(2S)-N¹-cyclohexyl-3-methyl-1,2-butanediamine | 473998-89-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-N¹-cyclohexyl-3-methyl-1,2-butanediamine
• 英文别名: (S)-1N-cyclohexyl-3-methylbutane-1,2-diamine；(2S)-1-N-cyclohexyl-3-methylbutane-1,2-diamine
• CAS: 473998-89-9
• 化学式: C₁₁H₂₄N₂
• 分子量: 184.325
• InChiKey: PAMXYMCWEDKUIK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• 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：

  2-羧基-3,4-二甲氧基苯甲醛 、 (2S)-N¹-cyclohexyl-3-methyl-1,2-butanediamine 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以83%的产率得到(3S,9bS)-1-cyclohexyl-3-isopropyl-6,7-dimethoxy-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Stereoselective syntheses of chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones

  摘要：

  Chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones 11a-11f, 14b.14c and 17a,b were prepared in 78-93% yields with high stereoselectivities (d.e. >99%) by the intermolecular condensations of 2-formylbenzoic acids 10 or 13 or 2-acetylbenzoic acid 15 with chiral diamines 9a-9f and 9h. Compounds 9a-9f and 9h were readily prepared in three steps from optically active N-Boc-alpha-amino acids 5a-5d. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00220-3
• 作为产物：
  描述：

  tert-butyl (S)-(1-(cyclohexylamino)-3-methyl-1-oxobutan-2-yl)carbamate 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S)-N¹-cyclohexyl-3-methyl-1,2-butanediamine
  参考文献：
  名称：

  Asymmetric hydroamination catalyzed by in situ generated chiral amidate and ureate complexes of zirconium — Probing the role of the tether in ligand design

  摘要：

  简单手性前体已经从廉价的手性起始物质合成。这些酰胺和脲配体支持锆配合物，成功催化了高达26%的内分子氢胺化反应。强调和讨论了成功配体设计所需的几个要素。特别是，通过多齿联结配体严格控制金属几何构型被确定为未来配体开发的一个关键方面。

  DOI：

  10.1139/v11-091

文献信息

• Stereoselective syntheses of chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones
  作者：Alan R. Katritzky、Hai-Ying He、Akhilesh K. Verma

  DOI：10.1016/s0957-4166(02)00220-3

  日期：2002.6

  Chiral (3S,9bS)-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones 11a-11f, 14b.14c and 17a,b were prepared in 78-93% yields with high stereoselectivities (d.e. >99%) by the intermolecular condensations of 2-formylbenzoic acids 10 or 13 or 2-acetylbenzoic acid 15 with chiral diamines 9a-9f and 9h. Compounds 9a-9f and 9h were readily prepared in three steps from optically active N-Boc-alpha-amino acids 5a-5d. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric hydroamination catalyzed by in situ generated chiral amidate and ureate complexes of zirconium — Probing the role of the tether in ligand design
  作者：Philippa R. Payne、Jason A. Bexrud、David C. Leitch、Laurel L. Schafer

  DOI：10.1139/v11-091

  日期：2011.10

  Simple chiral proligands have been synthesized from inexpensive chiral starting materials. These amidate and ureate ligands support zirconium complexes that successfully catalyze intramolecular hydroamination with up to 26% ee. Several elements necessary for successful ligand design are highlighted and discussed. In particular, the strict control of metal geometry through multidentate tethered ligands is determined to be an essential aspect of future ligand development.

  简单手性前体已经从廉价的手性起始物质合成。这些酰胺和脲配体支持锆配合物，成功催化了高达26%的内分子氢胺化反应。强调和讨论了成功配体设计所需的几个要素。特别是，通过多齿联结配体严格控制金属几何构型被确定为未来配体开发的一个关键方面。