6-(4-硝基苯氧基)己酸甲酯 | 106275-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-(4-硝基苯氧基)己酸甲酯
• 英文名称: methyl 6-(4-nitrophenoxy)hexanoate
• 英文别名: 6-(4-Nitrophenoxy)-hexanoic acid methyl ester
• CAS: 106275-33-6
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: CVEFTEADWHWATB-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  392.3±22.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-硝基苯氧基)己酸甲酯 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 49.67h， 生成 6-<4-phenoxy>hexanoic acid
  参考文献：
  名称：

  DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard

  摘要：

  A series of DNA-targeted aniline mustards have been prepared, and their chemical reactivity and in vitro and in vivo cytotoxicity have been evaluated and compared with that of the corresponding simple aniline mustards. The alkylating groups were anchored to the DNA-intercalating 9-aminoacridine chromophore by an alkyl chain of fixed length attached at the mustard 4-position through a link group X, while the corresponding simple mustards possessed an electronically identical small group at this position. The link group was varied to provide a series of compounds of similar geometry but widely differing mustard reactivity. Variation in biological activity should then largely be a consequence of this varying reactivity. Rates of mustard hydrolysis in the two series related only to the electronic properties of the link group, with attachment of the intercalating chromophore having no effect. The cytotoxicities of the simple mustards correlated well with group electronic properties (with a 200-300-fold range in IC50S). The corresponding DNA-targeted mustards were much more potent (up to 100-fold), but their IC50 values varied much less with linker group electronic properties. Most of the DNA-targeted mustards showed in vivo antitumor activity, being both more active and more dose-potent than either the corresponding untargeted mustards and chlorambucil. These results show that targeting alkylating agents to DNA by attachment to DNA-affinic units may be a useful strategy.

  DOI：

  10.1021/jm00166a015
• 作为产物：
  描述：

  1-((5-bromopentyl)oxy)-4-nitrobenzene 在 盐酸 、 potassium cyanide 、 乙醇 作用下， 生成 6-(4-硝基苯氧基)己酸甲酯
  参考文献：
  名称：

  Ashley et al., Journal of the Chemical Society, 1959, p. 897,901

  摘要：

  DOI：
• 作为试剂：
  描述：

  对硝基苯酚 、 potassium carbonate 、 碘化钠 、 6-溴己酸甲酯 在 丙酮 、 水 、 6-(4-硝基苯氧基)己酸甲酯 、 乙酸乙酯 、 正己烷 、 84 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以to obtain pure 6-(4-nitrophenoxy)-hexanoic acid methyl ester (130 g) as a white powder with a melting point of 84的产率得到6-(4-硝基苯氧基)己酸甲酯
  参考文献：
  名称：

  Absorbable polyurethanes and methods of use thereof

  摘要：

  本发明涉及一种新颖的生物可吸收和生物可降解单体化合物，由此制得的生物可吸收和生物可降解聚合物，以及制备这种单体和聚合物的方法。这些单体和聚合物在制药递送系统、组织工程应用、组织粘合剂产品、可植入医疗器械、泡沫和网状泡沫用于伤口愈合和药物递送、骨止血剂和骨空隙填充剂、粘附防止屏障、网格、过滤器、支架、医疗器械涂层、制药药物配方、消费品和化妆品和制药包装、服装、输液装置、血液采集管和装置、其他医疗管道、皮肤护理产品和经皮递药材料中有用。

  公开号：

  US08901347B1

文献信息

• Functionalized drugs and polymers derived therefrom
  申请人：Bezwada S. Rao

  公开号：US20060172983A1

  公开（公告）日：2006-08-03

  Compounds selected from: where DRUG-OH, DRUG-COOH and DRUG-NH 2 are biologically active compounds; each X is independently selected from —CH 2 COO— (glycolic acid moiety), —CH(CH 3 )COO— (lactic acid moiety), —CH 2 CH 2 OCH 2 COO— (dioxanone moiety), —CH 2 CH 2 CH 2 CH 2 CH 2 COO— (caprolactone moiety), —(CH 2 ) y COO—, where y is 2-4 or 6-24 and —(CH 2 CH 2 O) z CH 2 COO—, where z is 2-24; each Y is independently selected from —COCH 2 O— (glycolic ester moiety), —COCH(CH 3 )O— (lactic ester moiety), —COCH 2 OCH 2 CH 2 O— (dioxanone ester moiety), —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester moiety), —CO(CH 2 ) m O—, where m is 2-4 or 6-24 and —COCH 2 O(CH 2 CH 2 O) n — where n is between 2-24; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; and p is 1-6. Multi-functional compounds and drug dimers, oligomers and polymers are also disclosed.

