(2R)-2-(dibenzylamino)-3-methylbutan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-(dibenzylamino)-3-methylbutan-1-ol
• 英文别名: (R)-2-(dibenzylamino)-3-methylbutan-1-ol；(R)-2-(Dibenzylamino)-3-methyl-1-butanol
• 化学式: C₁₉H₂₅NO
• 分子量: 283.414
• InChiKey: ZWLAXLXECFRUPM-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-(dibenzylamino)-3-methylbutan-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 5.08h， 生成
  参考文献：
  名称：

  SYNTHESIS OF THERAPEUTIC AND DIAGNOSTIC DRUGS CENTERED ON REGIOSELECTIVE AND STEREOSELECTIVE RING OPENING OF AZIRIDINIUM IONS

  摘要：

  通过氮杂环丙烷离子的亲核环开反应，立体选择性和区域选择性合成化合物，用于立体选择性和区域选择性合成治疗和诊断化合物。

  公开号：

  US20130310555A1
• 作为产物：
  描述：

  D-缬氨酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 14.5h， 生成 (2R)-2-(dibenzylamino)-3-methylbutan-1-ol
  参考文献：
  名称：

  Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds

  摘要：

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.079

文献信息

• Easily Accessible ChiralP,N-Bidentate Aryl Phosphites, Their Complexation and Application in Enantioselective Allylic Alkylation, Sulfonylation and Hydrosilylation
  作者：Konstantin N. Gavrilov、Oleg G. Bondarev、Roman V. Lebedev、Alexei A. Shiryaev、Sergey E. Lyubimov、Alexei I. Polosukhin、Gennady V. Grintselev-Knyazev、Konstantin A. Lyssenko、Sergey K. Moiseev、Nikolay S. Ikonnikov、Valery N. Kalinin、Vladim A. Davankov、Andrei V. Korostylev、Hans-Joachim Gais

  DOI：10.1002/1099-0682(200206)2002:6<1367::aid-ejic1367>3.0.co;2-f

  日期：2002.6

  [Rh(CO)Cl(η2-P∩N)], [PdCl2(η2-P∩N)] and [Pd(allyl)(η2-P∩N)]+Cl−, respectively. With these new P,N-ligands, up to 82% ee enantioselectivity was achieved in the Pd-catalysed alkylation of ethyl 3-penten-2-yl carbonate with dimethyl malonate, up to 80% ee in the Pd-catalysed sulfonylation of methyl 3-penten-2-yl carbonate with sodium p-toluenesulfinate, and up to 50% ee in the Rh-catalysed hydrosilylation

  通过氨基和亚氨基醇的一步磷酸化获得了新的手性 P,N-杂化芳基亚磷酸酯。发现新配体与 [Rh(CO)2Cl]2、[Pd(COD)Cl2] 和 [Pd(烯丙基)Cl]2 的络合得到螯合物 [Rh(CO)Cl(η2-P∩N) ]、[PdCl2(η2-P∩N)] 和 [Pd(allyl)(η2-P∩N)]+Cl− 分别。使用这些新的 P,N-配体，在 Pd 催化的 3-戊烯-2-基碳酸乙酯与丙二酸二甲酯的烷基化中实现了高达 82% 的 ee 对映选择性，在 Pd 催化的甲基磺酰化中实现了高达 80% ee 的对映选择性3-戊烯-2-基碳酸酯与对甲苯亚磺酸钠，以及在 Rh 催化的苯乙酮与二苯基硅烷的氢化硅烷化中高达 50% 的 ee。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• New amino-, imino- and oxazolinophosphites based on 1,1′-bi-2-naphtol: coordination and catalytic properties
  作者：K.N Gavrilov、O.G Bondarev、R.V Lebedev、A.I Polosukhin、A.A Shyryaev、S.E Lyubimov、P.V Petrovskii、S.K Moiseev、V.N Kalinin、N.S Ikonnikov、V.A Davankov、A.V Korostylev

  DOI：10.1016/s0022-328x(02)01561-9

  日期：2002.8

  A series of the new chiral BINOL-based phosphite P,N-hybrid ligands was prepared. The coordination behavior of all the ligands was studied and the neutral complexes [Rh(CO)Cl(P<^>N)] were synthesized in order to characterize a degree of the electronic non-symmetry of donating centers. Also the neutral and cationic complexes cis-[PdCl2(eta(2)-P<^>N=)], cis-[PdCl2(eta(1)-P<^>N=)(2)], cis-[PdCl(eta(2)-P<^>N=)(eta(1)-P<^>N=)]Cl-+(-), [Pd(allyl)(eta(2)-P<^>N=)]X-+(-) (X- = Cl-, BF4-) were obtained and characterized. The new P,N-hydrid ligands gave up to 81% ee in the enantioselective Pd-catalyzed alkylation of 3-penten-2-yl carbonate by dimethyl malonate and up to 60% ee in the Rh-catalyzed hydrosilylation of acetophenone and acetylferrocene by diphenylsilane. (C) 2002 Elsevier Science B.V. All rights reserved.
• SYNTHESIS OF THERAPEUTIC AND DIAGNOSTIC DRUGS CENTERED ON REGIOSELECTIVE AND STEREOSELECTIVE RING OPENING OF AZIRIDINIUM IONS
  申请人：Chong Hyun-Soon

  公开号：US20130310555A1

  公开（公告）日：2013-11-21

  Stereoselective and regioselective synthesis of compounds via nucleophilic ring opening reactions of aziridinium ions for use in stereoselective and regioselective synthesis of therapeutic and diagnostic compounds.

  通过氮杂环丙烷离子的亲核环开反应，立体选择性和区域选择性合成化合物，用于立体选择性和区域选择性合成治疗和诊断化合物。
• Synthesis of 15N-labeled vicinal diamines through N-activated chiral aziridines: tools for the NMR study of platinum-based anticancer compounds
  作者：Gilles Berger、Michel Gelbcke、Emilie Cauët、Michel Luhmer、Jean Nève、François Dufrasne

  DOI：10.1016/j.tetlet.2012.11.079

  日期：2013.2

  A new method for the synthesis of N-15-labeled chiral beta-diamines from a common precursor, either optically pure amino acids or anti-beta-amino alcohols, is reported. The two diastereomeric series of vicinal diamines are produced through the nucleophilic ring opening of activated chiral aziridines. N-15 was introduced by means of [N-15]-benzylamine, prepared from (NH4Cl)-N-15. The final compounds are highly valuable because [H-1-N-15] NMR is considered a powerful tool for studying the chemical properties of platinum-based complexes. (C) 2012 Elsevier Ltd. All rights reserved.