tert-butyl ((S)-3,3-dimethyl-1-oxo-1-((R)-2-(pyren-4-yl)pyrrolidin-1-yl)butan-2-yl)carbamate | 1222923-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: tert-butyl ((S)-3,3-dimethyl-1-oxo-1-((R)-2-(pyren-4-yl)pyrrolidin-1-yl)butan-2-yl)carbamate
• CAS: 1222923-27-4
• 化学式: C₃₁H₃₆N₂O₃
• 分子量: 484.638
• InChiKey: LQXWKEWZNBHFNX-SHQCIBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-3,3-dimethyl-1-oxo-1-((R)-2-(pyren-4-yl)pyrrolidin-1-yl)butan-2-yl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 C₂₆H₂₈N₂O
  参考文献：
  名称：

  Enantioselective Selenocyclization via Dynamic Kinetic Resolution of Seleniranium Ions by Hydrogen-Bond Donor Catalysts

  摘要：

  Highly enantioselective selenocyclization reactions are promoted by the combination of a new chiral squaramide catalyst, a mineral acid, and an achiral Lewis base. Mechanistic studies reveal that the enantioselectivity originates from the dynamic kinetic resolution of seleniranium ions through anion-binding catalysis.

  DOI：

  10.1021/ja510113s
• 作为产物：
  描述：

  N-Boc-L-叔亮氨酸 、 (R)-2-(4-pyrenyl)pyrrolidine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以83%的产率得到tert-butyl ((S)-3,3-dimethyl-1-oxo-1-((R)-2-(pyren-4-yl)pyrrolidin-1-yl)butan-2-yl)carbamate
  参考文献：
  名称：

  Enantioselective Thiourea-Catalyzed Cationic Polycyclizations

  摘要：

  A new thiourea catalyst is reported for the enantioselective cationic polycyclization of hydroxylactams. Both the yield and enantioselectivity of this transformation were found to vary strongly with the identity of a single aromatic residue on a common catalyst framework, with more expansive and polarizable arenes proving optimal. Evidence is presented for a mechanism in which stabilizing cation-Pi interactions are a principal determinant of enantioselectivity.

  DOI：

  10.1021/ja101256v

文献信息

• Enantioselective Thiourea-Catalyzed Intramolecular Cope-Type Hydroamination
  作者：Adam R. Brown、Christopher Uyeda、Carolyn A. Brotherton、Eric N. Jacobsen

  DOI：10.1021/ja402893z

  日期：2013.5.8

  Catalysis of Cope-type rearrangements of bis-homoallylic hydroxylamines is demonstrated using chiral thiourea derivatives. This formal intramolecular hydroamination reaction provides access to highly enantioenriched alpha-substituted pyrrolidine products and represents a complementary approach to metal-catalyzed methods.