3-(2-naphthyl)acrylic acid chloride | 120301-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-naphthyl)acrylic acid chloride
• 英文别名: (E)-3-(naphthalen-2-yl)acryloyl chloride；3-(2-naphthyl)acryloyl chloride；trans-3-(naphth-2-yl)-acrylic acid chloride；(E)-3-(2-naphthyl)propenoyl chloride；(E)-3-naphthalen-2-ylprop-2-enoyl chloride
• CAS: 120301-63-5
• 化学式: C₁₃H₉ClO
• 分子量: 216.667
• InChiKey: IPKQVFIYJDYABU-SOFGYWHQSA-N

物化性质

• 沸点：
  367.6±11.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-naphthyl)acrylic acid chloride 在 氟化氢吡啶 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,15-trihydroxy-10,14,17,17-tetramethyl-12-[(E)-3-naphthalen-2-ylprop-2-enoyl]oxy-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Targeting FtsZ for Antituberculosis Drug Discovery:  Noncytotoxic Taxanes as Novel Antituberculosis Agents

  摘要：

  Screening of 120 taxanes identified a number of compounds that exhibited significant antituberculosis activity. Rational optimization of selected compounds led to the discovery that the C-seco-taxane-multidrug-resistance (MDR) reversal agents (C-seco-TRAs) are non-cytotoxic at the upper limit of solubility and detection (> 80 mu M), while maintaining MIC99 values of 1.25-2.5 mu M against drug-resistant and drug-sensitive strains of Mycobacterium tuberculosis (MTB). Treatment of MTB cells with TRA 3aa and 10a at the MIC caused filamentation and prolongation of the cells, a phenotypic response to FtsZ inactivation.

  DOI：

  10.1021/jm050920y
• 作为产物：
  描述：

  (E)-3-(萘-2-基)丙烯酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-(2-naphthyl)acrylic acid chloride
  参考文献：
  名称：

  高非对映选择性，有机碱催化的室温迈克尔加成反应的合理设计。

  摘要：

  通过合理设计单首选过渡态，并通过电子供体-受体型吸引相互作用使其稳定，已确定了相应起始化合物的结构和几何要求。甘氨酸的席夫碱与邻-​​[N-α-吡啶甲基氨基]苯乙酮（作为亲核甘氨酸等效物）和N-（反式-烯酰基）恶唑烷-2-酮（作为α的衍生物）的Ni（II）配合物，发现β-不饱和羧酸是具有几何/构象均质性和高反应性的选择底物。发现相应的迈克尔加成反应在室温下在催化量的DBU存在下进行，以定量提供具有几乎完全非对映选择性的加成产物。

  DOI：

  10.1021/jo0008791

文献信息

• Pd-Catalyzed α-Selective C–H Functionalization of Olefins: En Route to 4-Imino-β-Lactams
  作者：Wei-Jun Kong、Yue-Jin Liu、Hui Xu、Yan-Qiao Chen、Hui-Xiong Dai、Jin-Quan Yu

  DOI：10.1021/jacs.5b13353

  日期：2016.2.24

  Pd-catalyzed α-olefinic C-H activation of simple α,β-unsaturated olefins has been developed. 4-imino-β-lactam derivatives were readily synthesized via activation of α-olefinic C-H bonds with excellent cis stereoselectivity. A wide range of heterocycles at the β-position are compatible with this reaction. The product of 4-imino-β-lactam derivatives can be readily converted to 2-aminoquinoline which

  已经开发了 Pd 催化的 α-烯烃 CH 活化简单的 α,β-不饱和烯烃。4-亚氨基-β-内酰胺衍生物很容易通过α-烯烃CH键的活化合成，具有优异的顺式立体选择性。β-位的多种杂环与该反应相容。4-亚氨基-β-内酰胺衍生物的产物可以很容易地转化为广泛存在于药物和天然产物中的2-氨基喹啉。
• Acrylamide derivatives as antiallergic agents. I. Synthesis and structure-activity relationships of N-((4-substituted 1-piperazinyl)alkyl)-3-(aryl and heteroaryl)acrylamides.
  作者：Yoshinori NISHIKAWA、Tokuhiko SHINDO、Katsumi ISHI、Hideo NAKAMURA、Tatsuya KON、Hitoshi UNO

  DOI：10.1248/cpb.37.100

  日期：——

  A new series of acrylamide derivatives (7-10) were synthesized. Antiallergic activity of these compounds was evaluated and their structure-activity relationships were examined. Compounds 10d, N[4-(4-diphenylmethyl-1-piperazinyl)buthyl]3-(3-pyridyl)acrylamide, showed antiallergic activity equivalent or superior to that of ketotifen in the rat passive cutaneous anaphylaxis (PCA) test by oral administration. Compound 10d, unlike ketotifen, had more potent in vitro 5-lipoxygenase inhibitory activity than caffeic acid, whereas its in vitro antihistamine activity was weaker than that of ketotifen. In addition, its inhibitory activity against histamine release from rat mast cells was approximately two-thirds as potent as that of disodium cromoglycate (DSCG). Compound 10d is a promising agent for treating a variety of allergic diseases.

