4-chloro-3-nitro-cinnamic acid | 20797-48-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 4-chloro-3-nitro-cinnamic acid
• 英文别名: β-(4-Chlor-3-nitro-phenyl)-acrylsaeure；4-Chlor-3-nitro-zimtsaeure；4-chloro-3-nitrocinnamic acid；p-Chlor-m-nitro-zimtsaeure；3-Nitro-4-chlorzimtsaeure；3-(4-Chloro-3-nitrophenyl)prop-2-enoic acid
• CAS: 20797-48-2
• 化学式: C₉H₆ClNO₄
• mdl: MFCD00063311
• 分子量: 227.604
• InChiKey: QBDALTIMHOITIU-UHFFFAOYSA-N

物化性质

• 熔点：
  188-190 °C(lit.)
• 沸点：
  408.6±35.0 °C(Predicted)
• 密度：
  1.4751 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2916399090
• 危险品运输编号：
  NONH for all modes of transport

制备方法与用途

应用

4-氯-3-硝基肉桂酸可作为有机合成中间体及医药中间体，在实验室研发和化工、制药过程中广泛应用。

制备

在250 mL干燥三颈烧瓶中，加入一定物质的量比的新蒸4-氯-3-硝基苯甲醛与醋酸酐，并添加适量催化剂。振荡混合均匀后，安装温度计和冷凝管（上端接氯化钙干燥管），在设定温度下进行磁力搅拌并充分反应一段时间。反应结束后，用饱和Na2CO3溶液调节pH至弱碱性。随后用水蒸汽蒸馏直至无油珠状液体为止，再使用少量活性炭吸附杂质，得到无色液体。趁热抽滤后，用盐酸调pH至3～4，此时会有大量白色晶体析出。静置一段时间后抽滤，并用少量水洗涤结晶，干燥以获得粗产品4-氯-3-硝基肉桂酸。最后，将粗产品溶于水和乙醇混合液（体积比为3∶1）中进行重结晶，即可得到黄色晶体的4-氯-3-硝基肉桂酸。

反应信息

• 作为反应物：
  描述：

  4-chloro-3-nitro-cinnamic acid 在 硝酸 作用下， 生成 4-chloro-3,β-dinitro-styrene
  参考文献：
  名称：

  Functional hyperandrogenism detected by corticotropin and GnRH-analogue stimulation tests in women affected by apparently idiopathic hirsutism

  摘要：

  The etiologic diagnosis of hirsutism is often difficult. Previous studies have reported normal basal androgen and SHBG concentrations in 33-50% of hirsute women, suggesting the presence of an "idiopathic" form of hirsutism as the most frequent cause of this problem. The recent use of GnRH-analogues together with the corticotropin stimulation test allows better understanding of whether the cause of hirsutism is androgen excess and, if so, whether the origin of the latter is ovarian, adrenal or both. The present study evaluated adrenal and ovarian function in 48 young hirsute women as well as in 78 normal women matched for body mass index and age, who acted as control group. To determine ovarian function, a single 100-mug dose of GnRH analogue triptorelin was injected sc; thereafter, gonadotropins, 17-hydroxyprogesterone (17-OHP), Delta4-androstenedione (Delta4), total testosterone (T) and estradiol were determined. To better understand the adrenal function, 250 mug of 1,24 ACTH were administrated as iv infusion for 5 h, and plasma cortisol (F), 17-OHP, Delta4, DHEAS, T, 11-desossicortisol were measured. The combined use of these two stimulation tests was able to detect mild to moderate abnormalities in the steroidogenesis of ovaries alone (23%), adrenals alone (16.6%), or both (35.4%) in most hirsute women (75%) with otherwise normal baseline androgen concentrations. In particular, patients showed significantly increased responses of 17-OHP, Delta4, total T, 11-desossicortisol, and F to 1,24-ACTH administration. Moreover, they also had significantly higher 17-OHP and T responses to triptorelin. In conclusion, milder forms of functional ovarian and/or adrenal hyperandrogenism, similar to those found in clearly hyperandrogenic women, were observed and could be an underlying mechanism of idiopathic hirsutism. (J. Endocrinol. Invest. 24: 491-498, 2001) (C) 2001, Editrice Kurtis.

