(6R,8R)-methyl 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carboxylate | 1027754-34-2

• 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)-methyl 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carboxylate
• CAS: 1027754-34-2
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: YCPLVTBINBBCEY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6R,8R)-methyl 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以67%的产率得到((6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinolin-2-yl)methanol
  参考文献：
  名称：

  新的pin烯衍生的吡啶作为二齿手性配体

  摘要：

  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。

  DOI：

  10.1016/j.tet.2008.02.045
• 作为产物：
  描述：

  (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinolin-2(1H)-one 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 (6R,8R)-methyl 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinoline-2-carboxylate
  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

• Preparation of chiral ruthenium(iv) complexes and applications in regio- and enantioselective allylation of phenols
  作者：Zeyneb Sahli、Nolwenn Derrien、Simon Pascal、Bernard Demerseman、Thierry Roisnel、Frédéric Barrière、Mathieu Achard、Christian Bruneau

  DOI：10.1039/c0dt01812k

  日期：——

  Facile preparations of chiral [Ru(Cp*)]- and [Ru(Cp′)]-based allyl complexes featuring N,O chelate derived from (+)-nopinone are described. Single crystal X-ray structural analysis of one complex revealed the preferential configuration of the ruthenium centre and the orientation of the unsymmetrical allylic substituent. Applications of these complexes in catalysis for nucleophilic allylic substitution

  描述了基于[Ru（Cp *）]和[Ru（Cp'）]的手性烯丙基复合物的简便制备方法，这些复合物的特征是衍生自（+）-去皮酮的N，O螯合物。一种配合物的单晶X射线结构分析显示了钌中心的优先构型和不对称烯丙基取代基的取向。这些络合物在亲核烯丙基取代的催化中的应用使得可以从苯酚区域和对映选择性地形成支链烯丙基醚。
• Controlling Helix Sense at N- and C-Termini in Quinoline Oligoamide Foldamers by β-Pinene-Derived Pyridyl Moieties
  作者：Lu Zheng、Yulin Zhan、Chengyuan Yu、Fu Huang、Ying Wang、Hua Jiang

  DOI：10.1021/acs.orglett.7b00510

  日期：2017.3.17

  A series of quinoline oligoamide foldamers bearing a beta-pinene-derived pyridyl group at the N-terminus or the C terminus were synthesized, and the efficiencies of chiral inductions have been evaluated by H-1 NMR and CD spectra. The chiral inductions were quantitative when chiral pyridyl acid was appended at the N-terminus, but were inferior when chiral pyridyl amine was appended at the C-terminus. Unexpectedly, N-oxidation on the pyridine ring at the C-terminus does not notably enhance the chiral induction efficiency in spite of the presence of three-center hydrogen bonds.