Phenol, 2-[(E)-[[(1S)-1-phenylethyl]imino]methyl]- | 69350-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Phenol, 2-[(E)-[[(1S)-1-phenylethyl]imino]methyl]-
• 英文别名: N-(2-hydroxybenzylidene)-(S)-phenylethylamine；(S,E)-2-{[1-(phenylethyl)imino]methyl}phenol；(S,E)-2-((1-phenylethylimino)methyl)phenol；(S)-N-(1-phenylethyl)salicylideneamine
• CAS: 69350-14-7
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: KXFHUWSZKOXLFW-JASJWYONSA-N

物化性质

• 熔点：
  75-77 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  354.4±35.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Phenol, 2-[(E)-[[(1S)-1-phenylethyl]imino]methyl]- 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以64%的产率得到(S)-o-(1-phenylethylaminomethyl)phenol
  参考文献：
  名称：

  Enantioselective cyclopropanation of 1,1-diphenylethylene and diazoacetic acid ester with copper catalysts

  摘要：

  DOI：

  10.1007/bf00809355
• 作为产物：
  描述：

  水杨醛 生成 Phenol, 2-[(E)-[[(1S)-1-phenylethyl]imino]methyl]-
  参考文献：
  名称：

  DESIMONI, G.;QUADRELLI, P.;RIGHETTI, P. P., TETRAHEDRON, 46,(1990) N, C. 2927-2934

  摘要：

  DOI：
• 作为试剂：
  描述：

  diethylzinc 、 苯甲醛 在 Phenol, 2-[(E)-[[(1S)-1-phenylethyl]imino]methyl]- 作用下， 以 正己烷 、 甲苯 为溶剂， 生成 (R)-(+)-1-苯基-1-丙醇 、 S(-)-1-苯基-1-丙醇
  参考文献：
  名称：

  衍生自 (S)-α-甲基苄胺的双齿席夫碱作为二乙基锌与醛的电子控制不对称加成中的手性配体

  摘要：

  合成了一组衍生自对映体纯 (S)-α-甲基苄胺的双齿席夫碱。确定了三种化合物的晶体结构。在 Et2Zn 与醛的不对称加成过程中，席夫碱用作手性配体。取决于底物，获得的对映选择性为 ee = 8-94%，并且对于 (S,E)-2-(1-(1-苯基乙基亚氨基)-乙基)苯酚观察到最佳。对映选择性的增加与底物分子中取代基诱导的电子效应有关。分子建模产生了含有研究的席夫碱的 Zn-Zn 复合催化剂的 3D 结构模型，这与报道的加成产物的手性一致，并解释了观察到的 ee

  DOI：

  10.3998/ark.5550190.0012.914

文献信息

• Cobalt(II) catalysed reaction of alkenes with aliphatic aldehydes and molecular oxygen: scope and mechanism
  作者：Sonika Bhatia、T. Punniyamurthy、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4020(01)87194-5

  日期：1993.7

  prepared using Schiff's bases derived from aromatic aldehydes and amines or α-aminoesters. These complexes are versatile catalyst for the reaction between aliphatic aldehydes and various alkenes. The outcome of the reaction is controlled by the electronic nature of the alkene as the electron deficient alkenes undergo oxidative addition of aldehydes followed by dioxygen incorporation to yield 2-hydr

  可以使用衍生自芳族醛和胺或α-氨基酯的席夫碱制备各种钴（II）配合物。这些络合物是脂肪族醛与各种烯烃之间反应的通用催化剂。反应的结果受烯烃的电子性质控制，因为缺电子的烯烃经历醛的氧化加成反应，然后引入双氧生成2-羟基（酰氧基）-4-氧酸酯或腈，而未活化或富电子的烯烃则提供了相应的环氧化物。这些反应是通过自由基途径进行的，并提出了一种常见的酰基钴中间体，用于形成4和环氧化物7。
• Robust chiral zirconium alkoxide initiators for the room-temperature stereoselective ring-opening polymerisation of rac-lactide
  作者：Amanda J. Chmura、David M. Cousins、Matthew G. Davidson、Matthew D. Jones、Matthew D. Lunn、Mary F. Mahon

  DOI：10.1039/b716304e

  日期：——

  Chiral Schiff bases (1H to 4H) and a series of their Group 4 metal alkoxide complexes [(R-1)2Ti(OiPr)2, (R-2)2Ti(OiPr)2, (R-1)2Zr(OiPr)2, (R-2)2Zr(OiPr)2, (R-3)2Zr(OiPr)2, (R-4)2Zr(OiPr)2, (S-1)2Zr(OiPr)2 and (rac-1)2Zr(OiPr)2] have been prepared and characterised by 1H, and 13C NMR spectroscopy. In solution, both Λ and Δ isomers were observed, suggesting a low degree of chiral induction from the ligand. One ligand (R-4H) and three complexes [Δ-(R,R-2)2Ti(OiPr)2, Λ-(R,R-1)2Zr(OiPr)2 and Δ-(R,R-3)2Zr(OiPr)2] have also been characterised by single crystal X-ray diffraction. All complexes were found to have a pseudo-octahedral α-cis geometry. The complexes were tested as initiators for the ring-opening polymerisation of rac-lactide in solution and in the melt. The titanium complexes are inactive in solution and afford atactic polylactide in the melt. Zr(IV) complexes afford heterotactically enriched polylactide both in toluene solution (at 20 °C and 80 °C) and in the melt. Polymerisations were generally found to be well-controlled, giving predictable molecular weights and low molecular weight distributions. Ligand variation (substituents and/or chirality) has little effect on either the activity or selectivity of initiators. Zirconium initiators were found to be unusually robust as they were able to maintain well-controlled polymerisation following addition of water to reactions in solution and when using unpurified monomer for reactions in the melt.

