1-Phenyl-3-phenylaminopropanol | 15145-58-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-Phenyl-3-phenylaminopropanol
• 英文别名: N-phenyl-3-phenyl-3-hydroxypropylamine；1-phenyl-3-(phenylamino)propan-1-ol；3-Anilino-1-phenylpropan-1-ol
• CAS: 15145-58-1
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: IFNGKHFKHCGFQB-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  415.4±38.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Phenyl-3-phenylaminopropanol 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以67%的产率得到2-chloro-3,6-diphenyltetrahydro-1,3,2-oxazaphosphorin-2-oxide
  参考文献：
  名称：

  Intramolecular single and double hydrogen migrations in the mass spectra of substituted tetrahydro-1,3,2-oxazaphosphorin-2-oxides

  摘要：

  AbstractThe mass spectral fragmentation of substituted tetrahydro‐1,3,2‐oxazaphosphorin‐2‐oxides occurs by the cleavage of ring bonds. The ions due to simple cleavage, single and double hydrogen migration, seem to be triggered by CO bond cleavage of the oxazaphosphorin ring. The variations in the relative abundance of ions arising due to similar fragmentation modes have been found to depend on the nature of the substituent and the stability of the particular fragment. The single hydrogen transfer process is supported by metastable ion and shift techniques.

  DOI：

  10.1002/oms.1210181107
• 作为产物：
  描述：

  3-anilino-3-methylthio-1-phenylprop-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以74%的产率得到1-Phenyl-3-phenylaminopropanol
  参考文献：
  名称：

  Balu; Bhat; Ila, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 2, p. 250 - 255

  摘要：

  DOI：

文献信息

• Functionalized Organolithium Compounds by DTBB-Catalyzed Sulfur-Lithium Exchange
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1055/s-1999-3426

  日期：1999.3

  The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1, 4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78 °C leads to the formation of the corresponding β-γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t-BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78 °C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

  β-或γ-羟基或氨基苯硫醚（1, 4）与丁基锂和过量锂粉在催化量的DTBB存在下，在-78°C的THF中连续反应，分别生成相应的β-γ-功能化有机锂化合物2或5。这些化合物与不同的亲电试剂[D2O, t-BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO]在-78°C至室温范围内的温度下处理后，经水解，以完全区域选择性的方式分别得到预期的功能化醇或胺3或6。
• β-Functionalised organolithium compounds through a sulfur-lithium exchange
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1016/s0040-4039(97)01008-3

  日期：1997.7

  The successive reaction of different β-hydroxy or β-amino thioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTBB in THF at −78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, ButCHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between −78 and 20°C yields,

  不同的β-羟基或β-氨基硫醚1a-d与正丁基锂，过量的锂粉和催化量的DTBB在-78°C的THF中连续反应导致形成相应的β-官能化有机锂化合物2A-d ，其通过与亲电子数[d反应2 O，卜吨CHO，苯甲醛中，Me 2 CO，（CH 2）5 CO]在温度范围-78至20℃之间的产率，用水解后水，预期的功能化醇或胺3aa-de（区域选择性）。
• C−N Coupling between Aryl Azides and Cyclopropanols by Photoredox/Copper Dual Catalysis
  作者：Wu‐Jie Lin、Yu‐Zhao Wang、Wei Yu

  DOI：10.1002/adsc.202301203

  日期：2024.4.9

  photoredox/copper co-catalyzed ring-opening cross-coupling of aryl azides with cyclopropanols has been developed with fac-Ir(ppy)3 as the photocatalyst. The reaction involves intermediacy of the anilino radical generated through reduction of the azido group by fac-Ir(ppy)3* and [CuII]-enabled oxidative ring-opening of the cyclopropanol. An array of β-aminoketone compounds were synthesized under redox-neutral

  以 fac-Ir(ppy)3 作为光催化剂，开发了芳基叠氮化物与环丙醇的光氧化还原/铜共催化开环交叉偶联。该反应涉及通过 fac-Ir(ppy)3* 还原叠氮基而产生的苯胺自由基的中介作用以及 [CuII] 使环丙醇氧化开环。使用该方法在氧化还原中性条件下合成了一系列β-氨基酮化合物。
• N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo00090a044

  日期：1994.6

  The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 degrees C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents [H2O, D2O, Me(2)S(2), Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(5)CO, (EtO)(2)CO, CH2=CHCO(2)Me, PhCON(CH2)(4), PhCH=NPh, MeI, and CH2=CHCH2Br] to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5. When the reductive opening and the reaction with electrophiles [H2O, D2O, CH2=CHCH2Br, Me(2)CO, (c-C3H5)(2)CO] were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
• Borisova, E. Ya.; Sitsun', Van; Moskovkin, A. S., Russian Journal of Organic Chemistry, 1993, vol. 29, # 11.2, p. 1871 - 1875
  作者：Borisova, E. Ya.、Sitsun', Van、Moskovkin, A. S.、Golovkov, P. V.、Tubashova, I. A.、Cherkashin, M. I.

  DOI：——

  日期：——