2,2-bis[(5S,7S)-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinolin-2-yl]propane | 502852-27-9

• 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: 2,2-bis[(5S,7S)-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinolin-2-yl]propane
• 英文别名: 2,2'-(propane-2,2-diyl)bis(6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline)；(1S,9S)-5-[2-[(1S,9S)-10,10-dimethyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-5-yl]propan-2-yl]-10,10-dimethyl-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-triene
• CAS: 502852-27-9
• 化学式: C₂₇H₃₄N₂
• 分子量: 386.58
• InChiKey: JBFOQWVENSUEGM-XAMWDVODSA-N

物化性质

• 熔点：
  161 °C
• 沸点：
  474.4±40.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-bis[(5S,7S)-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinolin-2-yl]propane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以79%的产率得到2,2-bis[(5S,7S)-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinolin-2-yl]propane N,N'-dioxide
  参考文献：
  名称：

  新型手性二吡啶基甲烷N-氧化物促进醛与烯丙基三氯硅烷的对映选择性烯丙基化

  摘要：

  已经从天然存在的单萜制备了新的手性二吡啶N-一氧化物和N，N'-二氧化物，其在两个吡啶环之间具有异丙叉骨架。在烯丙基三氯硅烷对醛的对映选择性加成中已证明了它们作为有机催化剂的用途。获得了高达85％ee的对映选择性。

  DOI：

  10.1016/j.tetlet.2007.04.028
• 作为产物：
  描述：

  在 乙酸铵 、 溶剂黄146 作用下， 反应 3.0h， 以1.08 g的产率得到2,2-bis[(5S,7S)-5,7-methano-6,6-dimethyl-5,6,7,8-tetrahydroquinolin-2-yl]propane
  参考文献：
  名称：

  Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane

  摘要：

  The synthesis of enantiomerically pure C-2-symmetric dipyridylmethane ligands and related N,N'-dioxides is reported. A procedure for the synthesis of a few new enantiomerically pure C-2-symmetric pyridine N-oxides and the preparation of four pyridine N-oxides with oxygen and nitrogen atoms as further coordinating elements in the heterocycle framework is described. All compounds were prepared from naturally occurring monoterpenes. These new compounds were assessed as organocatalysts in two different reactions, namely the allylation of aldehydes with allyltrichlorosilane that afforded homoallylic alcohols in good yields and up to 85% ee and the stilbene oxide opening by the addition of tetrachlorosilane that gave chlorohydrin in quantitative yield and up to 70% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.105

文献信息

• Enantioselective allylation of aldehydes with allyltrichlorosilane promoted by new chiral dipyridylmethane N-oxides
  作者：Giorgio Chelucci、Nicola Belmonte、Maurizio Benaglia、Luca Pignataro

  DOI：10.1016/j.tetlet.2007.04.028

  日期：2007.6

  New chiral dipyridine N-monoxides and N,N′-dioxides, which possess an isopropylidene backbone between two pyridine rings, have been prepared from naturally occurring monoterpenes. Their utility as organocatalysts has been demonstrated in the enantioselective addition of allyltrichlorosilane to aldehydes. Enantioselectivities up to 85% ee have been obtained.

  已经从天然存在的单萜制备了新的手性二吡啶N-一氧化物和N，N'-二氧化物，其在两个吡啶环之间具有异丙叉骨架。在烯丙基三氯硅烷对醛的对映选择性加成中已证明了它们作为有机催化剂的用途。获得了高达85％ee的对映选择性。
• Novel C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands: synthesis and application in asymmetric diethylzinc addition to aldehydes
  作者：Yi-Shan Shih、Ramalingam Boobalan、Chinpiao Chen、Gene-Hsian Lee

  DOI：10.1016/j.tetasy.2013.12.020

  日期：2014.2

  C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands is described. The Mukaiyama–Michael reaction was applied as an important reaction for the synthesis of 2,2-bipyridylpropane 9. Among the ligands synthesized, ligand 11 exhibits excellent chiral induction (up to 97% ee) in diethylzinc addition to various aldehydes. The use of additional Lewis acid such as Ti(OiPr)4 in diethylzinc addition

  描述了C 2对称的手性O，N，N，O-四齿2,2-联吡啶二醇二醇丙烷配体的合成。Mukaiyama–Michael反应被用作合成2，2-联吡啶丙烷9的重要反应。在合成的配体中，配体11在二乙基锌和各种醛类化合物中均表现出出色的手性诱导（至多97％ee）。对于本催化体系，不需要在二乙基锌加成反应中使用额外的路易斯酸，例如Ti（O i Pr）4。
• Design of a new class of chiral C 2 -symmetric dipyridylmethane ligands and their application in asymmetric catalysis
  作者：Giorgio Chelucci、Giovanni Loriga、Gabriele Murineddu、Gerard A. Pinna

  DOI：10.1016/s0040-4039(02)02066-x

  日期：2002.11

  A new class of chiral C2-symmetric dipyridylmethane ligands was prepared from naturally occurring monoterpenes, according to a method based on a double Michael–azaannellation–aromatization sequence. These ligands were assessed in the enantioselective palladium-catalyzed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethylmalonate and in the copper-catalyzed cyclopropanation of styrene

  根据基于双迈克尔-氮杂退火-芳构化序列的方法，从天然单萜中制备了一类新的手性C 2对称二吡啶基甲烷配体。这些配体在1，3-二苯基丙-2-烯基乙酸酯与丙二酸二甲酯的对映选择性钯催化的烯丙基烷基化反应中以及在苯乙烯与重氮乙酸乙酯的铜催化的环丙烷化中评价这些配体。获得高达88％ee的对映选择性。
• Chiral pyridine N-oxides derived from monoterpenes as organocatalysts for stereoselective reactions with allyltrichlorosilane and tetrachlorosilane
  作者：Giorgio Chelucci、Salvatore Baldino、Gerard A. Pinna、Maurizio Benaglia、Laura Buffa、Stefania Guizzetti

  DOI：10.1016/j.tet.2008.05.105

  日期：2008.8

  The synthesis of enantiomerically pure C-2-symmetric dipyridylmethane ligands and related N,N'-dioxides is reported. A procedure for the synthesis of a few new enantiomerically pure C-2-symmetric pyridine N-oxides and the preparation of four pyridine N-oxides with oxygen and nitrogen atoms as further coordinating elements in the heterocycle framework is described. All compounds were prepared from naturally occurring monoterpenes. These new compounds were assessed as organocatalysts in two different reactions, namely the allylation of aldehydes with allyltrichlorosilane that afforded homoallylic alcohols in good yields and up to 85% ee and the stilbene oxide opening by the addition of tetrachlorosilane that gave chlorohydrin in quantitative yield and up to 70% ee. (C) 2008 Elsevier Ltd. All rights reserved.