(1E)-2-(6',6'-dimethylcyclohex-1'-enyl)-N,N-dimethylethen-1-ylamine | 105962-05-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1E)-2-(6',6'-dimethylcyclohex-1'-enyl)-N,N-dimethylethen-1-ylamine
• 英文别名: (E)-2-(6,6-dimethylcyclohexen-1-yl)-N,N-dimethylethenamine
• CAS: 105962-05-8
• 化学式: C₁₂H₂₁N
• 分子量: 179.305
• InChiKey: FRXAUGRZCMNBMA-CSKARUKUSA-N

物化性质

• 沸点：
  50-53 °C(Press: 0.05 Torr)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1E)-2-(6',6'-dimethylcyclohex-1'-enyl)-N,N-dimethylethen-1-ylamine 在 silica gel 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 5,5-Dimethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  二烯胺为Diels-Alder二烯。新的苯并环序列

  摘要：

  （E）-二胺1-7与丙酸甲酯之间的Diels-Alder反应，然后从中间体环加合物III中消除Me 2 NH，可以得到高收率的芳香族甲基酯8-14。

  DOI：

  10.1016/s0040-4039(00)84077-0
• 作为产物：
  描述：

  2,2-二甲基环己酮 在 <(Ph3SiO)2V(O)> 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 21.0h， 生成 (1E)-2-(6',6'-dimethylcyclohex-1'-enyl)-N,N-dimethylethen-1-ylamine
  参考文献：
  名称：

  通过二烯胺[4 + 2]环加成反应的区域选择性环己醛化方法。官能化十氢化萘的合成†

  摘要：

  区域选择性cyclohexannulation过程，其关键的步骤涉及dienamines的[4 + 2]环加成12-24与丙烯酸甲酯，允许环烷酮的转化1-11双环dienoates 25 - 37。简要检查了26的化学性质，并在有关功能化5,5,9-三甲基十氢化萘的感官研究中，描述了37向酮44和46以及向乙酸酯53-56的转化。

  DOI：

  10.1002/hlca.19890720505

文献信息

• Stereoselectivity of Dienamine [4 + 2] Cycloadditions Synthesis of Functionalised Decalins and Drimanes
  作者：Roger L. Snowden、Robert Brauehli、Manfred Wüst

  DOI：10.1002/hlca.19900730313

  日期：1990.5.2

  The [4 + 2] cycloaddition stereoselectivity of dienamines 1–4 with dimethyl fumarate and fumaronitrile has been investigated, and functionalised decalins 21–40 have been prepared by elimination of Me2NH from cycloadducts 7–11 and 15–20; in the context of the synthesis of drimane sesquiterpenes, the reduction of dienediesters 29 and 30 is also described.

  已经研究了二烯胺1–4与富马酸二甲酯和富马腈的[4 + 2]环加成立体选择性，并通过从环加合物7-11和15-20中消除Me 2 NH来制备官能化的十氢化萘21-40。在合成树烯倍半萜的背景下，还描述了二二酯29和30的还原。
• Dienamines as Diels-Alder dienes. An efficient cyclohexannulation sequence
  作者：Roger L. Snowden、Manfred Wüst

  DOI：10.1016/s0040-4039(00)84076-9

  日期：1986.1
• Total Synthesis of Aegyptinones A and B
  作者：Rick L. Danheiser、David S. Casebier、Alexandre H. Huboux

  DOI：10.1021/jo00096a027

  日期：1994.8

  This paper describes the first total syntheses of the diterpene quinones aegyptinones A and B via an extremely direct route which should easily accommodate the production of gram quantities of each compound. The key step in the synthetic strategy involves the application of a recently developed ''second-generation'' photochemical aromatic annulation method for the construction of highly substituted aromatic systems. The synthesis of one of the annulation components, the diazo ketone 5, was achieved using a Diels-Alder-based benzannulation strategy employing cyanoallene and the dienamine 13. Cyanoallene proved to be uniquely effective for this cycloaddition, which either failed or proceeded in poor yield using several substituted acetylenes as dienophiles. The pivotal aromatic annulation reaction was accomplished by irradiating a solution of the diazo ketone 5 and the readily available siloxyalkyne 4 in a Pyrex vessel with a 450-W medium-pressure Hanovia lamp at room temperature for 17-20 h. The desired tricyclic phenol 3 was produced in 58-70% yield and was then converted to aegyptinone B (2) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen. Finally, cyclization to generate aegyptinone A was accomplished in high yield by brief exposure of 2 to an ethanolic solution of concentrated sulfuric acid at room temperature. Overall, this strategy provides efficient routes (six and seven steps, respectively) to aegyptinones A and B which should facilitate the systematic investigation of the pharmacological activity of these novel diterpenes.
• SNOWDEN, ROGER L.;LINDER, SIMON M.;WUST, MANFRED, HELV. CHIM. ACTA., 72,(1989) N, C. 892-905
  作者：SNOWDEN, ROGER L.、LINDER, SIMON M.、WUST, MANFRED

  DOI：——

  日期：——
• SNOWDEN, ROGER L.;BRAUCHLI, ROBERT;WUST, MANFRED, HELV. CHIM. ACTA, 73,(1990) N, C. 640-651
  作者：SNOWDEN, ROGER L.、BRAUCHLI, ROBERT、WUST, MANFRED

  DOI：——

  日期：——