N¹-monobenzyl,N²-Boc-(1R,2R)-diaminocyclohexane | 1354486-21-7

• 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: N¹-monobenzyl,N²-Boc-(1R,2R)-diaminocyclohexane
• 英文别名: (R,R)-N-benzyl-N’-tert-butoxylcarbonyl-1,2-diaminocyclohexane；Tert-butyl (1R,2R)-2-(benzylamino)-cyclohexylcarbamate；tert-butyl N-[(1R,2R)-2-(benzylamino)cyclohexyl]carbamate
• CAS: 1354486-21-7
• 化学式: C₁₈H₂₈N₂O₂
• 分子量: 304.433
• InChiKey: MTFCVOVRLIBVAP-HZPDHXFCSA-N

物化性质

• 沸点：
  435.4±34.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-monobenzyl,N²-Boc-(1R,2R)-diaminocyclohexane 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 (1R,2R)-N1-苄基环己烷-1,2-二胺
  参考文献：
  名称：

  A chiral primary-tertiary-1,2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions

  摘要：

  A novel chiral 1,2-diaminocyclohexane derivative, (1R,2R)-N-1-n-pentyl, N-1-benzyl-1,2-cyclohexanediamine, was designed, synthesized and applied as a catalyst in a number of aldol reactions between ketones and aryl aldehydes. Reactions between acetone and aryl aldehydes gave aldol products with moderate to good yields and with excellent enantioselectivity (up to yield 85%, ee 98%), while reactions between cyclohexanone and aryl aldehydes provided anti-beta-hydroxyketone products with excellent yields, diastereoselectivity and with enantioselectivity (up to 82% yield, anti/syn ratio 99:1, ee 99%). The aldol reactions between acetone and isatins were investigated, which afforded excellent yields and enantioselectivity (up to 95% yield, 98% ee). The (R)- and (S)-isomers of convolutamydine A were obtained with 95% yield and 96% ee, and 95% yield and 94% ee, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.026
• 作为产物：
  描述：

  苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N¹-monobenzyl,N²-Boc-(1R,2R)-diaminocyclohexane
  参考文献：
  名称：

  通过空间受阻的铂（II）配合物来克服对顺铂的耐药性。

  摘要：

  设计并制备了许多衍生自（1R，2R）-N1-苄基环己烷-1,2-二胺衍生物的具有位阻的铂（II）配合物。生物学分析表明，大多数复合物均对测试的癌细胞系具有抗肿瘤活性，尤其是那些带有氯离子的癌细胞，因为离去基团与顺铂和奥沙利铂具有相容性或更高的活性。络合物2a是最有效的药物，对顺铂耐药的SGC7901 / CDDP癌细胞系也敏感，随后已通过细胞摄取，流式细胞仪，凝胶电泳和Western blot分析对其进行了研究。由配体的未决2-氟苄基部分引起的空间位阻可能是其克服顺铂耐药细胞的能力的关键因素。

  DOI：

  10.1016/j.ejmech.2016.02.060

文献信息

• Application of Ruthenium Complexes of Triazole-Containing Tridentate Ligands to Asymmetric Transfer Hydrogenation of Ketones
  作者：Tarn C. Johnson、William G. Totty、Martin Wills

  DOI：10.1021/ol302354z

  日期：2012.10.19

  The synthesis of a series of tridentate ligands based on a homochiral 1,2-diamine structure attached to a triazole group and their subsequent applications to the asymmetric transfer hydrogenation of ketones are described. In the best cases, alcohols of up to 93% ee were obtained. Although base is not required, the use of Ru3(CO)12 as metal source is essential, indicating a unique mechanism for the

  描述了基于与三唑基连接的同手性1,2-二胺结构的一系列三齿配体的合成及其在酮的不对称转移氢化中的后续应用。在最佳情况下，获得的酒精含量高达ee的93％。尽管不需要碱，但是必须使用Ru 3（CO）12作为金属源，这表明形成活性催化剂的独特机理。
• Highly stereoselective direct aldol reactions catalyzed by a bifunctional chiral diamine
  作者：Lei Li、Shaohua Gou、Fei Liu

  DOI：10.1016/j.tetasy.2013.11.017

  日期：2014.1

  The enantioselective organocatalytic direct aldol reactions of ketones with various aldehydes were developed by using chiral 1,2-cyclohexanediamine COACH) based multifunctional ligands via a noncovalent catalysis mechanism. By using a catalyst, we also obtained functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields and with good to excellent enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.
• A chiral primary-tertiary-1,2-diamine as an efficient catalyst in asymmetric aldehyde–ketone or ketone–ketone aldol reactions
  作者：Biao Xu、Lei Li、Shaohua Gou

  DOI：10.1016/j.tetasy.2013.09.026

  日期：2013.12

  A novel chiral 1,2-diaminocyclohexane derivative, (1R,2R)-N-1-n-pentyl, N-1-benzyl-1,2-cyclohexanediamine, was designed, synthesized and applied as a catalyst in a number of aldol reactions between ketones and aryl aldehydes. Reactions between acetone and aryl aldehydes gave aldol products with moderate to good yields and with excellent enantioselectivity (up to yield 85%, ee 98%), while reactions between cyclohexanone and aryl aldehydes provided anti-beta-hydroxyketone products with excellent yields, diastereoselectivity and with enantioselectivity (up to 82% yield, anti/syn ratio 99:1, ee 99%). The aldol reactions between acetone and isatins were investigated, which afforded excellent yields and enantioselectivity (up to 95% yield, 98% ee). The (R)- and (S)-isomers of convolutamydine A were obtained with 95% yield and 96% ee, and 95% yield and 94% ee, respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• Toward overcoming cisplatin resistance via sterically hindered platinum(II) complexes
  作者：Haiyan Yu、Shaohua Gou、Zhimei Wang、Feihong Chen、Lei Fang

  DOI：10.1016/j.ejmech.2016.02.060

  日期：2016.5

  number of platinum(II) complexes with steric hindrance derived from (1R,2R)-N1-benzylcyclohexane-1,2-diamine derivatives were designed and prepared. Biological assay indicated that most complexes showed antitumor activity against the tested cancer cell lines, especially those with chloride anions as leaving groups had compatible or superior activity to cisplatin and oxaliplatin. Complex 2a, as the most

  设计并制备了许多衍生自（1R，2R）-N1-苄基环己烷-1,2-二胺衍生物的具有位阻的铂（II）配合物。生物学分析表明，大多数复合物均对测试的癌细胞系具有抗肿瘤活性，尤其是那些带有氯离子的癌细胞，因为离去基团与顺铂和奥沙利铂具有相容性或更高的活性。络合物2a是最有效的药物，对顺铂耐药的SGC7901 / CDDP癌细胞系也敏感，随后已通过细胞摄取，流式细胞仪，凝胶电泳和Western blot分析对其进行了研究。由配体的未决2-氟苄基部分引起的空间位阻可能是其克服顺铂耐药细胞的能力的关键因素。