N¹-[4-(4-Isocyanatobenzyl)phenyl]acetamide | 264285-83-8

• 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: N¹-[4-(4-Isocyanatobenzyl)phenyl]acetamide
• 英文别名: N-[4-(4-isocyanatobenzyl)phenyl]acetamide；N-[4-[(4-isocyanatophenyl)methyl]phenyl]acetamide
• CAS: 264285-83-8
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: ILHDSDZFKSYBMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 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：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N¹-[4-(4-Isocyanatobenzyl)phenyl]acetamide 在 pig liver esterase 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 aq. phosphate buffer 、 水 为溶剂， 反应 26.0h， 生成 N-([4-(4-aminobenzyl)phenyl]carbamoyl)-glutamic acid
  参考文献：
  名称：

  合成方法获得4,4'-亚甲基二苯基二异氰酸酯的氨基酸加合物

  摘要：

  4,4'-亚甲基二苯基二异氰酸酯（MDI）是化学工业中最重要的异氰酸酯。暴露于MDI后，肺部过敏和哮喘是主要的损害类型。MDI的白蛋白加合物可能与致敏反应的病因有关。因此，必须有敏感的和特定的生物标记物，例如血液蛋白加合物，以监测暴露于异氰酸酯的人。为了发现体内存在的血液蛋白与新的异氰酸酯加合物，需要新的合成标准品。为此，我们开发了五种方法来获得MDI的氨基酸加合物。我们合成并分离了天冬氨酸，谷氨酸，半胱氨酸和缬氨酸的MDI加合物。新的加合物通过LC-MS / MS和NMR进行表征。我们合成了相应的同位素标记的MDI加合物，以开发使用LC-MS / MS的分析方法。异氰酸酯的谷胱甘肽加合物是将反应性异氰酸酯转移到远离原始暴露部位的较远部位的一种重要方式。因此，我们使用了MDI的N-乙酰基-半胱氨酸加成物：N-乙酰基-S [[[4-（4-氨基苄基）苯基]氨基甲酰基]-半胱氨酸（MDI-AcCys）和N-乙酰基-S

  DOI：

  10.1021/tx300347e
• 作为产物：
  描述：

  N-acetyl-S-[[4-(4-acetylaminobenzyl)phenyl]carbamoyl]-cysteine 以 1,4-二氧六环 、 aq. phosphate buffer 为溶剂， 反应 29.0h， 生成 N¹-[4-(4-Isocyanatobenzyl)phenyl]acetamide
  参考文献：
  名称：

  合成方法获得4,4'-亚甲基二苯基二异氰酸酯的氨基酸加合物

  摘要：

  4,4'-亚甲基二苯基二异氰酸酯（MDI）是化学工业中最重要的异氰酸酯。暴露于MDI后，肺部过敏和哮喘是主要的损害类型。MDI的白蛋白加合物可能与致敏反应的病因有关。因此，必须有敏感的和特定的生物标记物，例如血液蛋白加合物，以监测暴露于异氰酸酯的人。为了发现体内存在的血液蛋白与新的异氰酸酯加合物，需要新的合成标准品。为此，我们开发了五种方法来获得MDI的氨基酸加合物。我们合成并分离了天冬氨酸，谷氨酸，半胱氨酸和缬氨酸的MDI加合物。新的加合物通过LC-MS / MS和NMR进行表征。我们合成了相应的同位素标记的MDI加合物，以开发使用LC-MS / MS的分析方法。异氰酸酯的谷胱甘肽加合物是将反应性异氰酸酯转移到远离原始暴露部位的较远部位的一种重要方式。因此，我们使用了MDI的N-乙酰基-半胱氨酸加成物：N-乙酰基-S [[[4-（4-氨基苄基）苯基]氨基甲酰基]-半胱氨酸（MDI-AcCys）和N-乙酰基-S

  DOI：

  10.1021/tx300347e

文献信息

• Isocyanate-Specific Hemoglobin Adduct in Rats Exposed to 4,4‘-Methylenediphenyl Diisocyanate
  作者：Gabriele Sabbioni、Renate Hartley、Dietrich Henschler、Andreas Höllrigl-Rosta、Robert Koeber、Siegfried Schneider

  DOI：10.1021/tx990096e

  日期：2000.2.1

  4'-methylenedianiline (MDA). This work presents a procedure for quantitating isocyanate-specific hemoglobin adducts. Blood proteins are used as markers of exposure and possibly as markers of dose size for the modifications of macromolecules in the target organs where the disease develops. For the quantitation of hemoglobin adducts, N(1)-[4-(4-isocyanatobenzyl)phenyl]acetamide (AcMDI) was reacted with the

