(1R,2R)-N¹-cyclopentyl-1,2-cyclohexanediamine | 1258827-39-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R)-N¹-cyclopentyl-1,2-cyclohexanediamine
• 英文别名: (1R,2R)-N¹-cyclopentylcyclohexane-1,2-diamine；(1R,2R)-2-N-cyclopentylcyclohexane-1,2-diamine
• CAS: 1258827-39-2
• 化学式: C₁₁H₂₂N₂
• 分子量: 182.309
• InChiKey: KSKBQJRQWJDWJG-GHMZBOCLSA-N

物化性质

• 沸点：
  262.7±8.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N¹-cyclopentyl-1,2-cyclohexanediamine 以 水 为溶剂， 反应 42.0h， 生成 cis-[(1R,2R)-N¹-cyclopentyl-1,2-diaminocyclohexane-N,N’][(+)-camphorato-O,O’]platinum(II)
  参考文献：
  名称：

  Synthesis and biological evaluation of platinum(II) complexes containing (1R,2R)-N1-alkyl-1,2-diaminocyclohexane and D-(+)-camphorate ligands

  摘要：

  Five platinum(II) complexes with N-monoalkyl derivatives of 1R,2R-diaminocyclohexane as ligands and D-(+)-camphorate anion as leaving group have been synthesized and characterized by elemental analysis, IR, H-1 NMR, ESI-MS, and HRMS spectra. All complexes were evaluated for their in vitro cytotoxicity against four human tumor cell lines and most of them showed promising cytotoxic activity, especially compounds 3 and 4 with branched alkyl substituent at one of nitrogen atoms. Preliminary mechanism study by flow cytometry and agarose gel electrophoresis was also carried out in comparison with cisplatin and oxaliplatin. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.011
• 作为产物：
  描述：

  (1R,2R)-反式-N-Boc-1,2-二氨基环己烷 在 盐酸 、 sodium sulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 14.5h， 生成 (1R,2R)-N¹-cyclopentyl-1,2-cyclohexanediamine
  参考文献：
  名称：

  Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products

  摘要：

  Chiral derivatives of trans-1,2-diaminocyclohexane with different N,N-dialkyl groups in well-defined orientations have been synthesized, and applied as catalysts for the asymmetric aldol reaction between a variety of aldehydes and ketones. Enantiomeric catalyst 1j catalyzed the reaction in ethanol and provided excellent diastereoselectivity and enantioselectivity. Significantly, simple replacement of organic solvents with water switched the products of the aldol reactions from anti to syn configuration. Such catalytic reactions led to the products with anti to syn diastereoselectivity up to 99:1 in ethanol, while in water gave the products with syn to anti diastereoselectivity up to 99:1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.053
• 作为试剂：
  描述：

  对硝基苯甲醛 、 环己酮 在 (1R,2R)-N¹-cyclopentyl-1,2-cyclohexanediamine 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 24.08h， 以23%的产率得到
  参考文献：
  名称：

  Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products

  摘要：

  Chiral derivatives of trans-1,2-diaminocyclohexane with different N,N-dialkyl groups in well-defined orientations have been synthesized, and applied as catalysts for the asymmetric aldol reaction between a variety of aldehydes and ketones. Enantiomeric catalyst 1j catalyzed the reaction in ethanol and provided excellent diastereoselectivity and enantioselectivity. Significantly, simple replacement of organic solvents with water switched the products of the aldol reactions from anti to syn configuration. Such catalytic reactions led to the products with anti to syn diastereoselectivity up to 99:1 in ethanol, while in water gave the products with syn to anti diastereoselectivity up to 99:1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.053

文献信息

• Study on the cytotoxic activity of platinum(II) complexes of (1 R ,2 R )- N 1 -cyclopentyl-1,2-cyclohexanediamine with substituted malonate derivatives
  作者：Zhiping Zhou、Feihong Chen、Gang Xu、Shaohua Gou

  DOI：10.1016/j.bmcl.2015.12.019

  日期：2016.1

  Three platinum(II) complexes of (1R,2R)-N(1)-cyclopentyl-1,2-cyclohexanediamine with malonate derivatives were designed, synthesized and spectrally characterized. MTT assay showed that the complexes possessed positive cytotoxic effect on the four human solid tumor cell lines. Among the complexes, complex 2 demonstrated the strongest cytotoxic activity compared to cisplatin and oxaliplatin against HepG2

  设计，合成和光谱表征了（1R，2R）-N（1）-环戊基-1,2-环己二胺与丙二酸酯衍生物的三种铂（II）配合物。MTT分析表明，该复合物对四种人实体瘤细胞系具有积极的细胞毒性作用。在复合物中，与顺铂和奥沙利铂相比，复合物2对HepG2细胞系表现出最强的细胞毒活性（IC50 =3.04μM）。此外，凝胶电泳的结果表明复合物2以不同于顺铂的模式与DNA相互作用。细胞增殖抑制和细胞摄取的机理研究表明，复合物2比顺铂更有效地进入HepG2细胞，表现出大量G2积累，然后诱导细胞凋亡。
• Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products
  作者：Lei Li、Shaohua Gou、Fei Liu

  DOI：10.1016/j.tetlet.2013.09.053

  日期：2013.11

  Chiral derivatives of trans-1,2-diaminocyclohexane with different N,N-dialkyl groups in well-defined orientations have been synthesized, and applied as catalysts for the asymmetric aldol reaction between a variety of aldehydes and ketones. Enantiomeric catalyst 1j catalyzed the reaction in ethanol and provided excellent diastereoselectivity and enantioselectivity. Significantly, simple replacement of organic solvents with water switched the products of the aldol reactions from anti to syn configuration. Such catalytic reactions led to the products with anti to syn diastereoselectivity up to 99:1 in ethanol, while in water gave the products with syn to anti diastereoselectivity up to 99:1. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of platinum(II) complexes containing (1R,2R)-N1-alkyl-1,2-diaminocyclohexane and D-(+)-camphorate ligands
  作者：Yanyan Sun、Gang Xu、Zhe Cao、Shaohua Gou

  DOI：10.1016/j.ica.2012.10.011

  日期：2013.1

  Five platinum(II) complexes with N-monoalkyl derivatives of 1R,2R-diaminocyclohexane as ligands and D-(+)-camphorate anion as leaving group have been synthesized and characterized by elemental analysis, IR, H-1 NMR, ESI-MS, and HRMS spectra. All complexes were evaluated for their in vitro cytotoxicity against four human tumor cell lines and most of them showed promising cytotoxic activity, especially compounds 3 and 4 with branched alkyl substituent at one of nitrogen atoms. Preliminary mechanism study by flow cytometry and agarose gel electrophoresis was also carried out in comparison with cisplatin and oxaliplatin. (C) 2012 Elsevier B. V. All rights reserved.