(S)-3-Methyl-2-((S)-2-methyl-1-pyridin-2-yl-propylamino)-butan-1-ol | 192223-60-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-3-Methyl-2-((S)-2-methyl-1-pyridin-2-yl-propylamino)-butan-1-ol
• 英文别名: (2S)-3-methyl-2-[[(1S)-2-methyl-1-pyridin-2-ylpropyl]amino]butan-1-ol
• CAS: 192223-60-2
• 化学式: C₁₄H₂₄N₂O
• 分子量: 236.357
• InChiKey: DMXNMRQRKFDFHG-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-Methyl-2-((S)-2-methyl-1-pyridin-2-yl-propylamino)-butan-1-ol 在 高碘酸 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (1S)-2-甲基-1-(2-吡啶基)-1-丙胺
  参考文献：
  名称：

  Addition of Organozincate Reagents to Imines Derived from (S)-1-Phenylethylamine and Ethyl (S)-Valinate—Synthesis of (S)-1-(2-Pyridyl)Alkylamines

  摘要：

  AbstractTriorganozincates were added to aliphatic aldimines derived from (S)‐1‐phenylethylamine and (S‐valine esters in the presence of boron trifluoride to give secondary amines with low diastereoselectivies. From mixed zincates, most alkyl groups (methyl, ethyl, 1‐heptynyl, but not tert‐butyl) could be transferred. No addition to benzaldimines was observed, but the imines prepared from 2‐pyridinecarboxaldehyde did not require activation by BF3 and underwent selective group transfer from mixed zincates at — 78°C. Excellent diastereoselectivities were observed in the reactions of the 2‐pyridine imine derived from ethyl (S)‐valinate with mixed zincates, in which the methyl group was used as nontransferable ligand, allowing the transfer of alkyl and vinyl groups with excellent to complete selectivity. However, dimethyl(aryl)‐ and dimethyl‐(1‐heptynyl)zincates did not react. (S)‐1‐(2‐Pyridyl)alkylamines were prepared with high optical purity by subsequent removal of the chiral auxiliary.

  DOI：

  10.1002/chem.19970030512
• 作为产物：
  描述：

  (S,E)-3-methyl-2-(pyridin-2-ylmethyleneamino)butan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-3-Methyl-2-((S)-2-methyl-1-pyridin-2-yl-propylamino)-butan-1-ol
  参考文献：
  名称：

  Alvaro, Giuseppe; Martelli, Gianluca; Savoia, Diego, Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 775 - 783

  摘要：

  DOI：

文献信息

• The Reaction of β-Amino Alcohols with 1,1′-Carbonyldiimidazole − Influence of the Nitrogen Substituent on the Reaction Course
  作者：Sara Cutugno、Gianluca Martelli、Lucia Negro、Diego Savoia

  DOI：10.1002/1099-0690(200102)2001:3<517::aid-ejoc517>3.0.co;2-n

  日期：2001.2

  The reaction of β-amino alcohols with 1,1′-carbonyldiimidazole in dichloromethane is affected by the size of the nitrogen substituent. 1,3-Oxazolidin-2-ones are exclusively obtained from N-H, N-methyl and N-arylmethyl derivatives. O-(1-Imidazolyl)carbonyl derivatives are formed as intermediates from N-[1-(2-pyridyl)alkyl]-(S)-valinol and are mainly or exclusively converted into aziridines in the presence

  β-氨基醇与 1,1'-羰基二咪唑在二氯甲烷中的反应受氮取代基大小的影响。1,3-Oxazolidin-2-ones 仅从 NH、N-甲基和 N-芳甲基衍生物中获得。O-(1-咪唑基)羰基衍生物作为中间体由 N-[1-(2-吡啶基)烷基]-(S)-缬氨醇形成，主要或仅在水存在下转化为氮丙啶，尽管环化是被三苯甲基等大的 N 取代基阻碍。
• Design and synthesis of enantiopure 1-[1( S )-(2-pyridyl)alkyl]-2( R )-isopropylaziridines, new ligands for asymmetric catalysis
  作者：Katia Fiore、Gianluca Martelli、Magda Monari、Diego Savoia

  DOI：10.1016/s0957-4166(99)00571-6

  日期：1999.12

  Enantiopure 1-(2-pyridyl)alkyl aziridines were designed as bidentate ligands for asymmetric catalysis. Their synthesis involved the addition of organometallic reagents to the imine prepared from 2-pyridinealdehyde and an enantiopure β-aminoalcohol, followed by cyclisation of the β-aminoalcohol moiety to the aziridine ring. Two such ligands (N–N)* were prepared from (S)-valinol and converted to the

  对映体纯1-（2-吡啶基）烷基氮丙啶被设计为用于不对称催化的双齿配体。他们的合成涉及将有机金属试剂添加到由2-吡啶醛和对映体纯的β-氨基醇制得的亚胺中，然后将β-氨基醇部分环化到氮丙啶环上。两个这样的配体（N-N）*购自（制备小号） -缬氨醇并转化为复合物（η 3 -烯丙基）（N-N）*的Pd +的SbF 6 - ，其中一个用X射线晶体学。在代表性的Pd催化的烯丙基取代反应中实现适度的对映选择性。
• Alvaro, Giuseppe; Martelli, Gianluca; Savoia, Diego, Journal of the Chemical Society. Perkin transactions I, 1998, # 4, p. 775 - 783
  作者：Alvaro, Giuseppe、Martelli, Gianluca、Savoia, Diego

  DOI：——

  日期：——
• Addition of Organozincate Reagents to Imines Derived from (S)-1-Phenylethylamine and Ethyl (S)-Valinate—Synthesis of (S)-1-(2-Pyridyl)Alkylamines
  作者：Giuseppe Alvaro、Paolo Pacioni、Diego Savoia

  DOI：10.1002/chem.19970030512

  日期：1997.5

  AbstractTriorganozincates were added to aliphatic aldimines derived from (S)‐1‐phenylethylamine and (S‐valine esters in the presence of boron trifluoride to give secondary amines with low diastereoselectivies. From mixed zincates, most alkyl groups (methyl, ethyl, 1‐heptynyl, but not tert‐butyl) could be transferred. No addition to benzaldimines was observed, but the imines prepared from 2‐pyridinecarboxaldehyde did not require activation by BF3 and underwent selective group transfer from mixed zincates at — 78°C. Excellent diastereoselectivities were observed in the reactions of the 2‐pyridine imine derived from ethyl (S)‐valinate with mixed zincates, in which the methyl group was used as nontransferable ligand, allowing the transfer of alkyl and vinyl groups with excellent to complete selectivity. However, dimethyl(aryl)‐ and dimethyl‐(1‐heptynyl)zincates did not react. (S)‐1‐(2‐Pyridyl)alkylamines were prepared with high optical purity by subsequent removal of the chiral auxiliary.