(6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde | 888410-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde
• 英文别名: (1R,9R)-10,10-dimethyl-3-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene-4-carbaldehyde
• CAS: 888410-75-1
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: RRYHVIXOXLFFQR-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde 在 盐酸 、 silver(l) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 ((7R,9R)-2-(2,6-diisopropylphenyl)-8,8-dimethyl-1,2,6,7,8,9-hexahydro-7,9-methanoimidazo[1,5-a]quinolin-1-yl)copper(I) chloride
  参考文献：
  名称：

  Chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes and their copper complexes for asymmetric catalysis

  摘要：

  Novel chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes derived from beta-pinene have been developed. The preliminary studies with both the in situ generated and preformed copper-carbene complexes have shown these chiral NHCs are efficient and selective ligands in the Cu-catalyzed asymmetric conjugate borylation of alpha,beta-unsaturated esters. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.004
• 作为产物：
  描述：

  beta-pinene 在 1,1'-双(二苯基膦)二茂铁 、 氨 、 palladium diacetate 、 二异丁基氢化铝 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~140.0 ℃ 、1.2 MPa 条件下， 反应 43.0h， 生成 (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carbaldehyde
  参考文献：
  名称：

  Chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes and their copper complexes for asymmetric catalysis

  摘要：

  Novel chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes derived from beta-pinene have been developed. The preliminary studies with both the in situ generated and preformed copper-carbene complexes have shown these chiral NHCs are efficient and selective ligands in the Cu-catalyzed asymmetric conjugate borylation of alpha,beta-unsaturated esters. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.004

文献信息

• New pinene-derived pyridines as bidentate chiral ligands
  作者：Andrei V. Malkov、Angus J.P. Stewart-Liddon、Filip Teplý、Lukáš Kobr、Kenneth W. Muir、David Haigh、Pavel Kočovský

  DOI：10.1016/j.tet.2008.02.045

  日期：2008.4

  β-pinene 11. A copper complex of the pyridine–oxazoline ligands 8a has been found to catalyze asymmetric allylic oxidation of cyclic olefins 36a–c with good conversion rates and acceptable enantioselectivity (≤67% ee). The imidazolium salt 10 has been identified as a precursor of the corresponding N,N′-unsymmetrical N-heterocyclic carbene ligand, whose complex with palladium catalyzed the intramolecular

  从三氟甲磺酸酯14开始，已经开发了一种新的双齿吡啶8a – d，9和10的合成方法，而三氟甲磺酸酯14可以从β-pine烯11得到。已发现吡啶-恶唑啉配体8a的铜络合物可催化环烯烃36a - c的不对称烯丙基氧化，并具有良好的转化率和可接受的对映选择性（≤67％ee）。咪唑鎓盐10已被确定为相应的N，N'-不对称N的前体-杂环卡宾配体，其与钯的配合物催化分子内酰胺烯酸酯α-芳基化，从而以优异的收率但对映选择性低，生成了羟吲哚45。
• Chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes and their copper complexes for asymmetric catalysis
  作者：Jin-Long Zhang、Liang-An Chen、Rui-Bin Xu、Chuan-Fei Wang、Yuan-Ping Ruan、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2013.03.004

  日期：2013.4

  Novel chiral imidazo[1,5-a]tetrahydroquinoline N-heterocyclic carbenes derived from beta-pinene have been developed. The preliminary studies with both the in situ generated and preformed copper-carbene complexes have shown these chiral NHCs are efficient and selective ligands in the Cu-catalyzed asymmetric conjugate borylation of alpha,beta-unsaturated esters. (C) 2013 Elsevier Ltd. All rights reserved.