1-(3-Methyl-but-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol | 64547-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-Methyl-but-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol
• 英文别名: 2,2,6-Trimethyl-1-(3-methyl-3-buten-1-inyl)-cyclohexenol；2,2,6-Trimethyl-1-(3-methylbut-3-en-1-ynyl)cyclohexan-1-ol
• CAS: 64547-54-2
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: GDVNDHNFMFZVOV-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 0.15 Torr)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-Methyl-but-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol 在 氢氧化钾 、 甲酸 作用下， 反应 2.0h， 生成 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-1,4,6-nonatrien-8-in-3-ol
  参考文献：
  名称：

  Baumann,M. et al., Liebigs Annalen der Chemie, 1979, p. 1945 - 1951

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,6-三甲基环己酮 、 2-甲基-1-丁烯-3-炔 生成 1-(3-Methyl-but-3-en-1-ynyl)-2,2,6-trimethyl-cyclohexanol
  参考文献：
  名称：

  由2,2,6-三甲基-环己酮立体定向合成维生素A。

  摘要：

  AbstractAn efficient synthesis of all‐(E) vitamin A acetate from 2,2,6‐trimethyl‐cyclohexanone has been achieved via the intermediacy of 1‐(9‐acetoxy‐3, 7‐dimethyl‐nona‐3,5,7‐trien‐1‐ynyl)‐2,2,6‐trimethyl‐cyclohexanol (25), readily prepared in high yield by allylic rearrangement of tertiary propenols with glacial acetic acid. The key step in the synthesis is the transformation of 25 to the unsaturated ketone 27 (9‐acetoxy‐3,7‐dimethyl‐1‐(2,6,6‐trimethyl‐cyclohex‐1‐enyl)‐nona‐3,5,7‐trien‐ 2‐one) using a novel vanadium(V)‐catalysed rearrangement reaction. The carbonyl in 27 affords the means for the essential isomerization of the adjacent double bond to the (E) isomer and the product is readily transformed into the polyene by reduction and elimination. An overall yield of 18–31% of vitamin A acetate from 2,2,6‐trimethyl‐cyclohexanone has been realized.

  DOI：

  10.1002/hlca.19760590222

文献信息

• A Stereospecific Synthesis of Vitamin A from 2,2,6-Trimethyl-cyclohexanone
  作者：Gary L. Olson、H.-C. Cheung、Keith D. Morgan、Ren� Borer、Gabriel Saucy

  DOI：10.1002/hlca.19760590222

  日期：1976.3.10

  AbstractAn efficient synthesis of all‐(E) vitamin A acetate from 2,2,6‐trimethyl‐cyclohexanone has been achieved via the intermediacy of 1‐(9‐acetoxy‐3, 7‐dimethyl‐nona‐3,5,7‐trien‐1‐ynyl)‐2,2,6‐trimethyl‐cyclohexanol (25), readily prepared in high yield by allylic rearrangement of tertiary propenols with glacial acetic acid. The key step in the synthesis is the transformation of 25 to the unsaturated ketone 27 (9‐acetoxy‐3,7‐dimethyl‐1‐(2,6,6‐trimethyl‐cyclohex‐1‐enyl)‐nona‐3,5,7‐trien‐ 2‐one) using a novel vanadium(V)‐catalysed rearrangement reaction. The carbonyl in 27 affords the means for the essential isomerization of the adjacent double bond to the (E) isomer and the product is readily transformed into the polyene by reduction and elimination. An overall yield of 18–31% of vitamin A acetate from 2,2,6‐trimethyl‐cyclohexanone has been realized.
• BAUMANN M.; HOFFMANN W.; NUERRENBACH A., LIEBIGS ANN. CHEM., 1979, NO 12, 1945-1951
  作者：BAUMANN M.、 HOFFMANN W.、 NUERRENBACH A.

  DOI：——

  日期：——
• US4088681A
  申请人：——

  公开号：US4088681A

  公开（公告）日：1978-05-09
• Baumann,M. et al., Liebigs Annalen der Chemie, 1979, p. 1945 - 1951
  作者：Baumann,M. et al.

  DOI：——

  日期：——