  DOI：

  10.1007/bf03343881
• 作为产物：
  描述：

  4-氯-3-硝基苯甲醇 在 sodium hydroxide 、 硫酸 作用下， 生成 4-chloro-3-nitro-cinnamic acid
  参考文献：
  名称：

  合成三氯乙烯和三氯乙烯

  摘要：

  DOI：

  10.1016/s0040-4039(00)89878-0

文献信息

• Cell adhesion-inhibiting antiinflammatory and immune-suppressive compounds
  申请人：Abbott Laboratories

  公开号：US20040116518A1

  公开（公告）日：2004-06-17

  The present invention relates to novel cinnamide compounds that are useful for treating inflammatory and immune diseases and cerebral vasospasm, to pharmaceutical compositions containing these compounds, and to methods of inhibiting inflammation or suppressing immune response in a mammal.

  本发明涉及新型肉桂酰胺化合物，用于治疗炎症和免疫性疾病以及脑血管痉挛，以及含有这些化合物的药物组合物，以及在哺乳动物中抑制炎症或抑制免疫反应的方法。
• [EN] VIRAL POLYMERASE INHIBITORS<br/>[FR] INHIBITEURS DE POLYMERASE VIRALE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2004065367A1

  公开（公告）日：2004-08-05

  An isomer, enantiomer, diastereoisomer or tautomer of a compound, represented by formula (I): wherein wherein A, B, R2, R3, L, M1, M2, M3, M4, Y1, Y0, Z and Sp are as defined in claim 1, or a salt thereof, as an inhibitor of HCV NS5B polymerase.

  化合物的异构体、对映体、非对映异构体或互变异构体，由式(I)所代表：其中A、B、R2、R3、L、M1、M2、M3、M4、Y1、Y0、Z和Sp如权利要求1中定义，或其盐，作为HCV NS5B聚合酶的抑制剂。
• Synthesis and characterization of two novel biological-based nano organo solid acids with urea moiety and their catalytic applications in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), coumarin-3-carboxylic acid and cinnamic acid derivatives under mild and green conditions
  作者：Mohammad Ali Zolfigol、Roya Ayazi-Nasrabadi、Saeed Baghery

  DOI：10.1039/c5ra14001c

  日期：——

  Green and straight-forward syntheses of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives using nano structure organocatalysts, namely 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid, have been developed.

  利用纳米结构有机催化剂，即2-氨基甲酰肼-1-磺酸和氨基甲酰磺酸，直接绿色合成4,4′-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的方法已经被开发出来。

• RHO KINASE INHIBITORS
  申请人：Bosanac Todd

  公开号：US20080161297A1

  公开（公告）日：2008-07-03

  Disclosed are novel substituted 2H-isoquinolin-1-one and 3H-quinazolin-4-one derivatives useful as inhibitors of Rho kinase and for treating a variety of diseases and disorders that are mediated or sustained through the activity of Rho kinase, including cardiovascular diseases, pharmaceutical compositions comprising such compounds, methods for using such compounds and processes for making such compounds.

  揭示了一种新颖的取代的2H-异喹啉-1-酮和3H-喹唑啉-4-酮衍生物，可用作Rho激酶的抑制剂，用于治疗通过Rho激酶活性介导或维持的各种疾病和疾病，包括心血管疾病，包含这些化合物的药物组合物，使用这些化合物的方法以及制备这些化合物的方法。
• Colorant compounds
  申请人：Banning H. Jeffrey

  公开号：US20060020141A1

  公开（公告）日：2006-01-26

  Compounds of the formula wherein M is either (1) a metal ion having a positive charge of +y wherein y is an integer which is at least 2, said metal ion being capable of forming a compound with at least two chromogen moieties, or (2) a metal-containing moiety capable of forming a compound with at least two chromogen moieties, z is an integer representing the number of chromogen moieties associated with the metal and is at least 2, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a, b, c, d, Y, and z are as defined herein, Q − is a COO − group or a SO 3 — group, A is an organic anion, and CA is either a hydrogen atom or a cation associated with all but one of the Q − groups.

  式中的化合物，其中M是一个带有正电荷+y的金属离子，其中y是至少为2的整数，该金属离子能够与至少两个色团基团形成化合物，或者M是一个含金属基团的基团，能够与至少两个色团基团形成化合物，z是表示与金属相关的色团基团数量的整数，至少为2，R1、R2、R3、R4、R5、R6、R7、a、b、c、d、Y和z的定义如上所述，Q-是一个COO-基团或SO3-基团，A是一个有机阴离子，CA是一个氢原子或与除一个Q-基团之外的所有Q-基团相关联的阳离子。