7-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane

• 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: 7-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane
• 英文别名: N-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane；[(1S,6R)-7-azabicyclo[4.1.0]heptan-7-yl]-[3,5-bis(trifluoromethyl)phenyl]methanone
• 化学式: C₁₅H₁₃F₆NO
• 分子量: 337.265
• InChiKey: KVHAZPLQZIOCAT-HMHKETEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane 、 苯基硫三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 以86%的产率得到(1R,2R)-1-phenylthio-2-[N-(3,5-bis-trifluoromethylbenzoyl)amino]cyclohexane
  参考文献：
  名称：

  Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines

  摘要：

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.

  DOI：

  10.1021/ol901209n
• 作为产物：
  描述：

  chloroamine-T 在 四丁基溴化铵 、 碘 、 sodium naphthalenide 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 36.25h， 生成 7-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines

  摘要：

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

  DOI：

  10.1021/jo401267j

文献信息

• Enantioselective desymmetrization of meso-aziridines with aromatic thiols catalyzed by chiral bifunctional quaternary phosphonium salts derived from α-amino acids
  作者：Jiaxing Zhang、Dongdong Cao、Hongyu Wang、Gang Zhao、Yongjia Shang

  DOI：10.1016/j.tet.2015.02.001

  日期：2015.3

  Desymmetrization of meso-aziridines with aromatic thiols was realized by using alpha-amino acids-derived chiral quaternary phosphonium salts catalysts to provide chiral beta-amino sulfides with high yields (up to 99%) and in moderate enantioselectivities (up to 70%). (C) 2015 Elsevier Ltd. All rights reserved.
• Brønsted Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines
  作者：Emily B. Rowland、Gerald B. Rowland、Edwin Rivera-Otero、Jon C. Antilla

  DOI：10.1021/ja0751779

  日期：2007.10.1

  The enantioselective ring-opening of meso-aziridines with azide nucleophiles; proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.
• Scalable Synthesis of <i>N</i>-Acylaziridines from <i>N</i>-Tosylaziridines
  作者：Heather Rubin、Jennifer Cockrell、Jeremy B. Morgan

  DOI：10.1021/jo401267j

  日期：2013.9.6

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.
• Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of <i>meso</i>-Aziridines
  作者：Giorgio Della Sala、Alessandra Lattanzi

  DOI：10.1021/ol901209n

  日期：2009.8.6

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.