(2S)-N¹,N¹-bis[(S)-2-amino-3-methylbutyl]-3-methylbutane-1,2-diamine | 857722-05-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-N¹,N¹-bis[(S)-2-amino-3-methylbutyl]-3-methylbutane-1,2-diamine
• 英文别名: (2S)-1-N,1-N-bis[(2S)-2-amino-3-methylbutyl]-3-methylbutane-1,2-diamine
• CAS: 857722-05-5
• 化学式: C₁₅H₃₆N₄
• 分子量: 272.478
• InChiKey: VGPQMGDISDYTSC-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  9
• 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：

  (2S)-N¹,N¹-bis[(S)-2-amino-3-methylbutyl]-3-methylbutane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (S,S,S)-tris[2-(2'-diphenylphosphinobenzamino)-3-methylbutyl]amine
  参考文献：
  名称：

  模块化多齿膦配体：应用于钯催化的烯丙基烷基化反应。

  摘要：

  通过使（S）-N-甲苯磺酰基-2-异丙基氮丙啶与氨，伯胺和仲胺的开环反应，与非手性含磷结构单元反应，制备手性多齿胺，可轻松获得多齿膦。该膦用于钯催化的rac-3-环己烯基碳酸酯和环戊烯基碳酸酯的烷基化。对映选择性和反应性主要取决于配体胺核的结构。与六元底物的反应中观察到高达88％ee。

  DOI：

  10.1039/b513906f
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 生成 (2S)-N¹,N¹-bis[(S)-2-amino-3-methylbutyl]-3-methylbutane-1,2-diamine
  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)。
• Protonation of Tris(iminocatecholato) Complexes of Gallium(III) and Titanium(IV)
  作者：Markus Albrecht、Simon Burk、Ralf Stoffel、Arne Lüchow、Roland Fröhlich、Michael Kogej、Christoph A. Schalley

  DOI：10.1002/ejic.200601206

  日期：2007.4

  The coordination behaviour of the chiral tren-type tripodal ligand 3-H6 with gallium(III) and titanium(IV) ions was investigated and it was found that only mononuclear complexes are formed. In the presence of Na+, one of the cations acts as a template and is bound inside the “cap” of [Na(3)M]n– (M = Ga, n = 2; M = Ti, n = 1). If no such cation is present, three protons are bound to the iminocatechol

  研究了手性 tren 型三足配体 3-H6 与镓 (III) 和钛 (IV) 离子的配位行为，发现仅形成单核配合物。在存在 Na+ 的情况下，其中一个阳离子充当模板并结合在 [Na(3)M]n–（M = Ga，n = 2；M = Ti，n = 1）的“帽”内。如果不存在这样的阳离子，则三个质子与亚氨基儿茶酚单元结合，以防止氮和氧孤对之间的排斥。为了最小化 [H3(3)M]n+ (M = Ga, n = 0; M = Ti, n = 1) 的质子化亚胺之间的电荷排斥，烯胺酮 / chinomethine 中间体结构变得重要。计算方法支持亚氨基儿茶酚酸盐采用这种不寻常的中间体形式。在进一步的调查中，我们发现，将质子 (H2SO4) 添加到双核（儿茶酚亚胺）钛螺旋 K4[(4)3Ti2] 会导致亚氨基儿茶酚的亚胺部分质子化。过量的酸导致配合物以及亚胺单元的水解。(© Wiley-VCH Verlag
• Synthesis and VCD Spectroscopic Characterization of a Series of Azacryptands from a Chiral Valine‐Based Derivative of Tris(2‐aminoethyl)amine (TREN)
  作者：Clemens Müller、Kevin Scholten、Elric Engelage、Christian Merten

  DOI：10.1002/chem.202302126

  日期：2023.11.13

  We introduce three C3-symmetric azacryptands with chiral valine-based TREN headgroups. Their VCD spectroscopic characterization reveals that the computed lowest energy conformers of all three azacryptands are not favored in solution phase and that they prefer a collapsed conformation.

  我们引入了三种具有基于手性缬氨酸的TREN头基的C 3对称氮杂密码配体。他们的 VCD 光谱表征表明，计算出的所有三种氮杂密码配体的最低能量构象异构体在溶液相中均不受欢迎，并且它们更喜欢塌陷构象。
• Chelating phosphines with C2 and C3 symmetry
  作者：Emilie Brulé、Yuxin Pei、Fredrik Lake、Fredrik Rahm、Christina Moberg

  DOI：10.1070/mc2004v014n06abeh002026

  日期：2004.1

  Antide formation between ring opened aziridines and 2-(diphenylphosphino)benzoic acid provides an easy access to chelating di- and triphosphines with C-2 and C-3 symmetry.
• Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations
  作者：Yuxin Pei、Emilie Brulé、Christina Moberg

  DOI：10.1039/b513906f

  日期：——

  Multidentate phosphines were readily obtained by reaction of chiral multidentate amines, prepared via ring opening of (S)-N-tosyl-2-isopropylaziridine with ammonia, primary, and secondary amines, with achiral phosphorus containing building blocks. The phosphines were used in palladium-catalyzed alkylation of rac-3-cyclohexenyl and cyclopentenyl carbonates. The enantioselectivity and reactivity were

  通过使（S）-N-甲苯磺酰基-2-异丙基氮丙啶与氨，伯胺和仲胺的开环反应，与非手性含磷结构单元反应，制备手性多齿胺，可轻松获得多齿膦。该膦用于钯催化的rac-3-环己烯基碳酸酯和环戊烯基碳酸酯的烷基化。对映选择性和反应性主要取决于配体胺核的结构。与六元底物的反应中观察到高达88％ee。