  从中选择的化合物：其中DRUG-OH，DRUG-COOH和DRUG-NH2是生物活性化合物；每个X独立地从—CH2COO—（乙二酸基团），—CH(CH3)COO—（乳酸基团），—CH2CH2OCH2COO—（二氧杂环己酮基团），—CH2CH2CH2CH2CH2COO—（己内酯基团），—(CH2)yCOO—中选择，其中y为2-4或6-24和—(CH2CH2O)zCH2COO—，其中z为2-24；每个Y独立地从—COCH2O—（乙二酸酯基团），—COCH(CH3)O—（乳酸酯基团），—COCH2OCH2CH2O—（二氧杂环己酮酯基团），—COCH2CH2CH2CH2CH2O—（己内酯酯基团），—CO(CH2)mO—，其中m为2-4或6-24和—COCH2O(CH2CH2O)n—，其中n为2-24；R′为氢，苄基或烷基，烷基可以是直链或支链；p为1-6。还披露了多功能化合物和药物二聚体、寡聚体和聚合物。
• Bioabsorbable and biocompatible polyurethanes and polyamides for medical devices
  申请人：S. Bezwada Rao

  公开号：US20060188547A1

  公开（公告）日：2006-08-24

  Absorbable polyurethanes, polyamides and polyester urethanes prepared from at least one compound selected from: or the diamines and diisocyanates thereof, wherein each X represents a member independently selected from —CH 2 COO— (glycolic acid moiety), —CH(CH 3 )COO— (lactic acid moiety), —CH 2 CH 2 OCH 2 COO— (dioxanone), —CH 2 CH 2 CH 2 CH 2 CH 2 COO— (caprolactone moiety), —(CH 2 ) y COO— where y is one of the numbers 2, 3, 4 or 6-24 inclusive, and —(CH 2 CH 2 O) z′ CH 2 COO— where z′ is an integer between 2 and 24, inclusive; each Y represents a member independently selected from —COCH 2 O— (glycolic ester moiety), —COCH(CH 3 )O— (lactic ester moiety), —COCH 2 OCH 2 CH 2 O— (dioxanone ester), —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester), —CO(CH 2 ) m O— where m is an integer between 2, 3, 4 or 6-24 inclusive, —COCH 2 O(CH 2 CH 2 O) n — where n is an integer between 2 and 24, inclusive; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; p is an integer between 1 and 4, inclusive; and Rn represents one or more members selected from H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO 2 , which is attached directly to an aromatic ring or attached through an aliphatic chain. Absorbable polymers prepared from these compounds are useful for drug delivery, tissue engineering, tissue adhesives, adhesion prevention and other implantable medical devices.

  由至少选择自以下化合物制备的可吸收聚氨酯、聚酰胺和聚酯聚氨酯：或其二胺和二异氰酸酯，其中每个X分别代表从—CH2COO—（乙二醇酸基团），—CH（CH3）COO—（乳酸酸基团），—CH2CH2OCH2COO—（二氧环己酮），—CH2CH2CH2CH2CH2COO—（己内酯基团），—（CH2）yCOO—其中y是2、3、4或6-24之间的一个数字，以及—（CH2CH2O）z′CH2COO—其中z′是介于2和24之间的整数；每个Y分别代表从—COCH2O—（乙二醇酸酯基团），—COCH（CH3）O—（乳酸酸酯基团），—COCH2OCH2CH2O—（二氧环己酮酯基团），—COCH2CH2CH2CH2CH2O—（己内酯酯基团），—CO（CH2）mO—其中m是介于2、3、4或6-24之间的整数，—COCH2O（CH2CH2O）n—其中n是介于2和24之间的整数；R′是氢、苄基或烷基，烷基可以是直链或支链；p是介于1和4之间的整数；Rn代表选择自H、烷氧基、苯甲氧基、醛、卤素、羧酸和—NO2的一个或多个成员，它直接附着在芳香环上或通过脂肪链附着。从这些化合物制备的可吸收聚合物对于药物传递、组织工程、组织粘接、粘着预防和其他可植入医疗器械非常有用。
• BIOABSORBABLE AND BIOCOMPATIBLE POLYURETHANES AND POLYAMIDES FOR MEDICAL DEVICES
  申请人：Bezwada Rao S.

  公开号：US20120158127A1

  公开（公告）日：2012-06-21

  Absorbable polyurethanes, polyamides and polyester urethanes prepared from at least one compound selected from: or the corresponding diamines or diisocyanates thereof, wherein each X independently represents —CH 2 COO—, —CH(CH 3 )COO—, —CH 2 CH 2 OCH 2 COO—, —CH 2 CH 2 CH 2 CH 2 CH 2 COO—, —(CH 2 ) y COO— where y is 2 to 4 or 6 to 24, or —(CH 2 CH 2 O) z′ CH 2 COO— where z′ is 2 to 24; each Y represents —COCH 2 O—, —COCH(CH 3 )O—, —COCH 2 OCH 2 CH 2 O—, —COCH 2 CH 2 CH 2 CH 2 CH 2 O—, —CO(CH 2 ) m O— where m is 2 to 4 or 6 to 24, or —COCH 2 O(CH 2 CH 2 O) n — where n is 2 to 24; R′ is hydrogen, benzyl or straight-chained or branched alkyl; p is 1 to 4; and Rn represents one or more members selected from H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid and —NO 2 , which is attached directly to an aromatic ring or attached through an aliphatic chain. Absorbable polymers prepared from these compounds are useful for drug delivery, tissue engineering, tissue adhesives, adhesion prevention and other implantable medical devices.

