6,6'-(((1R,2R)-cyclohexane-1,2-diylbis(methylazanediyl))bis(methylene))bis(2,4-di-tert-butylphenol) | 914614-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,6'-(((1R,2R)-cyclohexane-1,2-diylbis(methylazanediyl))bis(methylene))bis(2,4-di-tert-butylphenol)
• 英文别名: (1R,2R)-N,N’-dimethyl-N,N’-di[(2-hydroxy-3,5-di-tert-butyl)benzyl]-1,2-diaminocyclohexane；(1R,2R)-N,N′-dimethyl-N,N′-di[(2-hydroxy-3,5-di(tert-butyl))benzyl]-1,2-diaminocyclohexane；(R,R)-HOC6H2(tert-butyl)2CH2N(Me)C6H10N(Me)CH2C6H2(tert-butyl)2OH；2,4-ditert-butyl-6-[[[(1R,2R)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl-methylamino]cyclohexyl]-methylamino]methyl]phenol
• CAS: 914614-75-8
• 化学式: C₃₈H₆₂N₂O₂
• 分子量: 578.922
• InChiKey: DPBLYEQWFHIGDT-ROJLCIKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6'-(((1R,2R)-cyclohexane-1,2-diylbis(methylazanediyl))bis(methylene))bis(2,4-di-tert-butylphenol) 、 copper(II) acetate monohydrate 以 乙醇 为溶剂， 反应 12.0h， 以85%的产率得到
  参考文献：
  名称：

  Effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward asymmetric nitroaldol reactions

  摘要：

  The synthesis and effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward nitroaldol reactions of nitromethane with various aldehydes have been described. The salan complexes exhibit superior results compared to the salalen and salalan complexes; the nature of the N,N-substituents is crucial for the enantioselectivity of the target nitroaldol products. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.07.013
• 作为产物：
  描述：

  聚合甲醛 、 (R,R)-N,N'-bis(3,5-di-tert-butylsalicyl)-1,2-diaminocyclohexane 在 sodium tetrahydroborate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 0.33h， 以94%的产率得到6,6'-(((1R,2R)-cyclohexane-1,2-diylbis(methylazanediyl))bis(methylene))bis(2,4-di-tert-butylphenol)
  参考文献：
  名称：

  手性salan配体的非对映体特异性锆配合物：1-己烯和4-甲基-1-戊烯的同种异体聚合和1,5-己二烯的环聚合。

  摘要：

  发现手性Salan配体以高度非对映选择性的方式包裹在锆周围，导致在金属上具有预定手性的C 2对称络合物。这些配合物导致高级烯烃的活性聚合，它们的活性和同种异构性的诱导，具体取决于酚盐取代基的性质。

  DOI：

  10.1021/ja0647654

文献信息

• Stereoselective protonation of 2-methyl-1-tetralone lithium enolate catalyzed by salan-type diamines
  作者：Daniel Łowicki、Justyna Watral、Maciej Jelecki、Wiktor Bohusz、Marcin Kwit

  DOI：10.1016/j.tet.2021.132085

  日期：2021.4

  Asymmetric protonation of ketone enolates is a convenient alternative to asymmetric alkylation of enolates that allows to convert racemic ketones into their optically active form. Here, we have reported an efficient enantioselective protonation of 2-methyl-1-tetralone lithium enolate catalyzed by salan-type diamines. A broad series of salan-type catalysts were synthesized, including several previously

  酮烯醇化物的不对称质子化是烯醇化物的不对称烷基化的便利替代方法，其允许将外消旋酮转化为它们的光学活性形式。在这里，我们报道了由Salan型二胺催化的2-甲基-1-四氢萘酮烯醇锂的有效对映选择性质子化。合成了一系列的萨兰型催化剂，包括几种以前未知的催化剂，随后在标题反应中进行了测试。用作有机催化剂的手性胺首次显示出比化学计量质子化剂更好的结果。仅10mol％的salan的施用允许以高收率和高达75％的对映体过量获得标题酮。DFT计算了催化剂及其与烯醇锂的配合物的结构，
• Achiral Tetrahydrosalen Ligands for the Synthesis of <i>C</i>₂-Symmetric Titanium Complexes:  A Structure and Diastereoselectivity Study
  作者：Jaume Balsells、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1021/ic010456x

  日期：2001.10.1

  Achiral tetrahydrosalen ligands have been employed in the synthesis of chiral C-2-symmetric titanium complexes. When combined with tetrahydrosalen ligands 2a and 2b, titanium tetraisopropoxide liberated 2 equiv of isopropyl alcohol and generated the (tetrahydrosalen)Ti(O-i-Pr)(2) complexes 3a and 3b. These complexes were shown to be C-2-symmetric by H-1 and C-13H-1} NMR spectrometry and X-ray crystallography. X-ray structures of 3a and 3b indicate that the bonding of the tetrahydrosalen ligand to titanium is different than the bonding of salen ligands to titanium. Whereas salen ligands usually bind to titanium in a planar arrangement, the tetrahydrosalen is bonded with the phenoxide oxygens mutually trans. When bound in this fashion, the nitrogens of the tetrahydrosalen ligand and the titanium become stereogenic centers. The use of titanium complexes of high enantiopurity in the generation of tetrahydrosalen titanium adducts resulted in a maximum diastereoselectivity of 2:1. The diastereoselectivity obtained using chiral titanium alkoxide complexes was greater than the diastereoselectivity observed when a tetrahydrosalen ligand derived from (SS)-trans-diaminocyclohexane was employed.
• Diastereomerically-Specific Zirconium Complexes of Chiral Salan Ligands:  Isospecific Polymerization of 1-Hexene and 4-Methyl-1-pentene and Cyclopolymerization of 1,5-Hexadiene
  作者：Adi Yeori、Israel Goldberg、Michael Shuster、Moshe Kol

  DOI：10.1021/ja0647654

  日期：2006.10.1

  Chiral Salan ligands were found to wrap in a highly diastereoselective manner around zirconium leading to C2-symmetric complexes of predetermined chirality at the metal. These complexes led to active polymerization of higher olefins, their activity and isospecific induction depending on the nature of the phenolate substituents.

  发现手性Salan配体以高度非对映选择性的方式包裹在锆周围，导致在金属上具有预定手性的C 2对称络合物。这些配合物导致高级烯烃的活性聚合，它们的活性和同种异构性的诱导，具体取决于酚盐取代基的性质。
• Effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward asymmetric nitroaldol reactions
  作者：Masanam Kannan、Tharmalingam Punniyamurthy

  DOI：10.1016/j.tetasy.2014.07.013

  日期：2014.10

  The synthesis and effect of ligand N,N-substituents on the reactivity of chiral copper(II) salalen, salan, and salalan complexes toward nitroaldol reactions of nitromethane with various aldehydes have been described. The salan complexes exhibit superior results compared to the salalen and salalan complexes; the nature of the N,N-substituents is crucial for the enantioselectivity of the target nitroaldol products. (C) 2014 Elsevier Ltd. All rights reserved.