  4,4'-亚甲基二苯基二异氰酸酯（MDI）是用作化学工业中间体的最重要的异氰酸酯。暴露于低水平的MDI后引起的主要损害类型是肺致敏和哮喘。MDI的蛋白质加合物可能与致敏反应的病因有关。因此，有必要采用敏感而具体的方法来监测工人的异氰酸酯暴露量。迄今为止，尿代谢产物或蛋白质加合物已被用作暴露于MDI的工人的生物标志物。但是，使用这些方法无法确定生物标记物是由于暴露于MDI还是母体芳族胺4,4'-亚甲基二苯胺（MDA）而产生的。这项工作提出了定量异氰酸酯特异性血红蛋白加合物的程序。血液蛋白被用作暴露的标志物，并可能被用作疾病发展目标器官中大分子修饰的剂量大小标志物。为了定量血红蛋白加合物，使N（1）-[4-（4-异氰酸根合苄基）苯基]乙酰胺（AcMDI）与三肽戊基-甘氨酰-甘氨酸和缬氨酸反应生成N- [4-（4-乙酰氨基苄基）苯基]氨基甲酰基]戊基-甘氨酰-甘氨酸和N- [4- [4-（乙酰氨
• End-functionalized polymers
  申请人：Kou Huiguang

  公开号：US10316114B2

  公开（公告）日：2019-06-11

  This invention relates to end-functionalized living polymers or copolymers having a structure represented by the general formula 1 or 2, wherein R1 is a hydrogen atom, a methyl group, or a radically non-polymerizable organic group containing 1 to 20 carbon atoms. R2 is a functional end group of a vinyl hetero monomer selected from the group consisting of hydroxy, epoxy, silyl, NH2, NH(C1-C6alkyl), N(C1-C6alkyl)2, —CH═CH2, —C≡CH, —C(CH3)═CH2, —O—CH═CH2, (—O—CH2—CH2)1-10—OH, —OR20, —COOR20, —CONHR20, —OCONHR20, —OCOR20 and —NH—CO—R20, wherein R20 is linear or branched C1-C20 alkyl or linear or branched C1-C20 alkyl substituted with hydroxy, epoxy, silyl, NH2 or N(C1-C6alkyl)2; or R20 is phenyl, benzyl, —CH═CH2, —C≡CH or —C(CH3)═CH2, or R2 is a residue of an acrylic acid (CH2═CH—COO—*), methacrylic acid, (CH2═C(CH3)—COO—*) or CH(CH3)═CH—COO—* or R2 is a residue of a dicarboxylic acid HOOC—Rc—COO—* or C1-C6alkyl-OOC—Rc—COO—* wherein Rc is C1-C20 alkylene, C1-C20alkenylene or phenylene; or R2 is a residue derived from the reaction of an isocyanate Ra—NCO with the hydroxy group or with the amine group of the vinyl hetero monomer, said residue being Ra—NHCOO—* or Ra—NHCO—NH—* wherein Ra is unsubstituted C1-C20alkyl, C1-C20cycloalkyl or C1-C20alkyl substituted with hydroxy, epoxy, silyl, NH2, NH(C1-C6alkyl) or N(C1-C6alkyl)2; or R2 is a residue derived from the reaction of a diisocyanate residue OCN—Rb—NCO with the hydroxy group or with the amine group of the vinyl hetero monomer, said residue being *—OOC—NH—Rb—NCO or *—HNOC—NH—Rb—NCO or *—OOC—NH—Rb—NHCOR30 wherein Rb is C1-C20 alkylene or C1-C20cycloalkylene or phenylene and R30 is a residue of hydroxyethylacrylate (CH2═CH—COO—(CH2)2—O*), hydroxyethylmethacrylate (CH2═C(CH3)—COO—(CH2)2—O*), hydroxybutylacrylate (CH2═CH—COO—(CH2)4—O*) or hydroxybutylmethacrylate (CH2═C(CH3)—COO—(CH2)4—O*), A is the hetero atom of the vinyl hetero monomer selected from the group consisting of oxygen, nitrogen, sulfur and silicon; and if R2 is silyl and M is a direct bond, A is a direct bond; M is a bond or a divalent group linking the heteroatom of the vinyl hetero monomer and the functional end group of the vinyl hetero monomer said M being selected from the group consisting of C1-50 alkylene, C1-50 (hetero)alkylene, arylene and heteroarylene; X is a halogen atom, a nitroxide group or a sulphide group, Zn is a polymer or copolymer segment of random-, gradient- or block-type structure, which is built up from vinylic monomers selected from the group consisting of isoprene, 1,3-butadiene, α-C5-18alkene, 4-vinyl-pyridine, 2-vinyl-pyridine, vinyl-imidazole, N-vinylpyrrolidone, dimethylacrylamide, 3-dimethylamino-propylmethacrylamide, styrene, substituted styrene and a compound of formula CH2═C(R3)—C(═R4)—R5, wherein R3 is a hydrogen atom or a methyl group, R4 is oxygen atom or sulfur atom; R5 is NH2, hydroxy, unsubstituted C1-18 alkoxy, C2-100alkoxy interrupted by at least one N and/or O atom, hydroxy-substituted C1-18alkoxy, unsubstituted C1-18alkylamino, di(C1-18alkyl)amino, hydroxy-substituted C1-18alkylamino, hydroxy-substituted di(C1-18alkyl)amino or —O—CH2—CH2—N(CH3)2; Y is the chain terminus of the polymer/copolymer Zn and Y represents the fragment of a polymerization initiator capable of initiating polymerization; Y1 represents a di-, tri- or polyvalent fragment of a di-, tri-, or polyfunctional NMP initiator; m is 2, 3 or 4, preferably 2; n is the number of monomer units Z and is between 10 and 5000.

