1-(4-{[(4-chlorophenyl)methylene]amino}phenyl)ethanone | 32884-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-{[(4-chlorophenyl)methylene]amino}phenyl)ethanone
• 英文别名: N-(p-chlorobenzylidene)-p-aminoacetophenone；4-Acetyl-N-(4-chlorobenzylidene)aniline；4'-(4-Chlorobenzylideneamino)acetophenone；1-[4-[(4-chlorophenyl)methylideneamino]phenyl]ethanone
• CAS: 32884-52-9
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: HBIOGMSFDFPLMI-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C
• 沸点：
  415.7±30.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  1-(4-{[(4-chlorophenyl)methylene]amino}phenyl)ethanone 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 N-{4-[(E)-3-(4-Nitro-phenyl)-acryloyl]-phenyl}-2-piperidin-1-yl-acetamide
  参考文献：
  名称：

  Fahmy, A. M.; Hassan, Kh. M.; Khalaf, A. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 884 - 887

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醛 、 4-氨基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-(4-{[(4-chlorophenyl)methylene]amino}phenyl)ethanone
  参考文献：
  名称：

  新型烯胺衍生物的合成、抗增殖、细胞毒活性、DNA结合特征和分子对接研究

  摘要：

  通过内酯和查耳酮的反应合成了新的烯胺衍生物，并研究了它们对六种癌细胞系（例如 HeLa、HT29、A549、MCF7、PC3 和 Hep3B）和一种正常细胞系（例如，FL）的抗增殖和细胞毒活性以及它们与 CT-DNA 的相互作用模式。大多数 IC50 值为 86-168 μM 的烯胺衍生物表现出比起始分子更强的抗癌细胞增殖活性。虽然在烯胺衍生物中，四种化合物对 Hep3B 细胞系显示出比对照药物（5-氟尿嘧啶和顺铂）更高的细胞毒性效力，但这些化合物对正常细胞 FL 没有表现出任何显着的毒性。UV/VIS 光谱数据表明，八种化合物会导致具有轻微红移（~6 nm）的低色度，表明它们通过嵌入或小沟结合模式与 DNA 结合。化合物的结合常数在0.1×103 M-1–2.3×104 M-1范围内。所研究的烯胺衍生物的抗增殖活性可能是由于它们的 DNA 结合以及它们的细胞毒特性。除了这些测定之外，还通

  DOI：

  10.1002/cbdv.202000139

文献信息

• Chemoselectivity in reactions of an α-diazo-β-diketone with some conjugative double-bond systems
  作者：Jiaxi Xu、Qihan Zhang、Liangbi Chen、Hui Chen

  DOI：10.1039/b103173m

  日期：——

  Reactions of 2-diazo-1,3-diphenylpropane-1,3-dione with α,β-unsaturated aldehydes and ketones, and keto-imines, in refluxing anhydrous toluene indicate that benzoyl(phenyl)ketene, which is generated by the thermal Wolff rearrangement of 2-diazo-1,3-diphenylpropane-1,3-dione, shows a pronounced tendency to form chemospecific [2 + 4] Diels–Alder adducts with the carbonyl group in α,β-unsaturated aldehydes and ketones, and the imine group in keto-imines. The reactivity in reactions of the α-diazo-β-diketone with these conjugative double-bond systems is CN > CO > CC. However, benzoyl(phenyl)ketene reacts with α,β-unsaturated imines to produce chemospecific [2 + 2] cycloadducts: β-lactams.

  2-二氮基-1,3-二苯基丙烯-1,3-二酮与α,β-不饱和醛和酮以及酮亚胺在回流无水甲苯中的反应表明，通过热的沃尔夫重排生成的苯甲酰（苯基）烯酮，显示出与α,β-不饱和醛和酮中的羰基及酮亚胺中的亚胺基形成化学特异性[2+4]戴尔斯-阿尔德加合物的显著倾向。α-二氮基-β-二酮与这些共轭双键体系的反应活性顺序为CN > CO > CC。然而，苯甲酰（苯基）烯酮与α,β-不饱和亚胺反应生成化学特异性[2+2]环加合物：β-内酰胺。
• Design, Synthesis and In Vitro Antimalarial Evaluation of New Quinolinylhydrazone Derivatives
  作者：Le Thi Thuy、Hoang Xuan Tien、Vu Dinh Hoang、Tran Khac Vu

  DOI：10.2174/157018012799079815

  日期：2012.2.1

  A series of novel quinolinylhydrazones (5a-f) was synthesized by the condensation reaction of 2,6-diarylsubstituted piperidin-4-ones (4a-f) with 7-chloro-4-hydrazinoquinoline (2). Novel quinolinylhydrazones containing Shiff bases 8a-f and 11a-f were obtained via the condensation of Shiff bases 7a-f and 10a-f with 7-chloro-4-hydrazinoquinoline. These synthesized hydrazones were screened for their in vitro antimalarial activities to chloroquine - sensitive (T96) and chloroquine – resistant (K1) strains of P.falciparum. Among the synthesized compounds, 11a exhibited strong antimalarial activity at IC50 of 103.4 ng/mL and 18.76 ng/mL to both strains of P.falciparum, respectively.

  合成了一系列新型喹啉乙肼酮（5a-f），通过2,6-二芳基取代的哌啶-4-酮（4a-f）与7-氯-4-羟基喹啉（2）的缩合反应获得。通过7a-f和10a-f的Schiff碱与7-氯-4-羟基喹啉的缩合，获得了包含Schiff碱的新型喹啉乙肼酮8a-f和11a-f。这些合成的乙肼酮对氯喹敏感（T96）和氯喹耐药（K1）型恶性疟原虫（P.falciparum）进行了体外抗疟活性筛选。在合成的化合物中，11a对两种P.falciparum株表现出强的抗疟活性，其IC50分别为103.4 ng/mL和18.76 ng/mL。
• Determination of Latent Transition Temperatures of Nonmesomorphs by Extrapolation Method in Binary Systems
  作者：A. V. Doshi、U. C. Bhoya、J. J. Travadi

  DOI：10.1080/15421406.2011.591663

  日期：2012.1.1

  Eight binary systems consisting of mesomorphs and nonmesomorphs (A(1) or A(2), + B-1, B-2, ... B-7, B-8) were studied with a view to determine the latent transition temperature (LTT) for the nonmesomorphic component (B) of a binary system by an extrapolation method. Encouraging results supporting earlier views and LTT values were obtained for seven binary systems. Instead of reporting a single value of LTT, the range of temperature or two or three values are reported herewith depending upon the possible paths of extrapolation. LTT reported earlier for nonmesomorphs lie within the range of temperature determined presently. Though the "group slope value" differs from the earlier reported value, the group efficiency order remains the same. Thus, the present investigation raises the credibility of an extrapolation method to determine LTT and group efficiency order for nematic mesophase. Component A(1) and A(2) are nematogenic, namely, p-(p'-n-propyloxy benzoyloxy) anisole (A(1)) (90.0 to 116.0) and p-(p'-n-butyloxy benzoyloxy) anisole (A(2)) (116.0 to 105.5). B-1 to B-8 are Schiff's bases. Transition and melting temperatures are observed through hot stage polarizing microscope for binary mixtures and pure components.
• Doshi, A.V.; Joshi, N.N., Journal of the Indian Chemical Society, 1993, vol. 70, # 10, p. 807 - 810
  作者：Doshi, A.V.、Joshi, N.N.

  DOI：——

  日期：——
• Sidhu, Anjali; Sharma; Rai, Mangat, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 247 - 250
  作者：Sidhu, Anjali、Sharma、Rai, Mangat

  DOI：——

  日期：——