(2R,4R)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]pentane-2,4-diamine | 1172598-41-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,4R)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]pentane-2,4-diamine
• CAS: 1172598-41-2
• 化学式: C₁₇H₄₂N₂O₂Si₂
• 分子量: 362.704
• InChiKey: MESFYWLNGNIOAV-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]pentane-2,4-diamine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到(2R,4R)-2,4-diaminopentane-1,5-diol dihydrochloride
  参考文献：
  名称：

  从新型戊醇衍生的双-β-氨基醇合成新的 4,4'-双（恶唑啉）AraBOX

  摘要：

  描述了新型苯基 ​​4,4'-双(恶唑啉) [AraBOX] 的制备。新型配体由双-[(O-甲硅烷基)β-氨基醇]通过两个有效步骤制备，通过转化为中间体双（苯甲酰胺），然后是一锅脱保护-活化-闭环（DARC）恶唑啉形成。据我们所知，这是首次报道通过这种 DARC 方法合成恶唑啉环。还描述了两种前体双-β-氨基醇的合成，(2R,4R)-和 meso-2,4-diaminopentane-1,5-diol，分别衍生自 D-(+)-arabitol 和木糖醇.

  DOI：

  10.1055/s-0029-1216731
• 作为产物：
  描述：

  [(2S,4S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-methylsulfonyloxypentan-2-yl] methanesulfonate 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 85.0 ℃ 、500.01 kPa 条件下， 反应 112.0h， 以76%的产率得到(2R,4R)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]pentane-2,4-diamine
  参考文献：
  名称：

  从新型戊醇衍生的双-β-氨基醇合成新的 4,4'-双（恶唑啉）AraBOX

  摘要：

  描述了新型苯基 ​​4,4'-双(恶唑啉) [AraBOX] 的制备。新型配体由双-[(O-甲硅烷基)β-氨基醇]通过两个有效步骤制备，通过转化为中间体双（苯甲酰胺），然后是一锅脱保护-活化-闭环（DARC）恶唑啉形成。据我们所知，这是首次报道通过这种 DARC 方法合成恶唑啉环。还描述了两种前体双-β-氨基醇的合成，(2R,4R)-和 meso-2,4-diaminopentane-1,5-diol，分别衍生自 D-(+)-arabitol 和木糖醇.

  DOI：

  10.1055/s-0029-1216731

文献信息

• AraBOX and XyliBOX based catalysts for cyclopropanations, Diels Alder cycloadditions and allylic additions
  作者：David Kellehan、Fiona Kirby、David Frain、Antonio M. Rodríguez-García、José I. García、Patrick O’Leary

  DOI：10.1016/j.tetasy.2013.04.020

  日期：2013.6

  The syntheses of three novel chiral 4,4'BOX ligands are described. The three ligands each have a chiral backbone and chiral sidearms, two of which are diastereomeric. These new ligands have been applied as copper complexes to asymmetric cyclopropanation reaction of styrene with ethyldiazoacetate. Enantioselectivities of up to 70% were obtained, which is the highest ee reported from the use of this ligand class in this reaction to date. The multiple stereogenic centres in the ligand resulted in a substantial additive effect and this is discussed along with interpretation of the results for previously described 4,4'BOX ligands, and a major computational study of the multiple reaction channels involved with ligands of this type. The use of complexes of 4,4'BOX ligands, as catalysts, in an allylic alkylation is also reported for the first time and ee's of >70% have been achieved in this reaction. These ligands were also applied to a Diels-Alder test reaction and again outperformed previous examples of this ligand type. (C) 2013 Elsevier Ltd. All rights reserved.
• Preparation, structure and catalytic activity of copper(II) complexes of novel 4,4′-BOX ligands
  作者：David Frain、Fiona Kirby、Patrick McArdle、Patrick O’Leary

  DOI：10.1016/j.tetlet.2010.05.135

  日期：2010.8

  This Letter details the synthesis of two new 4,4'-bisoxazoline (BOX) ligands. The copper(II) complex of one of the new ligands is structurally determined. The catalytic performance of the copper(II) complexes of the novel ligands, and that of our recently described phenyl AraBOX ligand in Diels-Alder reactions are reported. We have used the structural information to propose an explanation of a curious variation in the diastereoselectivity obtained in the case of one ligand complex. (C) 2010 Elsevier Ltd. All rights reserved.
• The Synthesis of AraBOX, a New 4,4′-Bis(oxazoline), from Novel Pentitol-Derived Bis-β-amino Alcohols
  作者：Patrick O’Leary、David Frain、Fiona Kirby、Patrick McArdle

  DOI：10.1055/s-0029-1216731

  日期：——

  phenyl 4,4'-bis(oxazoline) [AraBOX] is described. The novel ligand is prepared in two efficient steps from a bis-[(O-silyl)β-amino alcohol], via conversion into an intermediate bis(benzamide) followed by a one-pot deprotection-activation-ring closure (DARC) oxazoline formation. To our knowledge, this is the first reported synthesis of an oxazoline ring via this DARC method. The synthesis of two precursor

  描述了新型苯基 ​​4,4'-双(恶唑啉) [AraBOX] 的制备。新型配体由双-[(O-甲硅烷基)β-氨基醇]通过两个有效步骤制备，通过转化为中间体双（苯甲酰胺），然后是一锅脱保护-活化-闭环（DARC）恶唑啉形成。据我们所知，这是首次报道通过这种 DARC 方法合成恶唑啉环。还描述了两种前体双-β-氨基醇的合成，(2R,4R)-和 meso-2,4-diaminopentane-1,5-diol，分别衍生自 D-(+)-arabitol 和木糖醇.