  可吸收的聚氨酯、聚酰胺和聚酯尿素是由至少一种选择自以下化合物或其相应的二胺或二异氰酸酯制备而成：其中每个X独立地表示-CH2COO-、-CH(CH3)COO-、-CH2CH2OCH2COO-、-CH2CH2CH2CH2CH2COO-、-(CH2)yCOO-，其中y为2至4或6至24，或-(CH2CH2O)z'CH2COO-，其中z'为2至24；每个Y表示-COCH2O-、-COCH(CH3)O-、-COCH2OCH2CH2O-、-COCH2CH2CH2CH2CH2O-、-CO(CH2)mO-，其中m为2至4或6至24，或-COCH2O(CH2CH2O)n-，其中n为2至24；R'为氢、苄基或直链或支链烷基；p为1至4；Rn表示选择自H、烷氧基、苄氧基、醛、卤素、羧酸和-NO2的一个或多个成员，它直接附着在芳香环上或通过脂肪链附着。从这些化合物制备的可吸收聚合物可用于药物输送、组织工程、组织粘合剂、粘着预防和其他可植入医疗器械。
• FUNCTIONALIZED DRUGS AND POLYMERS THEREFROM
  申请人：Bezwada Rao S.

  公开号：US20100152272A1

  公开（公告）日：2010-06-17

  Compounds selected from: where DRUG-OH, DRUG-COOH and DRUG-NH 2 are biologically active compounds; each X is independently selected from —CH 2 COO— (glycolic acid moiety), —CH(CH 3 )COO— (lactic acid moiety), —CH 2 CH 2 OCH 2 COO— (dioxanone moiety), —CH 2 CH 2 CH 2 CH 2 CH 2 COO— (caprolactone moiety), —(CH 2 ) y COO—, where y is 2-4 or 6-24 and —(CH 2 CH 2 O) z CH 2 COO—, where z is 2-24; each Y is independently selected from —COCH 2 O— (glycolic ester moiety), —COCH(CH 3 )O— (lactic ester moiety), —COCH 2 OCH 2 CH 2 O— (dioxanone ester moiety), —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester moiety), —CO(CH 2 ) m O—, where m is 2-4 or 6-24 and —COCH 2 O(CH 2 CH 2 O) n — where n is between 2-24; R′ is hydrogen, benzyl or an alkyl group, the alkyl group being either straight-chained or branched; and p is 1-6. Multi-functional compounds and drug dimers, oligomers and polymers are also disclosed.

  所选化合物包括：DRUG-OH，DRUG-COOH和DRUG-NH2是具有生物活性的化合物；每个X独立选择自—CH2COO—（乙二酸酯基），—CH(CH3)COO—（乳酸酯基），—CH2CH2OCH2COO—（二氧杂环己酮酯基），—CH2CH2CH2CH2CH2COO—（己内酯酯基），—（CH2）yCOO—，其中y为2-4或6-24和—（CH2CH2O）zCH2COO—，其中z为2-24；每个Y独立选择自—COCH2O—（乙二酸酯基），—COCH(CH3)O—（乳酸酯基），—COCH2OCH2CH2O—（二氧杂环己酮酯基），—COCH2CH2CH2CH2CH2O—（己内酯酯基），—CO（CH2）mO—，其中m为2-4或6-24和—COCH2O（CH2CH2O）n—，其中n为2-24；R'为氢，苄基或烷基，所述烷基可以是直链或支链；p为1-6。还公开了多功能化合物和药物二聚体、寡聚体和聚合物。
• ABSORBABLE POLYURETHANES AND METHODS OF USE THEREOF
  申请人：BEZWADA BIOMEDICAL, LLC

  公开号：US20150080301A1

  公开（公告）日：2015-03-19

  Disclosed are novel bioabsorbable and biodegradable monomer compounds, bioabsorbable and biodegradable polymers therefrom, and methods of making such monomers and polymers, which are useful in pharmaceutical delivery systems, tissue engineering applications, tissue adhesives products, implantable medical devices, foams and reticulated foams for wound healing and drug delivery, bone hemostats and bone void fillers, adhesion prevention barriers, meshes, filters, stents, medical device coatings, pharmaceutical drug formulations, consumer product and cosmetic and pharmaceutical packaging, apparel, infusion devices, blood collection tubes and devices, other medical tubes, skin care products, and transdermal drug delivery materials.

  本发明公开了一种新型的可生物吸收和可生物降解的单体化合物，以及由此制得的可生物吸收和可生物降解的聚合物，以及制备这些单体和聚合物的方法。这些单体和聚合物可用于制造药物输送系统、组织工程应用、组织粘合产品、可植入医疗器械、用于伤口愈合和药物输送的泡沫和网状泡沫、骨止血剂和骨空隙填充剂、粘附预防屏障、网格、过滤器、支架、医疗器械涂层、制药药物配方、消费品、化妆品和制药包装、服装、输液器、采血管和设备、其他医疗管道、皮肤护理产品和经皮药物输送材料。