(S)-N¹,N²-di-i-butoxycarbonyl-1,2,4,-triaminobutane | 148357-94-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N¹,N²-di-i-butoxycarbonyl-1,2,4,-triaminobutane
• 英文别名: (S)-N¹,N²-di-i-butoxycarbonyl-1,2,4-triaminobutane；(S)-diisobutyl(4-aminobutane-1,2-diyl)dicarbamate；2-methylpropyl N-[(2S)-4-amino-1-(2-methylpropoxycarbonylamino)butan-2-yl]carbamate
• CAS: 148357-94-2
• 化学式: C₁₄H₂₉N₃O₄
• 分子量: 303.402
• InChiKey: QDCKHXPPCJLXNO-LBPRGKRZSA-N

物化性质

• 沸点：
  457.1±40.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N¹,N²-di-i-butoxycarbonyl-1,2,4,-triaminobutane 在 盐酸 作用下， 反应 10.0h， 以83%的产率得到(S)-1,2,4-triaminobutane trihydrochloride
  参考文献：
  名称：

  Synthesis of chiral 1,2,4-triaminobutanes

  摘要：

  (S)-5-(Azidomethyl)-2-pyrrolidone, obtained by the Mitsunobu reaction, was reduced to (S)-5-(aminomethyl)-2-pyrrolidone which was hydrolysed to (S)-4,5-diaminovaleric acid. The acid, after acylation with i-butyl or with (1R, 3R, 4S)-menthyl chloroformate, underwent a Curtius reaction yielding the corresponding (S)-1,2-dialkoxycarbonyl-1,2,4-triaminobutane. Alternatively, (S)-5-(aminomethyl)-2-pyrrolidone was subjected to exhaustive t-butoxycarbonylation followed by ring-cleavage with ammonia to give (S)-N4,N5,N5-triboc-4,5-diaminovaleramide and was converted by a Hofmann rearrangement to (S)-N1,N2-di-t-butoxy carbonyl-4-methoxycarbonyl-1,2,4-triaminobutane.

  DOI：

  10.1016/s0957-4166(00)86019-x
• 作为产物：
  描述：

  (S)-N⁴,N⁵-di-i-butoxycarbonyl-4,5-diaminovaleric acid 在 N-甲基吗啉 、 碘苯二乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 21.5h， 生成 (S)-N¹,N²-di-i-butoxycarbonyl-1,2,4,-triaminobutane
  参考文献：
  名称：

  Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis

  摘要：

  The title compounds H2NCH((CH2)(n)NMe2)CH2NH2 L1-1A (n = 1-4) are efficiently synthesized in enantiopure form. The commercial starting materials, L-asparagine, (S)-5-hydroxymethy1-2-pyrrolidinone, and (S)-6-(((benzyloxy)carbonyI)-amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid, are elaborated in 6-9 standard steps to giye Ll (18% overall), 12 (13%), L3 (36%) and LA (38%) or the corresponding tris(hydrochloric acid) salts [H3NCH((CH2)(n)NHMe2)CH2NH3](3+) 3Cl(-), which are preferable for long term storage. The sequences make use of isobutyl carbamate, Cbz, and Boc protecting groups and Hofmann type rearrangements; the dimethylamino groups are introduced at late stages, either via reductive dimethylations or nucleophilic displacements involving mesylates and HNMe2. L1-L4 chelate to [Co(en)(2)](3+) fragments to give octahedral complexes that catalyze numerous enantioselective reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.012

文献信息

• [EN] TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS<br/>[FR] COMPLEXES DE MÉTAL DE TRANSITION POUR LA CATALYSE ÉNANTIOSÉLECTIVE DE RÉACTIONS DE FORMATION DE LIAISONS CARBONE-CARBONE, CARBONE-HÉTÉROATOME ET CARBONE-HYDROGÈNE
  申请人：TEXAS A & M UNIV SYS

  公开号：WO2014018978A3

  公开（公告）日：2014-04-10