  本发明涉及具有通式 1 或 2 所代表结构的末端官能化活聚合物或共聚物，其中 R1 是氢原子、甲基或含有 1 至 20 个碳原子的非聚合有机基团。R2 是乙烯基杂单体的官能末端基团，选自羟基、环氧基、硅烷基、NH2、NH(C1-C6 烷基)、N(C1-C6 烷基)2、-CH═CH2、-C≡CH、-C(CH3)═CH2、-O-CH═CH2、(-O-CH2-CH2)1-10-OH-OR20、-COOR20、-CONHR20、-OCONHR20、-OCOR20 和-NH-CO-R20，其中 R20 是直链或支链 C1-C20 烷基或被羟基、环氧基、硅烷基、NH2 或 N（C1-C6 烷基）2 取代的直链或支链 C1-C20 烷基；或 R20 是苯基、苄基、-CH═CH2、-C≡CH 或 -C(CH3)═CH2，或 R2 是丙烯酸 (CH2═CH-COO-*)、甲基丙烯酸的残基、(CH2═C(CH3)-COO-*) 或 CH(CH3)═CH-COO-* 或 R2 是二羧酸 HOOC-Rc-COO-* 或 C1-C6 烷基-OOC-Rc-COO-*的残留物，其中 Rc 是 C1-C20 亚烷基、C1-C20 亚烯基或亚苯基；或 R2 是异氰酸酯 Ra-NCO 与乙烯基杂单体的羟基或胺基反应生成的残留物，所述残留物为 Ra-NHCOO-* 或 Ra-NHCO-NH-*，其中 Ra 是未取代的 C1-C20 烷基、C1-C20 环烷基或被羟基、环氧基、硅烷基、NH2、NH(C1-C6 烷基)或 N(C1-C6烷基)2取代的 C1-C20 烷基；或 R2 是二异氰酸酯残基 OCN-Rb-NCO 与乙烯基杂单体的羟基或胺基反应生成的残基、所述残基为 *-OOC-NH-Rb-NCO 或 *-HNOC-NH-Rb-NCO 或 *-OOC-NH-Rb-NHCOR30，其中 Rb 为 C1-C20 亚烷基或 C1-C20 环亚烷基或亚苯基，R30 为羟乙基丙烯酸酯（CH2═CH-COO-(CH2)2-O*）的残基、羟乙基甲基丙烯酸酯（CH2═C(CH3)-COO-(CH2)2-O*）、羟丁基丙烯酸酯（CH2═CH-COO-(CH2)4-O*）或羟丁基甲基丙烯酸酯（CH2═C(CH3)-COO-(CH2)4-O*）的残基，A 是乙烯基杂单体的杂原子，选自由氧、氮、硫和硅组成的组；如果 R2 是硅烷基且 M 是直接键，则 A 是直接键；M 是连接乙烯基杂单体的杂原子和乙烯基杂单体的官能团的键或二价基团，所述 M 选自 C1-50 亚烷基、C1-50（杂）亚烷基、芳基和杂芳基组成的组；Zn 是无规、梯度或块状结构的聚合物或共聚物片段，由选自异戊二烯、1,3-丁二烯、 α-C5-18烯、4-乙烯基吡啶2-乙烯基吡啶、乙烯基咪唑、N-乙烯基吡咯烷酮、二甲基丙烯酰胺、3-二甲基氨基丙基甲基丙烯酰胺、苯乙烯、取代苯乙烯和式 CH2═C(R3)-C(═R4)-R5 的化合物，其中 R3 是氢原子或甲基，R4 是氧原子或硫原子；R5 是 NH2、羟基、未取代的 C1-18 烷氧基、被至少一个 N 原子和/或 O 原子打断的 C2-100 烷氧基、羟基取代的 C1-18 烷氧基、未取代的 C1-18 烷基氨基、二(C1-18 烷基)氨基、羟基取代的 C1-18 烷基氨基、羟基取代的二(C1-18 烷基)氨基或 -O-CH2-CH2-N(CH3)2；Y 是聚合物/共聚物 Zn 的链终端，Y 代表能引发聚合的聚合引发剂的片段；Y1 代表二价、三价或多价 NMP 引发剂的片段；m 是 2、3 或 4，最好是 2；n 是单体单元 Z 的数目，介于 10 和 5000 之间。
• Peroxidic Perflouropolyethers
  申请人：MARCHIONNI Giuseppe

