(S)-2-(1-adamantyl)-2-aminoethanol | 328969-78-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(1-adamantyl)-2-aminoethanol
• 英文别名: (R)-2-adamantyl-2-aminoetanol；(R)-2-(Adamantan-1-yl)-2-aminoethanol；(2R)-2-(1-adamantyl)-2-aminoethanol
• CAS: 328969-78-4
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: HBUUJKSRVMGCEK-CRCJWISWSA-N

物化性质

• 沸点：
  338.9±15.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲基丙二酰二氯 、 (S)-2-(1-adamantyl)-2-aminoethanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到N,N'-bis[(1R)-(1-adamantyl)-2-hydroxyethyl]-2,2-dimethyl-1,3-propanodiamide
  参考文献：
  名称：

  2,2′-Isopropylidenebis[(4R)-(1-adamantyl)-2-oxazoline] (Adam-Box). A new enantiopure C2-symmetrical ligand: enantioselective cyclopropanations, Diels–Alder reactions, and allylic oxidations

  摘要：

  The title bisoxazoline (Box) featuring two adamantane skeletons (Adam-Box) is a ligand of (R,R)-configuration, which combined with copper sources makes excellent catalysts for enantioselective cyclopropanations, Diels-Alder reactions, and allylic oxidations. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00404-4
• 作为产物：
  描述：

  (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (S)-2-(1-adamantyl)-2-aminoethanol
  参考文献：
  名称：

  Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

  摘要：

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00428-6

文献信息

• Stereoselective Alkylation of Chiral Titanium(IV) Enolates with <i>tert</i>-Butyl Peresters
  作者：Marina Pérez-Palau、Nil Sanosa、Pedro Romea、Fèlix Urpí、Rosa López、Enrique Gómez-Bengoa、Mercè Font-Bardia

  DOI：10.1021/acs.orglett.1c03366

  日期：2021.11.19

  Here, we present a new stereoselective alkylation of titanium(IV) enolates of chiral N-acyl oxazolidinones with tert-butyl peresters from Cα-branched aliphatic carboxylic acids, which proceeds through the decarboxylation of the peresters and the subsequent formation of alkyl radicals to produce the alkylated adducts with an excellent diastereoselectivity. Theoretical calculations account for the observed

  在这里，我们提出了一种新的立体选择性烷基化手性N-酰基恶唑烷酮的钛 (IV) 烯醇化物与来自 Cα-支链脂肪族羧酸的叔丁基过酸酯，该反应通过过酸酯的脱羧和随后形成的烷基自由基进行烷基化加合物具有优异的非对映选择性。理论计算解释了观察到的反应性和出色的立体控制。重要的是，所得化合物可以很容易地转化为不对称和催化转化的配体。
• Highly Enantioselective Electrophilic Amination and Michael Addition of Cyclic β-Ketoesters Induced by Lanthanides and (<i>S</i>,<i>S</i>)-ip-pybox:  The Mechanism
  作者：Josep Comelles、Àlex Pericas、Marcial Moreno-Mañas、Adelina Vallribera、Galí Drudis-Solé、Agusti Lledos、Teodor Parella、Anna Roglans、Santiago García-Granda、Laura Roces-Fernández

  DOI：10.1021/jo0622678

  日期：2007.3.1

  High enantioselection is obtained in Michael additions of cyclic beta-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and beta-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.
• 2,2′-Isopropylidenebis[(4R)-(1-adamantyl)-2-oxazoline] (Adam-Box). A new enantiopure C2-symmetrical ligand: enantioselective cyclopropanations, Diels–Alder reactions, and allylic oxidations
  作者：Jaume Clariana、Josep Comelles、Marcial Moreno-Mañas、Adelina Vallribera

  DOI：10.1016/s0957-4166(02)00404-4

  日期：2002.8

  The title bisoxazoline (Box) featuring two adamantane skeletons (Adam-Box) is a ligand of (R,R)-configuration, which combined with copper sources makes excellent catalysts for enantioselective cyclopropanations, Diels-Alder reactions, and allylic oxidations. (C) 2002 Published by Elsevier Science Ltd.
• Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: a combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution
  作者：Jaume Clariana、Santiago Garcı́a-Granda、Vicente Gotor、Angel Gutiérrez-Fernández、Amparo Luna、Marcial Moreno-Mañas*、Adelina Vallribera

  DOI：10.1016/s0957-4166(00)00428-6

  日期：2000.11

  Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1. (C) 2000 Elsevier Science Ltd. All rights reserved.