(1R,2R)-N,N'-bis[(1-naphthyl)-methyl]-1,2-diaminocyclohexane

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2R)-N,N'-bis[(1-naphthyl)-methyl]-1,2-diaminocyclohexane
• 英文别名: (1R,2R)-N1,N2-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine；(R,R)-N,N’-bis(1-naphthylmethyl)cyclohexane-1,2-diamine；(R,R)-1,2-di(1-naphthyl-CH2NH)cyclohexane；(1R,2R)-1-N,2-N-bis(naphthalen-1-ylmethyl)cyclohexane-1,2-diamine
• 化学式: C₂₈H₃₀N₂
• 分子量: 394.56
• InChiKey: MOFAWJAXQCZGDZ-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N,N'-bis[(1-naphthyl)-methyl]-1,2-diaminocyclohexane 在 三乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 N,N'-di-(1-naphthylmethylene)-1,2-cyclohexyldiamino N-phosphonylchloride
  参考文献：
  名称：

  Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups

  摘要：

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.

  DOI：

  10.3987/com-14-s(k)25
• 作为产物：
  描述：

  (1R,2R)-bis-1-naphthyliminocyclohexane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以88%的产率得到(1R,2R)-N,N'-bis[(1-naphthyl)-methyl]-1,2-diaminocyclohexane
  参考文献：
  名称：

  N-杂环卡宾介导的苯酚对不对称烷基芳基烯酮的对映选择性加成

  摘要：

  手性N-杂环卡宾（NHC）介导将2-苯基苯酚对映选择性加成到不对称的烷基芳基烯酮中，从而提供具有良好对映体控制水平的ee-烷基-α-芳酸衍生物（最高ee达84％）。在NHC促进的酯化反应中使用2-苯基苯酚和二氢苯酚，使用衍生自焦谷氨酸的三唑鎓预催化剂观察到对映体立体化学结果，这与这些过程中起作用的独特机理相符。

  DOI：

  10.1002/adsc.200900538

文献信息

• Asymmetric allylation reactions of aromatic aldehydes with allyltrichlorosilane catalyzed by chiral bisformamide-type organocatalysts
  作者：Yuya Tanimura、Kaori Ishimaru

  DOI：10.1016/j.tetasy.2012.02.015

  日期：2012.3

  Asymmetric allylation reactions of aromatic aldehydes with allyltrichlorosilane were catalyzed by C2-symmetrical chiral bisformamides in the presence of potassium carbonate and potassium phosphate, to afford the corresponding homoallylic alcohols in excellent yields with up to 83% ee.

  在碳酸钾和磷酸钾存在下，C 2对称手性双甲酰胺催化芳族醛与烯丙基三氯硅烷的不对称烯丙基化反应，从而以极高的收率得到相应的均烯丙基醇，ee最高可达83％。
• Highly selective R,S-coordination of non racemic (1R,2R)-(1,2-dialkyl)-1,2-diamine cyclohexane derivatives to palladium dichloride
  作者：Esfandiar Rafii、Benjamin Dassonneville、Andreas Heumann

  DOI：10.1039/b613961b

  日期：——

  In non-racemic (1R,2R)-(1,2-dialkyl)-1,2-diaminocyclohexane palladium dichloride complexes the C2 symmetry of the diamine ligand is broken, resulting in selective R,S-coordination.

  在非外消旋的（1R，2R）-（1,2-二烷基）-1,2-二氨基环己烷二氯化钯配合物中，二胺配体的C2对称性被破坏，导致选择性的R，S配位。
• Synthesis of N,N′-Dialkylated Cyclohexane-1,2-diamines and Their Application as Asymmetric Ligands and Organocatalysts for the Synthesis of Alcohols
  作者：Denis Chusov、Alexey Tsygankov、Man-Seog Chun、Alexandra Samoylova、Seongyeon Kwon、Yuliya Kreschenova、Suhyeon Kim、Euijin Shin、Jinho Oh、Tatyana Strelkova、Valerii Kolesov、Fedor Zubkov、Sergei Semenov、Ivan Fedyanin

  DOI：10.1055/s-0036-1588382

  日期：——

  A series of N,N′-dialkylated derivatives of (1R,2R)-cyclohexane-1,2-diamine were synthesized, and a new approach to the one-pot preparation of this type of amine was demonstrated. The prepared diamines were used as organocatalysts for the two-step synthesis of α-hydroxy γ-keto esters from arenes, chlorooxoacetates, and ketones; they were also used as chiral ligands for Meervein–Ponndorf–Verley reductions

  合成了一系列(1R,2R)-环己烷-1,2-二胺的N,N'-二烷基化衍生物，并展示了该类胺的一锅法制备新方法。制备的二胺用作有机催化剂，用于从芳烃、氯代乙酸酯和酮两步合成α-羟基γ-酮酯；它们也被用作 Meervein-Ponndorf-Verley 还原和亨利反应的手性配体。
• HFIP‐Promoted Substitution in the Ferrocene Series: Smooth Approach towards Original Catalysts**
  作者：William Erb、Victor Carré、Thierry Roisnel

  DOI：10.1002/ejoc.202100824

  日期：2021.11.8

  Pseudo-benzylic substitution promoted by fluorinated solvent from various iodoferrocenes is described. These new reaction conditions allow the fast generation of libraries of derivatives for applications in catalysis for example, as demonstrated with the synthesis of original ligands used in cross-coupling reactions.

  描述了由来自各种碘二茂铁的氟化溶剂促进的伪苄基取代。这些新的反应条件允许快速生成用于催化应用的衍生物库，例如，如交叉偶联反应中使用的原始配体的合成所证明的那样。
• Nickel-Catalyzed Asymmetric <i>C</i>-Alkylation of Nitroalkanes: Synthesis of Enantioenriched β-Nitroamides
  作者：Vijayarajan Devannah、Rajgopal Sharma、Donald A. Watson

  DOI：10.1021/jacs.9b04175

  日期：2019.5.29

  A general catalytic method for asymmetric C-alkylation of nitroalkanes using nickel catalysis is described. This method enables the formation of highly enantioenriched β-nitroamides from readily available α-bromoamides using mild reaction conditions that are compatible with a wide range of functional groups. When combined with subsequent reactions, this method allows access to highly enantioenriched

  描述了使用镍催化对硝基烷烃进行不对称 C-烷基化的一般催化方法。该方法能够使用与各种官能团兼容的温和反应条件，从容易获得的 α-溴酰胺形成高度对映体富集的 β-硝基酰胺。当与后续反应相结合时，该方法允许获得具有含氮完全取代的碳中心的高度对映体富集的产品。