(1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane
• 英文别名: (1R,2R)-N1,N2-Bis(anthracen-9-ylmethyl)cyclohexane-1,2-diamine；(1R,2R)-1-N,2-N-bis(anthracen-9-ylmethyl)cyclohexane-1,2-diamine
• 化学式: C₃₆H₃₄N₂
• 分子量: 494.679
• InChiKey: ZKZMLJPVYBGYPL-LQFQNGICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  甲乙酐 、 (1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1R,2R)-N,N'-bis(9-anthracenylmethyl)-N,N'-bisformyl-1,2-cyclohexanediamine
  参考文献：
  名称：

  手性双甲酰胺型有机催化剂催化芳香醛与烯丙基三氯硅烷的不对称烯丙基化反应

  摘要：

  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％。

  DOI：

  10.1016/j.tetasy.2012.02.015
• 作为产物：
  描述：

  trans-N,N'-bis(anthracen-9-ylmethylidene)cyclohexane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 (1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane
  参考文献：
  名称：

  手性双甲酰胺型有机催化剂催化芳香醛与烯丙基三氯硅烷的不对称烯丙基化反应

  摘要：

  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％。

  DOI：

  10.1016/j.tetasy.2012.02.015
• 作为试剂：
  描述：

  2-硝基乙醇 、 正己醛 在 copper(II) acetate monohydrate 、 (1R,2R)-N,N'-di(anthracenyl-9'-methylene)-1,2-diaminocyclohexane 、 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 反应 70.25h， 生成 (2S,3S)-2-nitro-5-phenyl-1,3-pentanediol 、 (2R,3S)-2-nitro-5-phenylpentan-1,3-diol
  参考文献：
  名称：

  Asymmetric nitroaldol reaction catalyzed by copper–diamine complexes: selective construction of two contiguous stereogenic centers

  摘要：

  Chiral copper(II) complexes of secondary bisamines derived from 1,2-diaminocyclohexane were successfully used in the diastereoselective nitroaldol reaction. The reactions were carried out in the presence of 10 mol % of the Cu(II) complex and 7.7 mol % of i-Pr2NEt in 2-propanol at -30 degrees C. Good to excellent yields, enantioselectivities of up to 99%, and moderate to excellent diastereoselectivities were obtained for both aromatic or aliphatic aldehydes and various prochiral nitrocompounds forming the corresponding beta-nitroalcohols with two contiguous stereocenters. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.001

文献信息

• trans-1,3-Bis(Anthracen-9-Ylmethyl)Octahydro-Benzimidazoles: Synthesis and Study of Spectral Properties
  作者：I. E. Tolpygin、K. S. Tihomirova、O. S. Popova、O. G. Nikolaeva、Yu. V. Revinskii、A. D. Dubonosov、V. A. Bren

  DOI：10.1007/s10593-014-1446-y

  日期：2014.4

  The reaction between (+/-)-trans-cyclohexane-1,2-diamine and anthracene-9-carbaldehyde with a subsequent reduction of the condensation product gave N,N'-bis(anthracen-9-ylmethyl)cyclohexane-1,2-diamine. The interaction of this diamine with aldehydes was shown to produce octahydrobenz-imidazoles. The chemosensor properties of the obtained compounds were investigated, and a high affinity to Zn2+ cations was identified.
• Chiral hybrid silica: sol–gel heterogenisation of trans-(1R,2R)-diaminocyclohexane ligands for the rhodium catalysed enantioselective reduction of acetophenone
  作者：Anne Brethon、Joël J.E Moreau、Michel Wong Chi Man

  DOI：10.1016/j.tetasy.2003.11.005

  日期：2004.2

  The synthesis of derivatives of trans-(1R,2R)-diaminocyclohexane with different substituents on the nitrogen atoms has been achieved. Rhodium complexes of these chiral ligands were evaluated as homogeneous catalysts for the asymmetric hydride transfer reduction (HTR) of acetophenone leading to moderate selectivities (ee = 0-57%). The silylation of a bromo-aryl derivative was successfully performed by a Heck's coupling reaction with vinyltriethoxysilane in the presence of a palladium catalyst. The immobilisation of this catalyst was then achieved by the sol-gel hydrolysis condensation. The resulting hybrid catalytic materials showed moderate selectivity, although much higher than the related homogeneous catalytic species. (C) 2003 Elsevier Ltd. All rights reserved.