  一系列新的丙烯酰胺衍生物（7-10）被合成。对这些化合物的抗过敏活性进行了评估，并考察了它们的结构-活性关系。化合物10d，即N[4-(4-二苯甲基-1-哌嗪基)丁基]3-(3-吡啶基)丙烯酰胺，在口服给药的大鼠被动皮肤过敏反应（PCA）测试中显示出与酮替芬相当或更优越的抗过敏活性。与酮替芬不同，10d在体外对5-脂氧合酶的抑制活性比咖啡酸更强，而其体外抗组胺活性则弱于酮替芬。此外，它对大鼠肥大细胞释放组胺的抑制活性约为色甘酸二钠（DSCG）的三分之二。化合物10d是一种有前途的多种过敏性疾病治疗药物。
• [EN] RODENTICIDAL NORBORMIDE ANALOGUES<br/>[FR] ANALOGUES DE NORBORMIDE RODENTICIDE
  申请人：LANDCARE RES NEW ZEALAND LTD

  公开号：WO2013133726A1

  公开（公告）日：2013-09-12

  The present invention relates to norbormide analogues having rodenticidal activity; rodenticidal compositions comprising the analogues; uses of the analogues as rodenticides; uses of the analogues in the manufacture of rodenticidal compositions; and methods for controlling rodents using the compositions.

  本发明涉及具有杀鼠活性的诺波酰胺类似物；包括这些类似物的杀鼠组合物；将这些类似物用作杀鼠剂的用途；将这些类似物用于制造杀鼠组合物的用途；以及使用这些组合物控制啮齿动物的方法。
• Phenylalanine derivatives enhancing intestinal absorption of insulin in mice.
  作者：YUSUKE AMINO、KAZUHIRO KAWADA、KOJI TOI、IZUMI KUMASHIRO、KOJI FUKUSHIMA

  DOI：10.1248/cpb.36.4426

  日期：——

  The adjuvant effect of N-acyl-L-and D-phenylalanine derivatives on intestinal absorption of insulin was investigated in normal mice. The correlation between the chemical structural properties of the N-acyl moiety and the absorption-promoting activity was estimated from the glucose concentrations and the insulin levels in the blood of mice after oral combined administration of insulin and adjuvant. The chemical structural properties of N-acyl-phenylalanine derivatives necessary for adjuvant effect on intestinal absorption of insulin were as follows. 1. An aromatic ring is present, separated by two atoms from the acyl carbonyl group. 2. Either of X or Y is oxygen or X-Y is a double bond in Fig.2. 3. The N-acyl moiety has small hydrophobic substituents, such as F, Cl, or Me at Rα, Rβ, Rη and has an appropriate hydrophilic-hydrophobic balance of the overall molecule. The use of these agents to enhance insulin absorption offers the possibility of a new approach to oral insulin therapy.

  研究了N-酰基-L-和D-苯丙氨酸衍生物对正常小鼠胰岛素肠道吸收的辅助效应。根据小鼠口服胰岛素和辅料联合给药后的血糖浓度和胰岛素水平，推测了N-酰基部分的化学结构性质与促吸收活性之间的相关性。N-酰基-苯丙氨酸衍生物对胰岛素肠道吸收具有辅效应的化学结构性质如下：1. 芳环存在，与酰基羰基相隔两个原子。2. 图2中的X或Y之一为氧，或者X-Y是双键。3. N-酰基部分具有较小的疏水取代基，如F、Cl或Me在Rα、Rβ、Rη位置，并且整个分子具有适当的亲水-疏水平衡。利用这些制剂增强胰岛素吸收，为口服胰岛素治疗提供了新的途径。
• Benzo[b]pyrano[3,2-h]acridin-7-one cinnamate compounds
  申请人：Koch Michel

  公开号：US20060135545A1

  公开（公告）日：2006-06-22

  A compound selected from those of formula (I): wherein: X and Y represent a group selected from hydrogen, halogen, alkoxy, nitro, cyano, alkyl, alkenyl, polyhaloalkyl and —NR a R b wherein R a and R b are as defined in the description, Z represents oxygen or NR c wherein R c is as defined in the description, Ar represents aryl or heteroaryl, R 1 represents hydrogen or alkyl, R 2 represents a group selected from hydrogen, alkyl, —OR a and —NR a R b wherein R a and R b are as defined in the description, R 3 and R 4 represent hydrogen or alkyl, R 5 represents hydrogen, OR c , NR c R d , W 1 —C(W 2 )—U—V, W 1 —C(W 2 )—W 3 -T 1 or Z-CO—CH═CHAr wherein R c , R d , W 1 , W 2 , W 3 , U, V, T, Z and Ar are as defined in the description, its isomers, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

  从式（I）中选择的一种化合物： 其中： X和Y代表从氢、卤素、烷氧基、硝基、氰基、烷基、烯基、多卤代烷基和-NR a R b 中选择的基团， 其中R a 和R b 如描述中所定义， Z代表氧或NR c 其中R c 如描述中所定义，Ar代表芳基或杂环芳基， R 1 代表氢或烷基， R 2 代表从氢、烷基、-OR a 和-NR a R b 中选择的基团，其中R a 和R b 如描述中所定义， R 3 和R 4 代表氢或烷基， R 5 代表氢、OR c 、NR c R d 、W 1 -C(W 2 )-U-V、W 1 -C(W 2 )-W 3 -T 1 或Z-CO-CH═CHAr其中R c 、R d 、W 1 、W 2 、W 3 、U、V、T、Z和Ar如描述中所定义，其异构体，以及其与药学上可接受的酸或碱形成的加合盐，以及含有这种化合物的用于治疗癌症的药物。