2-{1'-[(1'S)-1'-phenylethyl]imino}phenylethanone | 1262406-40-5

• 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: 2-{1'-[(1'S)-1'-phenylethyl]imino}phenylethanone
• CAS: 1262406-40-5
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: JMLWFAUVYNJBSF-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-{1'-[(1'S)-1'-phenylethyl]imino}phenylethanone 在 palladium dihydroxide 、 palladium on activated charcoal lithium aluminium tetrahydride 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、2.03 MPa 条件下， 反应 58.17h， 生成 (1S,3R,4R)-2-Azabicyclo[2.2.1]heptane-3-(R)-phenylmethanol N,O-carbamate
  参考文献：
  名称：

  A Theoretical and Experimental Study of the Asymmetric Addition of Dialkylzinc toN-(Diphenylphosphinoyl)benzalimine

  摘要：

  The mechanism of the enantioselective addition of diethylzinc to N(diphenylphosphinoyl)benzalimine with catalysis by bicyclic 2-azanorbornyl-3-methanols was studied by quantum chemical calculations. The mechanism proved to differ from that of the addition of diethylzinc to aldehydes and also from an earlier proposed mechanism. The results of the calculations were used to identify several factors responsible for the selectivity. The theoretical evaluation was performed in connection with an experimental study of the effects of introducing an additional stereocenter in the ligand. An efficient route to both diastereomers of new bicyclic 2-azanorbornyl-3-methanols with an additional chiral center (the secondary alcohol group) is also presented. In the best case, an enantiomeric excess of up to 97% was obtained with these new ligands.

  DOI：

  10.1002/(sici)1521-3765(19990604)5:6<1692::aid-chem1692>3.0.co;2-m
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 3,4-二羟基苯乙酮 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-{1'-[(1'S)-1'-phenylethyl]imino}phenylethanone
  参考文献：
  名称：

  芳基乙二醛衍生的α-亚氨基酮与（三氟甲基）三甲基硅烷的反应；β-氨基-α-三氟甲醇的新途径

  摘要：

  在室温下，在催化量的CsF存在下，芳基乙二醛衍生的α-亚氨基酮与（三氟甲基）三甲基硅烷（CF 3 SiMe 3）在DME溶液中反应，生成O-甲硅烷基化的β-亚氨基醇。化学选择性方式。随后在乙醇溶液中用NaBH 4还原这些产物可得到相应的β-（N-烷基）氨基-α-三氟甲基醇，收率良好至极佳。对映体纯的α-亚氨基酮（Ar = Ph或p -MeOC 6 H 4）的三氟甲基化，带有手性助剂，PhCH（Me）基团连接到氮原子上，产生非对映体产物的混合物，其比例为约3。3：2。

  DOI：

  10.1016/j.jfluchem.2010.07.012

文献信息

• Garry, Scott W.; Neilson, Douglas G., Journal of the Chemical Society. Perkin transactions I, 1987, p. 601 - 606
  作者：Garry, Scott W.、Neilson, Douglas G.

  DOI：——

  日期：——
• An investigation towards the diastereoselective synthesis of 3-acetoxy/methoxy/phthalimido-β-lactams using chiral imines
  作者：Aman Bhalla、Garima Modi、S.S. Bari、Anu Kumari、Dipika Narula、Shiwani Berry

  DOI：10.1016/j.tetasy.2016.12.007

  日期：2017.2

  The efficient diastereoselective synthesis of 3-acetoxy/methoxy/phthalimido-beta-lactams 2/2', 3/3' and 4/4' respectively was performed using chiral imines 1 obtained from chiral amines. Factors (solvent, temperature, substituent, steric bulk) influencing the stereoselectivity and the diastereomeric ratio were also studied in detail. The diastereoselectivity of the two isomers was determined from the ratio of integral values of doublets of C3-H and C4-H and from the integral values of H in -CH(Me/Et)Ph/Np of the two diastereomers. Representative pairs of cis-diastereomers were separated by efficient column chromatography. (C) 2016 Elsevier Ltd. All rights reserved.