1-(3,4,4a,5,6,7-Hexahydro-4a-methyl-2-naphthalenyl)ethanone | 139687-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4,4a,5,6,7-Hexahydro-4a-methyl-2-naphthalenyl)ethanone
• 英文别名: 2-acetyl-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene
• CAS: 139687-10-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: FZOXTZZLGAOZSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(3,4,4a,5,6,7-Hexahydro-4a-methyl-2-naphthalenyl)ethanone 在 硫酸 、 双氧水 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 504004.5h， 生成 (2SR,4aRS,8RS)-3,4,4a,5,6,7-hexahydro-4a-methyl-8H,8-(1'',1'',3'',3''-tetramethylisoindolin-2''-yloxyl)-spiro-(naphthalen-2',2'-dimethyl-2,2'-oxirane)
  参考文献：
  名称：

  Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model:  Trapping of Radical Intermediates

  摘要：

  To better understand the skin sensitization mechanism of 15-hydroperoxyabietic acid-like compounds, 2-(1'-hydroperoxy-1'-methylethyl)-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene 7 was synthesized. The allergenic activity of this compound was tested on mice using the local lymph node assay, and further evaluated on guinea pigs using the Freund's complete adjuvant test. Using these methods, hydroperoxide 7 was found to be a strong sensitizer. Radical-trapping experiments were carried out on this compound in the presence of the spin-trapping agent, 1,1,3,3-tetramethylisoindolin-2-yloxyl 17, using light to induce radicals. The formation of carbon-centered radicals derived from compound 7 by intramolecular cyclization of an oxygen-centered radical was observed. The reaction of these intermediates with 17 gave various adducts in a very low yield, but a 1/1 mixture of diastereomers 18a and 18b (0.1% yield) was isolated and characterized, together with compound 19 (0.03% yield). The results suggest that carbon-centered reactive radicals are formed from allylic hydroperoxides and that this could be the possible mechanism involved in allergic contact dermatitis to abietic acid.

  DOI：

  10.1021/tx9901433
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 吡啶 、 盐酸 、 zinc(II) iodide 、 三氯氧磷 作用下， 反应 30.67h， 生成 1-(3,4,4a,5,6,7-Hexahydro-4a-methyl-2-naphthalenyl)ethanone
  参考文献：
  名称：

  （1 R）-和（1 S）-5-demethyl-8,16-methanobacteriorhodopsin及其性质。光学活性和同位素形式的5-demethyl-8,16-methanoretinal的合成和光谱

  摘要：

  （ALL- ë）-5-去甲基-8,16-二methanoretinal在两个旋光对映体（1制备- [R 1个小号），以及在它们的9- Ž和13-Z形式。1 R和1 S形式与细菌视紫红质的相互作用表明，在细菌视紫红质类似物的形成上有明确的手性识别，反映在结合速率和ϵ max值上。具有光学活性发色团的两种细菌视紫红质具有相同的λmax值并显示出与光子驱动质子泵相同的效率。5-甲基的不存在导致质子泵效率比天然系统低50％。另外，对于外消旋的5-去甲基-8,16-二methanoretinal，5- 2 H，7- 2 H，5,7- 2 ħ 2和5,7,16a，16A- 2 ħ 4个同位素中的各种异构形式清一色E，9-Z和13- ż还制备。

  DOI：

  10.1002/recl.19921110104