1,1,3-triphenyl-3-(N-anilino)-1-propanol | 71912-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,1,3-triphenyl-3-(N-anilino)-1-propanol
• 英文别名: 3-anilino-1,1,3-triphenylpropan-1-ol；1,1,3-Triphenyl-3-anilinopropan-1-ol
• CAS: 71912-98-6
• 化学式: C₂₇H₂₅NO
• 分子量: 379.502
• InChiKey: GHSWUSAHRRJPSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 生成 1,1,3-triphenyl-3-(N-anilino)-1-propanol
  参考文献：
  名称：

  Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies

  摘要：

  The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields. The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in CH3CN also afforded 2a-d or 2a-b. These reactions proceed via the attack of NO on the radical cation of 1, which is formed by electron transfer from 1 to 1DCA* or NO+. The reaction of 1-alkyl-2-arylcyclopropanes with NOBF4 afforded mixtures of 3-alkyl-5-aryl-2-isoxazolines and 4-alkyl-5-aryl-2-isoxazolines via the direct attack of NO+ on the cyclopropane rings. The reaction of 1,1,2,2-tetraphenylcyclopropane with NOBF4 afforded 2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate via the migration of the phenyl group to nitrogen.

  DOI：

  10.1021/jo00043a026

文献信息

• Regio- and stereoselective double alkylation of β-enamino esters with organolithium reagents followed by one-pot reduction: convenient method for the synthesis of tertiary γ-amino alcohols
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1016/j.tet.2006.07.044

  日期：2006.10

  stereoselective procedure for the preparation of tertiary γ-amino alcohols starting from β-enamino esters is presented. In this procedure, the double alkylation of β-enamino esters with organolithium reagents is followed by one-pot reduction with sodium borohydride in methanol/acetic acid. A hypothesis of mechanism is given, explaining the observed diastereoselectivity through molecular modeling. The configuration

  提出了一种简单，高产且立体选择性的方法，该方法可从β-烯胺酯开始制备叔γ-氨基醇。在该方法中，用有机锂试剂对β-烯胺酯进行双烷基化，然后用硼氢化钠在甲醇/乙酸中一锅还原。给出了机理的假设，通过分子建模解释了观察到的非对映选择性。产物的构型通过1 H NMR光谱结合构象分析确定。
• .beta.-Substituted organolithium compounds. New reagents for synthesis
  作者：Jose Barluenga、Francisco J. Fananas、Miguel Yus

  DOI：10.1021/jo00394a011

  日期：1979.12
• BARLUENGA J.; FANANAS F. J.; YUS M., J. ORG. CHEM., 1979, 44, NO 26, 4798-4801
  作者：BARLUENGA J.、 FANANAS F. J.、 YUS M.

  DOI：——

  日期：——
• Insertion of nitrogen oxide and nitrosonium ion into the cyclopropane ring: a new route to 2-isoxazolines and its mechanistic studies
  作者：Kazuhiko Mizuno、Nobuyuki Ichinose、Toshiyuki Tamai、Yoshio Otsuji

  DOI：10.1021/jo00043a026

  日期：1992.8

  The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields. The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in CH3CN also afforded 2a-d or 2a-b. These reactions proceed via the attack of NO on the radical cation of 1, which is formed by electron transfer from 1 to 1DCA* or NO+. The reaction of 1-alkyl-2-arylcyclopropanes with NOBF4 afforded mixtures of 3-alkyl-5-aryl-2-isoxazolines and 4-alkyl-5-aryl-2-isoxazolines via the direct attack of NO+ on the cyclopropane rings. The reaction of 1,1,2,2-tetraphenylcyclopropane with NOBF4 afforded 2,3,5,5-tetraphenyl-2-isoxazolinium tetrafluoroborate via the migration of the phenyl group to nitrogen.