  手性席夫碱（1H 至 4H）及其一系列第 4 族金属醇盐配合物 [(R-1)2Ti(OiPr)2、(R-2)2Ti(OiPr)2、(R-1)2Zr(OiPr) 2、(R-2)2Zr(OiPr)2、(R-3)2Zr(OiPr)2、(R-4)2Zr(OiPr)2、(S-1)2Zr(OiPr)2 和 (rac-1) )2Zr(OiPr)2]已被制备并通过 1H 和 13C NMR 光谱进行表征。在溶液中，观察到 Λ 和 Δ 异构体，表明配体的手性诱导程度较低。一种配体 (R-4H) 和三种配合物 [Δ-(R,R-2)2Ti(OiPr)2、Λ-(R,R-1)2Zr(OiPr)2 和 Δ-(R,R-3) 2Zr(OiPr)2]也已通过单晶X射线衍射进行了表征。发现所有配合物均具有伪八面体 α-顺式几何形状。测试了该配合物作为溶液和熔体中消旋丙交酯开环聚合的引发剂。钛配合物在溶液中不活泼，并在熔体中提供无规立构聚丙交酯。 Zr(IV) 络合物在甲苯溶液（20°C 和 80°C）和熔体中均可提供杂规富集的聚丙交酯。通常发现聚合反应受到良好控制，产生可预测的分子量和低分子量分布。配体变异（取代基和/或手性）对引发剂的活性或选择性影响很小。人们发现锆引发剂异常稳定，因为在溶液反应中添加水后以及在熔体中使用未纯化的单体进行反应时，它们能够保持良好控制的聚合反应。
• Generation of chiral bis(cyclopentadienyl)neodymium Schiff base complex bearing internal C-C bond formation and hydrogen transfer
  作者：Qiancai Liu、Mengxian Ding、Yonghua Lin、Yan Xing

  DOI：10.1016/s0022-328x(97)00463-4

  日期：1997.12

  NdCl3 reacts with excess CpNa (Cp=Cyclopentadienyl) in THF, followed by sequent treatment with (S)-(+)-N-(1-phenylethyl)salicylideneamine led to the formation of title compound, . The X-ray structure determination shows that it is a dimer with internal C-C bond formation and hydrogen transfer between one of Cp ring and the C=N bond of Schiff base ligand.

  NdCl 3与过量的CpNa（Cp =环戊二烯基）在THF中反应，然后依次用（S）-（+）- N-（1-苯乙基）水杨亚胺处理，形成标题化合物。X射线结构测定表明，它是具有内部CC键形成且Cp环之一与席夫碱配体的C ＝ N键之间的氢转移的二聚体。
• Aggregation-induced emission enhancement of chiral boranils
  作者：Patrícia A. A. M. Vaz、João Rocha、Artur M. S. Silva、Samuel Guieu

  DOI：10.1039/c8nj03228a

  日期：——

  New boranils based on chiral benzylamines have been synthesized and their photophysical properties studied. These BF2-complexes exhibit a bright blue fluorescence in solution and in the solid state, and exhibit aggregation-induced emission enhancement. The chirality of the ligand, even if it is not directly located at the boron center, has consequences on the circular dichroism of the complexes.

  已经合成了基于手性苄胺的新型硼烷，并研究了它们的光物理性质。这些BF 2-络合物在溶液中和在固态下显示出亮蓝色的荧光，并且表现出聚集诱导的发射增强。配体的手性，即使不直接位于硼中心，也会影响复合物的圆二色性。
• Oxabicyclo 3.1.0 hexanes useful in the production of cyclopropanecarboxylate insecticides and intermediate compounds
  申请人：FMC Corporation

  公开号：EP0003666A1

  公开（公告）日：1979-08-22

  The invention provides compounds of the formulae: in which R is hydrogen or CX3. each X, which is the same as or different from the other, is a chlorine or bromine atom, R' is lower alkyl or lower alkoxy, R2 is hydrogen, lower alkoxycarbonyl or lower alkanoyl, and R3 is hydrogen or lower alkoxycarbonyl. The compounds of Formula III are made by intramolecular carbenoid cyclization of compounds of Formula II; the compounds of Formula II are made from compounds of Formula I, e.g. by treatment with azide followed by a base; the compounds of Formula I are prepared by reacting an alcohol of formula: with a hydrazone. Those compounds of Formula I in which R is CX3 can be converted to a compound of the formula: in which the carboxy and dihalovinyl groups are cis with respect to each other, which are insecticidal, by treatment with certain metals in selected solvents.

  本发明提供了以下式子的化合物： 其中R为氢或CX3.与之相同或不同的各X为氯原子或溴原子，R'为低级烷基或低级烷氧基，R2为氢、低级烷氧羰基或低级烷酰基，R3为氢或低级烷氧羰基。 式 III 的化合物是通过式 II 的化合物的分子内类碳环化反应制得的；式 II 的化合物是由式 I 的化合物制得的，例如先用叠氮化物处理，再用碱处理；式 I 的化合物是通过式......的醇与腙反应制备的： 与腙反应制得。 其中 R 为 CX3 的式 I 化合物可转化为式： 其中羧基和二卤乙烯基互为顺式基团的化合物，可通过在选定溶剂中使用某些金属进行处理而获得杀虫效果。