Benzoic acid, 4-[[(4-methylphenyl)methylene]amino]-, methyl ester | 59853-02-0

• 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: Benzoic acid, 4-[[(4-methylphenyl)methylene]amino]-, methyl ester
• 英文别名: methyl 4-[(4-methylphenyl)methylideneamino]benzoate
• CAS: 59853-02-0
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: VSUBQWICIGBFIM-UHFFFAOYSA-N

物化性质

• 沸点：
  399.5±35.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-异喹啉硼酸 、 Benzoic acid, 4-[[(4-methylphenyl)methylene]amino]-, methyl ester 在 [RuH2(PPh3)4] 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以91%的产率得到4-<<4'-(methoxycarbonyl)phenyl>amino>-2-cyano-2-methyl-3-p-tolylpropanenitrile
  参考文献：
  名称：

  Ruthenium-catalyzed aldol and Michael reactions of nitriles. Carbon-carbon bond formation by .alpha.-C-H activation of nitriles.

  摘要：

  The ruthenium(II)-catalyzed reaction of nitriles with carbonyl compounds proceeds highly efficiently under neutral and mild conditions to give alpha,beta-unsaturated nitriles. Under similar reaction conditions, nitriles react with olefins bearing electron-withdrawing groups to give the corresponding Michael adducts. The efficiency of the reaction is illustrated by the selective additions to alpha,beta-unsaturated aldehydes and acetylenes bearing electron-withdrawing groups, which are difficult to perform using conventional bases. Chemoselective aldol and Michael reactions of nitriles can be performed in the presence of other active methylene compounds. Tandem Michael and Michael-aldol condensations of nitriles 30 can be performed with high diastereoselectivity. These reactions can be rationalized by assuming oxidative addition of ruthenium(0) to the alpha=C-H bond of nitriles and subsequent insertions to carbonyl compounds or olefins. As the key intermediates and active catalysts hydrido(N-bonded enolato)ruthenium(II) complexes, mer-RuH(NCCHCO(2)R)(NCCH(2)CO(2)R)(PPh(3))(3) (R = Me (41a), Et (41b), n-Bu (41c) have been upon treatment of RuH2(PPh(3))(4) (3) or RuH(C2H4)(PPh(3))(2)(PPh(2)C(6)H(4)) (4) with alkyl cyanoacetates. Kinetic study of the catalytic aldol reaction of ethyl cyanoacetate with benzaldehyde indicates that the rate-determining step reaction of enolato complex 41 with aldehydes.

  DOI：

  10.1021/ja00155a008

文献信息

• Reactions of an Arylrhodium Complex with Aldehydes, Imines, Ketones, and Alkynones. New Classes of Insertion Reactions
  作者：Christopher Krug、John F. Hartwig

  DOI：10.1021/om0496582

  日期：2004.9.1

  metalation of the resulting ketimine. The reaction of 2a with 3a-Ph was first order in arylrhodium complex and inverse first order in the concentration of pyridine. Aldehydes that cannot enolize, such as PhCHO and Me3CCHO, inserted into the Rh−aryl bond of 2a to form ketones and esters. The esters were formed from insertion of a second aldehyde into the Rh−O bond of an intermediate alkoxide, followed by

  通式Organorhodium络合物（DPPE）的Rh（吡啶）（R）（R = p -tol（图2a）和CH 2森达3（图2b），DPPE = 1,2-双（二苯基膦基）乙烷）得自制备（DPPE）Rh（μ-Cl）] 2，吡啶和对甲苯基锂或Me 3 SiCH 2 MgCl。配合物2a插入了贫电子的亚胺（p - tol）CH N（C 6 H 4 - p -CO 2 Me）（3a-Tol）和（Ph）CH N（C 6 H 4 - p-CO 2 Me）（3a-Ph）得到酰胺络合物，可直接分离或用PEt 3捕集。相反，芳基配合物2a与电子中性和电子富集的亚胺PhCH NPh（3b）和（p- tol）CH N（C 6 H 4 - p -OMe）（3c）反应没有形成稳定的酰胺产品。相反，将来自亚胺3b或3c插入的酰胺进行β-氢消除，然后将所得的酮亚胺金属化。2a与3a-Ph的反应在芳基铑络合物中为一阶，在吡啶
• Imine Insertion into a Late Metal−Carbon Bond To Form a Stable Amido Complex
  作者：Christopher Krug、John F. Hartwig

  DOI：10.1021/ja038819a

  日期：2004.3.1

  appeared to involve insertion, but the amido complexes formed from these insertions were not stable. Thus, reaction of 2 with 3b, followed by addition of Et3NHCl, gave the amine and ketimine products (Ph)(p-tol)CH-NHPh, 5, and (p-tol)(Ph)C=N(Ph), 6, in 25% and 50% yields. Several lines of data indicate that these products are formed by a sequence of transformations involving insertion of imine to give

  制备了含有不稳定配位体的芳基铑 (I) 配合物，并研究了其对芳基亚胺的反应性。芳基铑 (I) 络合物 (DPPE)Rh(C5H5N)(p-tol), 2 以 65% 的产率从 [(DPPE)Rh(mu-Cl)]2、吡啶和对甲苯基锂中分离出来。2与醛亚胺(p-tol)CH=N(C6H4-p-CO2Me)(3a-Tol)的反应以88%的分离产率得到Rh酰胺插入产物4。4 的固态结构是通过单晶 X 射线衍射确定的。2 与电子中性和富电子醛亚胺 (Ph)CH=NPh (3b) 和 (p-tol)CH=N(C6H4-p-OMe) (3c) 的反应似乎也涉及插入，但由这些插入形成的酰氨基复合物不稳定。因此，2 与 3b 反应，然后加入 Et3NHCl，得到胺和酮亚胺产物 (Ph)(p-tol)CH-NHPh, 5，和 (p-tol)(Ph)C=N(Ph)， 6、收益率分别为 25% 和 50%。几行数
• Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
  作者：OM Walsh、MJ Meegan、RM Prendergast、T Al Nakib

  DOI：10.1016/s0223-5234(97)86178-8

  日期：1996.1

  The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
• Nickel Catalyzed Imine Aldol Reactions between Activated Imines and Pronucleophiles
  作者：N Shida

  DOI：10.1016/00404-0399(50)0912v-

  日期：1995.7.10

  Treatment of activated imines 1 with carbonyl compounds 2 in the presence of catalytic amounts of NiCl2(PPh(3))(2) or NiBr2(PPh(3))(2) at room temperature affords imine aldol products 3 in high to good yields.
• LIQUID CRYSTAL MATERIAL, LIQUID CRYSTAL DISPLAY DEVICE AND LIQUID CRYSTAL DISPLAY
  申请人：Shibahara Seiji

  公开号：US20090168009A1

  公开（公告）日：2009-07-02

  A liquid crystal display device capable of obtaining good display characteristics and good response characteristics is provided. A liquid crystal material being a paraelectric material, the liquid crystal material includes: a liquid crystal molecule exhibiting a nematic liquid crystal phase at room temperature and including one or more cyclic structures; and a bent-shaped molecule including cyclic structures which are large in number compared to the cyclic structures included in the liquid crystal molecule.