(S)-2-((R)-azido(phenyl)methyl)-1-benzylpyrrolidine | 1448991-14-7

• 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: (S)-2-((R)-azido(phenyl)methyl)-1-benzylpyrrolidine
• 英文别名: (2S)-2-[(R)-azido(phenyl)methyl]-1-benzylpyrrolidine
• CAS: 1448991-14-7
• 化学式: C₁₈H₂₀N₄
• 分子量: 292.384
• InChiKey: XLQRWHTVOJKXRX-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-((R)-azido(phenyl)methyl)-1-benzylpyrrolidine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 51.0h， 生成 1-{(R)-[(S)-1-benzylpyrrolidin-2-yl](phenyl)methyl}-3-phenylthiourea
  参考文献：
  名称：

  Synthesis of Versatile Bifunctional Derivatives of Chiral Diamines Obtained through Anchimerically Assisted Nucleophilic Substitution Reactions on Diastereomeric Phenylprolinols

  摘要：

  Diastereomeric [(S)-1-benzylpyrrolidin-2-yl]-(R)-[(phenyl)methanamine] and [(S)-1-benzylpyrrolidin-2-yl]-(S)-[(phenyl)methanamine], were synthesized by selective internal backside nucleophilic substitution of the corresponding activated phenylprolinols. X-Ray diffraction structures of crystalline acetamide derivatives confirmed the anticipated stereochemistry for a S(N)ib reaction mechanism. In order to apply this reaction to the synthesis of bifunctional analogs, a series of fragments such as a thiourea moiety and sulfonamide functions were introduced for the functionalization of the primary amino group in the substrate, obtaining more stable and potentially useful derivatives.

  DOI：

  10.3987/com-12-s(n)82
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 叠氮磷酸二苯酯 、 二异丁基氢化铝 、 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 (S)-2-((R)-azido(phenyl)methyl)-1-benzylpyrrolidine
  参考文献：
  名称：

  l-脯氨酸衍生的双功能有机催化剂：二硫代丙二酸酯对反-β-硝基烯烃的对映选择性迈克尔加成

  摘要：

  报道了一系列新颖的1-脯氨酸衍生的叔胺双官能有机催化剂9，其被用于将二硫代丙二酸酯2不对称地迈克尔加成到反式-β-硝基烯烃1上。反应以高产率（最高99％）和高对映选择性（最高97％ee）进行。这种方法的合成效用在高产率的（R）-苯酚的短合成中得到了证明。

  DOI：

  10.1021/acs.joc.6b00218

文献信息

• 화합물, 이를 이용하는 비대칭 마이클 첨가 반응을 이용한 화합물의 제조 방법, 및 페니버트 화합물의 제조 방법
  申请人：Research ＆ Business Foundation SUNGKYUNKWAN UNIVERSITY 성균관대학교산학협력단(220050013604) BRN ▼101-82-12009

  公开号：KR20180029618A

  公开（公告）日：2018-03-21

  본 발명의 화합물, 이를 이용하는 비대칭 마이클 첨가 반응을 이용한 화합물의 제조 방법, 및 페니버트 화합물의 제조 방법에서, 본 발명의 화합물은 하기 화학식 1로 나타낸다; [화학식 1] 상기 화학식 1에서, L은 또는 를 나타내고(이때, X는 황 또는 산소를 나타낸다), R은 수소, 탄소수 1 내지 5을 갖는 알킬기, 탄소수 6 내지 12을 갖는 아릴기 또는 벤질기를 나타내며, R는 탄소수 6 내지 12를 갖는 아릴기를 나타내고, R은 수소 또는 탄소수 1 내지 12를 갖는 아릴기를 나타내되, R, R 및 R의 수소들은 각각 독립적으로 탄소수 1 내지 5를 갖는 알킬기로 치환될 수 있다.

  本发明的化合物，以及使用该化合物进行的不对称迈克尔加成反应的制备方法，以及芬尼尔化合物的制备方法中，本发明的化合物表示为以下化学式1；[化学式1] 在上述化学式1中，L表示氮或氧（此时，X表示硫或氧），R表示氢，具有1到5个碳的烷基，具有6到12个碳的芳基或苄基，R表示具有6到12个碳的芳基，R表示氢或具有1到12个碳的芳基，R，R和R的氢可以分别独立地被具有1到5个碳的烷基取代。
• <scp>l</scp>-Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to <i>trans</i>-β-Nitroolefins
  作者：Hui Jin、Seung Tae Kim、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1021/acs.joc.6b00218

  日期：2016.4.15

  A series of novel l-proline derived tertiary amine bifunctional organocatalysts 9 are reported, which were applied to the asymmetric Michael addition of dithiomalonates 2 to trans-β-nitroolefins 1. The reaction proceeded in high yields (up to 99%) with high enantioselectivities (up to 97% ee). The synthetic utility of this methodology was demonstrated in the short synthesis of (R)-phenibut in high

  报道了一系列新颖的1-脯氨酸衍生的叔胺双官能有机催化剂9，其被用于将二硫代丙二酸酯2不对称地迈克尔加成到反式-β-硝基烯烃1上。反应以高产率（最高99％）和高对映选择性（最高97％ee）进行。这种方法的合成效用在高产率的（R）-苯酚的短合成中得到了证明。
• Synthesis of Versatile Bifunctional Derivatives of Chiral Diamines Obtained through Anchimerically Assisted Nucleophilic Substitution Reactions on Diastereomeric Phenylprolinols
  作者：Eusebio Juaristi、Jorge Vargas-Caporali、Carlos Cruz-Hernández

  DOI：10.3987/com-12-s(n)82

  日期：——

  Diastereomeric [(S)-1-benzylpyrrolidin-2-yl]-(R)-[(phenyl)methanamine] and [(S)-1-benzylpyrrolidin-2-yl]-(S)-[(phenyl)methanamine], were synthesized by selective internal backside nucleophilic substitution of the corresponding activated phenylprolinols. X-Ray diffraction structures of crystalline acetamide derivatives confirmed the anticipated stereochemistry for a S(N)ib reaction mechanism. In order to apply this reaction to the synthesis of bifunctional analogs, a series of fragments such as a thiourea moiety and sulfonamide functions were introduced for the functionalization of the primary amino group in the substrate, obtaining more stable and potentially useful derivatives.