  公开号：US20080194881A1

  公开（公告）日：2008-08-14

  Peroxidic perfluoropolyethers having formula: X 1 —O(CF 2 O) n1 (CF 2 CF 2 O) m1 (CF 2 (CF 2 ) z CF 2 O) p1 (O) h —X 2 (I) wherein: X 1 and X 2 , equal to or different from each other, are chain end groups selected among —CF 2 COF, —COF, —SO 2 F; n1, m1, p1 and h are integers such that the number average molecular weight is in the range 700-100,000; z=1 or 2; with the proviso that: the m1/n1 ratio is between 0.2 and 10; the p1/(n1+m1) ratio is lower than 0.05; the h/(n1+m1+p1) ratio is such that the PO content, defined as grams of active oxygen/100 g of compound, is in the range 0.8-4.5, preferably 1.4-3.8; the perfluorooxyalkylene units being statistically distributed along the polymeric chain.
• ISOCYANATO TERMINATED PRECURSOR AND METHOD OF MAKING THE SAME
  申请人：JONES THOMAS N.

  公开号：US20090054604A1

  公开（公告）日：2009-02-26

  A method of making an isocyanato terminated precursor for polyurethane is disclosed. The method comprises heating an isocyanate containing about two or more isocyanato groups per molecule at a temperature of up to 80 degrees Celsius and at a pressure of about 1 atmosphere. The method further comprises mixing a modified vegetable oil comprising about two or more hydroxyl groups per molecule with the isocyanate at a molar equivalent ratio of at least 2:1 isocyanate to vegetable oil for a predetermined time period to form the isocyanato terminated precursor.
• Additives for Halopolymers
  申请人：Abusleme Julio A.

  公开号：US20090326154A1

  公开（公告）日：2009-12-31

  Polymeric compositions comprising: 1) at least one thermoprocessable semicrystalline halo-polymer; 2) an additive in amounts between 0.01 and 10% by weight of 1) one or more (per)fluoropolyether polymers of formula: Q-O-[A-B] z -[A-B′] z′ -A-Q′ (I) wherein: A=—(X) a —O-A′-(X′) b — wherein A′ is a perfluoropolyether chain; X, X′=—CF 2 —, —CF 2 CF 2 —, —CF(CF 3 )—; a, b=0 or 1; B derives from one or more olefins, of which at least one homopolymerizable by radical way, of formula: —[(CR 1 R 2 —CR 3 R 4 ) j (CR 5 R 6 —CR 7 R 8 ) j′ ]— (Ia) wherein j=1-30, j′=0-29, with the proviso that 2<(j+j′)<30; R 1 -R 8 =halogen, H, C 1 -C 6 (per)haloalkyl, C 1 -C 6 alkyl, or C 1 -C 6 oxy(per)fluoroalkyl; B′=(Ia) but at least one of R 1 -R 8 has a meaning different from that in B, and 2≦(j+j′)<30; z≧2; z′ is 0 or an integer; z, z′ are such that the number average molecular weight of (I) is between 500 and 500,000; Q, Q′=C 1 -C 3 perfluoroalkyl; C 1 -C 6 alkyl; or functional end group(s).