2-{[1-Cyclohexyl-meth-(E)-ylidene]-amino}-3-methyl-phenol | 299898-19-4

• 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-Cyclohexyl-meth-(E)-ylidene]-amino}-3-methyl-phenol
• CAS: 299898-19-4
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: ZIXLUCBGSJKVOJ-XNTDXEJSSA-N

物化性质

• 沸点：
  374.5±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-ethylthio-1-(trimethylsiloxy)ethene 、 2-{[1-Cyclohexyl-meth-(E)-ylidene]-amino}-3-methyl-phenol 在 (S)-6,6'-dibromo-1,1'-binaphthalene-2,2'-diol 、 zirconium(IV) tert-butoxide N-甲基咪唑 、 盐酸 作用下， 生成 3-Cyclohexyl-3-(2-hydroxy-6-methyl-phenylamino)-thiopropionic acid S-ethyl ester
  参考文献：
  名称：

  Catalytic Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst

  摘要：

  DOI：

  10.1021/ja970498d
• 作为产物：
  描述：

  2-氨基-3-甲基苯酚 、 环己烷基甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 2-{[1-Cyclohexyl-meth-(E)-ylidene]-amino}-3-methyl-phenol
  参考文献：
  名称：

  The First Allylation of Imines with Allyltrichlorosilanes Using Neutral Coordinate-Organocatalysts

  摘要：

  来自醛和2-氨基苯酚的亚胺与烯丙基三氯硅烷在DMF、HMPA或吡啶N-氧化物作为中性配位有机催化剂的存在下反应，得到相应的同烯丙胺，产率高且立体选择性强；这是亚胺与烯丙基三氯硅烷发生烯丙基化的首次例子。

  DOI：

  10.1055/s-2003-41437

文献信息

• The First Enantioselective Aza-Diels-Alder Reactions of Imino Dienophiles on Use of a Chiral Zirconium Catalyst
  作者：Shū Kobayashi、Susumu Komiyama、Haruro Ishitani

  DOI：10.1002/(sici)1521-3773(19980420)37:7<979::aid-anie979>3.0.co;2-5

  日期：1998.4.20

  Chiral dihydropyridone derivatives 3 are obtained in high yields and with good enantioselectivities by the title reaction of aldimines such as 1 with Danishefsky's diene 2. 6,6'-Dibromo-1,1'-binaphthol complexes with Group 4 metals serve as catalysts; zirconium proved to be especially effective.

  手性二氢吡啶酮衍生物3可通过醛亚胺（如1）与Danishefsky's diene 2的标题反应以高收率和良好的对映选择性得到。6,6'-Dibromo-1,1'-binaphthol配合物与第4组金属配合使用；锆被证明是特别有效的。
• Enantioselective Mannich-Type Reactions Using a Novel Chiral Zirconium Catalyst for the Synthesis of Optically Active β-Amino Acid Derivatives
  作者：Haruro Ishitani、Masaharu Ueno、Shū Kobayashi

  DOI：10.1021/ja001642p

  日期：2000.8.1

  Catalytic enantioselective Mannich-type reactions of silyl enol ethers with aldimines have been successfully performed using a novel chiral zirconium catalyst prepared from zirconium(IV) tert-butoxide (Zr(OtBu)4), 2 equiv of (R)-6,6‘-dibromo-1,1‘-bi-2-naphthol ((R)-6,6‘-Br2BINOL), and N-methylimidazole. The use of aldimines having N-substituted hydroxyphenyl moieties is essential for obtaining high

  使用由锆 (IV) 叔丁醇 (Zr(OtBu)4)、2 当量 (R)-6,6' 制备的新型手性锆催化剂，已成功进行甲硅烷基烯醇醚与醛亚胺的催化对映选择性曼尼希型反应-dibromo-1,1'-bi-2-naphthol ((R)-6,6'-Br2BINOL) 和 N-甲基咪唑。使用具有 N-取代羟基苯基部分的醛亚胺对于获得高选择性至关重要，并且 N-取代基团通过氧化裂解转化为游离胺。由芳香醛以及杂环醛和脂肪醛衍生的醛亚胺与甲硅烷基烯醇醚顺利反应，以高产率和高对映选择性得到相应的β-氨基酸衍生物。已经进行了几次 NMR 实验以阐明手性 Zr 催化剂的结构以及这种不对称反应的催化循环。最后，制备了一种新的BINOL衍生物，(R)-6,6'-双(三氟甲基)-1,1'-bi-2-萘酚((R)-6,6'-(CF3)2BINOL) . 原来是秀...
• Catalytic Enantioselective Addition of Propionate Units to Imines: An Efficient Synthesis of anti--Methyl--Amino Acid Derivatives
  作者：Shū Kobayashi、Jun Kobayashi、Haruro Ishiani、Masaharu Ueno

  DOI：10.1002/1521-3765(20020916)8:18<4185::aid-chem4185>3.0.co;2-6

  日期：2002.9.16

  catalytic enantioselective addition of propionate units to simple and inert imines using a chiral zirconium complex. High reactivity and selectivity with wide substrate scope were attained by using a new chiral ligand, (R)-6,6'-bis(pentafluoroethyl)-1,1'-bi-2-naphthol ((R)-6,6'-C(2)F(5)BINOL). The reactions using geometrically isomeric ketene silyl acetals gave excellent anti-selectivity with high enantiomeric

  光学活性的抗α-甲基-β-氨基酸衍生物是基于使用手性锆配合物将丙酸酯单元催化对映选择性加成至简单和惰性亚胺而制备的。通过使用新的手性配体（R）-6,6'-双（五氟乙基）-1,1'-bi-2-萘酚（（R）-6,6' -C（2）F（5）BINOL）。在两种情况下，使用几何异构体乙烯酮甲硅烷基缩醛进行的反应均具有出色的抗选择性和高对映体过量。通过制备各种抗α-甲基-β-氨基酸和反式3，4-二取代的β-内酰胺衍生物已经证明了该反应的合成效用。
• Phenol-Directed Enantioselective Allylation of Aldimines and Ketimines
  作者：Philippe M. A. Rabbat、S. Corey Valdez、James L. Leighton

  DOI：10.1021/ol062589y

  日期：2006.12.1

  Phenols are effective directing and activating groups for our allylchlorosilane reagents, allowing the highly enantioselective allylation of a range of 2-aminophenol-derived aldimines. When the phenol is incorporated into the substrate ketimines may be allylated highly enantioselectively, leading to the experimentally simple synthesis of a range of tertiary carbinamine structures.
• Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch
  作者：John D. Huber、James L. Leighton

  DOI：10.1021/ja076035h

  日期：2007.11.28

  The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.