tris<(S)-2-aminopropyl>amine | 137460-55-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tris<(S)-2-aminopropyl>amine
• 英文别名: tris[(S)-2-aminopropyl]amine；(2S)-1-N,1-N-bis[(2S)-2-aminopropyl]propane-1,2-diamine
• CAS: 137460-55-0
• 化学式: C₉H₂₄N₄
• 分子量: 188.316
• InChiKey: WUEHOBBABKCBHF-CIUDSAMLSA-N

物化性质

• 沸点：
  248.2±8.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tris<(S)-2-aminopropyl>amine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 72.08h， 生成
  参考文献：
  名称：

  显示对映选择性阴离子结合的预组织同手性吡咯受体

  摘要：

  在此，提出了一系列用于阴离子识别的三(吡咯酰胺)受体。这些受体能够以良好的亲和力与多种阴离子结合，并且纯手性受体对 ( S )-(+)-扁桃酸的亲和力是 ( R )-(−)-扁桃酸的 1.6 倍，这表明其能够区分这些对映体阴离子。

  DOI：

  10.1002/ejoc.202101346
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 生成 tris<(S)-2-aminopropyl>amine
  参考文献：
  名称：

  Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers

  摘要：

  Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host-guest recognition or as supramolecular catalysts. The unprecedented control of the helical chirality of the CTV unit by remote stereogenic centers of a tren moiety is reported, providing an original access to this highly promising class of host molecules. Although the chiral centers and the CTV unit are separated by more than 10 angstrom, one single diastereomer is formed; the nature of the diastereoselective process is discussed and the procedure is exemplified using different enantiopure tren derivatives. This work also highlights the influence of the chirality of the CTV unit on the whole cage structure.

  DOI：

  10.1021/ol5035194

文献信息

• A General Method for the Preparation of Chiral TREN Derivatives
  作者：Yuxin Pei、Katja Brade、Emilie Brulé、Lars Hagberg、Fredrik Lake,、Christina Moberg

  DOI：10.1002/ejoc.200500094

  日期：2005.7

  A general procedure for the preparation of C-3-symmetric TREN derivatives with backbone chirality has been developed. Stereo- and regioselective ring opening by ammonia of (S)-N-tosyl-2-isopropylaziridine, obtained starting from either the corresponding amino alcohol or amino acid, followed by deprotection of the amino groups afforded the parent chiral TREN compound in high overall yield. In addition

  已开发出制备具有主链手性的 C-3 对称 TREN 衍生物的一般程序。从相应的氨基醇或氨基酸开始，通过氨对 (S)-N-tosyl-2-isopropylaziridine 进行立体和区域选择性开环，然后对氨基进行脱保护，以高总产率提供母体手性 TREN 化合物. 除了具有伯氨基的 TREN 化合物外，所采用的合成方法还可以轻松获得各种 N,N',N-取代衍生物。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)。
• Heterochiral Diastereomer-Discriminative Diphanes That Form Hierarchical Superstructures with Nonlinear Optical Properties
  作者：Jiaolong Chen、Zhenyu Yang、Gucheng Zhu、Enguang Fu、Pan Li、Fangyi Chen、Chunyang Yu、Shiyong Wang、Shaodong Zhang

  DOI：10.1021/jacsau.2c00225

  日期：2022.7.25

  homochirality during complex molecular systems, most works mainly concentrated on the resolution of a pair of enantiomers. However, the preference of homochiral over heterochiral isomers has been overlooked, with very limited examples focusing only on noncovalent interactions. We herein report on diastereomeric discrimination of twin-cavity cages (denoted as diphanes) against heterochiral tris-(2-aminopropyl)amine

  为了研究复杂分子系统中同手性的出现，大多数工作主要集中在一对对映异构体的拆分上。然而，纯手性对异手性异构体的偏好被忽视了，仅关注非共价相互作用的例子非常有限。我们在此报告了双腔笼（表示为联苯）对带有三重立体中心的异手性三-（2-氨基丙基）胺（TRPN）的非对映异构体歧视。这种非对映体选择性源于 TRPN 上反应性仲胺的不同空间取向。所有反应性部分以相同方式旋转的纯手性TRPN促进纯手性和非手性内消旋二烷的形成具有低应变能，而具有不均匀仲胺取向的异手性TRPN阻止了笼状实体的形成，因为虚拟二烷表现出相当高的应变。此外，纯手性二烷自组装成由单手螺旋组成的无心超结构，表现出有趣的非线性光学行为。这种特性对于有机笼来说是一种独特的现象，因此展示了它们产生具有有趣特性和功能的新型材料的潜力。
• Synthesis, stereochemical characterisation and absolute configuration of enantiomerically pure complexes of sexidentate ligands
  作者：Peter Kremminger、Walter Weissensteiner

  DOI：10.1007/bf00809812

  日期：——

  The optically active sexidentate Schiff bases [H3L5] and [H3L6] were prepared from tris[(S)-2-aminopropyl]amine and 5-chlor- and 5-isopropylsalicylaldehyde, respectively. Reaction of rhodium trichloride with [H3L6] gave an enantiomerically pure [RhL6] complex with an absolute configuration of LAMBDA-for the octahedral arrangement. The chiroptical properties are given.
• Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers
  作者：Bastien Chatelet、Lionel Joucla、Daniele Padula、Lorenzo Di Bari、Guillaume Pilet、Vincent Robert、Véronique Dufaud、Jean-Pierre Dutasta、Alexandre Martinez

  DOI：10.1021/ol5035194

  日期：2015.2.6

  Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host-guest recognition or as supramolecular catalysts. The unprecedented control of the helical chirality of the CTV unit by remote stereogenic centers of a tren moiety is reported, providing an original access to this highly promising class of host molecules. Although the chiral centers and the CTV unit are separated by more than 10 angstrom, one single diastereomer is formed; the nature of the diastereoselective process is discussed and the procedure is exemplified using different enantiopure tren derivatives. This work also highlights the influence of the chirality of the CTV unit on the whole cage structure.
• Preorganized Homochiral Pyrrole‐Based Receptors that Display Enantioselective Anion Binding
  作者：Johannes Karges、Seth M. Cohen

  DOI：10.1002/ejoc.202101346

  日期：2022.4.27

  Herein, a series of tris(pyrrolamide) receptors for anion recognition is presented. The receptors were able to bind to a variety of anions with good affinity, and homochiral receptors produced a 1.6-fold greater affinity for (S)-(+)-mandelate over (R)-(−)-mandelate, demonstrating the ability to differentiate between these enantiomeric anions.

  在此，提出了一系列用于阴离子识别的三(吡咯酰胺)受体。这些受体能够以良好的亲和力与多种阴离子结合，并且纯手性受体对 ( S )-(+)-扁桃酸的亲和力是 ( R )-(−)-扁桃酸的 1.6 倍，这表明其能够区分这些对映体阴离子。