trans-tetraspirotrithiolate-5'',3'''-chroman-2''',1''''-cyclohexane>-4',4'''-dione
  参考文献：
  名称：

  New Reactions of Thione S-(tert-Alkylimides).

  摘要：

  Two new alpha-chloro sulfenyl chlorides 1, four new 2-thioxo-1-tetralone S-imides 2 (X = CH2), and one new 3-thioxochroman-4-one S-imide 2 (X = O) have been prepared and characterized by comprehensive spectroscopy and, in one case, an X-ray crystal structure determination. Pyrolysis of 2 leads to the corresponding 1,2,4-trithiolanes 3 after extensive sulfur scrambling. Addition of arenethiols to 2 (R-5 = t-Bu), but not 2 (R-5 = 1-adamantyl), leads to the corresponding adducts 13 with an unusual dithioacetal structure. Ozonolysis of 2 gives the corresponding alpha-diketones such as 16.

  DOI：

  10.3891/acta.chem.scand.53-0284
• 作为产物：
  描述：

  金刚烷胺 、 3-chloro-3-chlorosulfenylspiro-4-one 以 氯仿 为溶剂， 反应 0.25h， 以17.5%的产率得到(E)-3'-thioxospiro(cyclohexane-1,2'-chroman)-4'-one S-(1-adamantylimide)
  参考文献：
  名称：

  New Reactions of Thione S-(tert-Alkylimides).

  摘要：

  Two new alpha-chloro sulfenyl chlorides 1, four new 2-thioxo-1-tetralone S-imides 2 (X = CH2), and one new 3-thioxochroman-4-one S-imide 2 (X = O) have been prepared and characterized by comprehensive spectroscopy and, in one case, an X-ray crystal structure determination. Pyrolysis of 2 leads to the corresponding 1,2,4-trithiolanes 3 after extensive sulfur scrambling. Addition of arenethiols to 2 (R-5 = t-Bu), but not 2 (R-5 = 1-adamantyl), leads to the corresponding adducts 13 with an unusual dithioacetal structure. Ozonolysis of 2 gives the corresponding alpha-diketones such as 16.

  DOI：

  10.3891/acta.chem.scand.53-0284

文献信息

• Reactions of 2,2-Dialkyl-3-thioxochroman-4-one S-(1-Adamantylimides) with Some Nitrilimines
  作者：Mohamed I. Hegab、Mohamed F. El Shehry

  DOI：10.5560/znb.2014-3276

  日期：2014.4.1

  (E)-3-Thioxospiro[chroman-2,1ʹ-cyclohexane]-4-one S-(1-adamantylimide) (1) reacted with numerous nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides - i) in refluxing dry toluene to afford 3ʺ,5ʺ-disubstituted-300H,4ʹHdispiro[ cyclohexane-1,2ʹ-chromene-3ʹ,2ʺ-[1,3,4]thiadiazole]-4ʹ-ones 3a - i. Similarly, reaction of 2,2-dimethyl-3-thioxochroman-4-one S-(1-adamantylimide) (4) with nitrilimines in refluxing dry toluene afforded the corresponding 3ʹ,5ʹ-disubstituted-3,3-dimethyl-3ʹH,4H-spiro[chromene-3,2ʹ- [1,3,4]thiadiazole]-ones 5a - i.

  2a (E)-3-硫氧螺[色满-2,1ʹ-环己烷]-4-酮 S-(1-金刚烷酰亚胺)(1)在回流干燥甲苯中与大量的硝基亚胺（通过三乙胺脱氢卤化相应的肼酰氯-i原位生成）反应，得到 3ʺ、5ʺ-二取代-300H,4ʹH-二螺[环己烷-1,2ʹ-铬-3ʹ,2ʺ-[1,3,4]噻二唑]-4ʹ-酮 3a -i。同样，2,2-二甲基-3-硫酮-4-苯并二氢吡喃酮 S-(1-金刚烷酰亚胺)(4)在回流干燥甲苯中与二rilimines 反应，得到相应的 3ʹ，5ʹ-二取代-3,3-二甲基-3ʹH,4H-螺[色烯-3,2ʹ-[1,3,4]噻二唑]-酮 5a - i。