4-tert-Butyloxycarbonylamino-3-fluorophenyl isonitrile | 220913-44-0

• 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: 4-tert-Butyloxycarbonylamino-3-fluorophenyl isonitrile
• 英文别名: tert-butyl N-(2-fluoro-4-isocyanophenyl)carbamate
• CAS: 220913-44-0
• 化学式: C₁₂H₁₃FN₂O₂
• 分子量: 236.246
• InChiKey: PYYHPFRGSSTZMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-Butyloxycarbonylamino-3-fluorophenyl isonitrile 、 (S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(3-trimethylsilyl-2-propynyl)-1H-pyrano[3,4-c]-8-pyridone 在 六甲基二锡 作用下， 生成 (S)-9-Amino-4-ethyl-10-fluoro-4-hydroxy-11-trimethylsilanyl-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione 、 7-trimethylsilyl-10-amino-11-fluorocamptothecin
  参考文献：
  名称：

  7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents

  摘要：

  The synthesis and biological evaluation of about one dozen 7-silylcamptothecin derivatives are described. Most new compounds show potencies comparable to or better than camptothecin itself. The best compound, 11-fluoro-10-amino-7-trimethylsilylcamptothecin, is more than 20 times more potent than camptothecin in cell assays. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10181-0

文献信息

• [EN] CAMPTOTHECIN ANALOGS AND METHODS OF PREPARATION THEREOF<br/>[FR] ANALOGUES DE LA CAMPTOTHECINE ET PROCEDES D'ELABORATION
  申请人：UNIVERSITY OF PITTSBURGH

  公开号：WO1999009996A1

  公开（公告）日：1999-03-04

  (EN) The present invention provides generally a compound having general formula (1), wherein R1 and R2 are independently the same or different and are hydrogen, an alkyl group, an alkenyl group, a benzyl group, an alkynyl group, an alkoxyl group, an aryloxy group, an acyloxy group, a carbonyloxy group, a carbamoyloxy group, a halogen, a hydroxyl group, a nitro group, a cyano group, an azido group, a formyl group, a hydrazino group, an acyl group, an amino group, -SRc, wherein, Rc is hydrogen, an acyl group, an alkyl group, or an aryl group, or R1 and R2 together form a group of the formula -O(CH2)nO- wherein n represents the integer 1 or 2; R3 is H, F, a halogen atom, a nitro group, an amino group, a hydroxyl group, or a cyano group; or R2 and R3 together form a group of the formula -O(CH2)nO- wherein n represents the integer 1 or 2; R4 is H, F, a C1-3 alkyl group, a C2-3 alkenyl group, a C2-3 alkylnyl group, or a C1-3 alkoxyl group; R5 is a C1-10 alkyl group, or a propargyl group; and R6, R7 and R8 are independently a C1-10 alkyl group, a C2-10 alkenyl group, C2-10 alkynyl group, an aryl group or a -(CH2)NR9 group, wherein N is an integer within the range of 1 through 10 and R9 is a hydroxyl group, alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group or a nitro group; and pharmaceutically acceptable salts thereof.(FR) L'invention concerne globalement un composé de formule générale (1) et les sels pharmaceutiquement acceptables de ce composé. Dans ladite formule, R1 et R2 sont indépendamment identiques ou différents et représentent hydrogène, un groupe alkyle, un groupe alcényle, un groupe benzyle, un groupe alcynyle, un groupe alcoxyle, un groupe aryloxy, un groupe acyloxy, un groupe carbonyloxy, un groupe carbamoyloxy, un halogène, un groupe hydroxyle, un groupe nitro, un groupe cyano, un groupe azido, un groupe formyle, un groupe hydrazino, un groupe acyle, un groupe amino, -SRc, sachant que Rc est hydrogène, un groupe acyle, un groupe alkyle, ou un groupe aryle, ou bien R1 et R2 forment ensemble un groupe de formule -O(CH2)nO- où n est un entier égal à 1 ou à 2; R3 est H, F, un atome d'halogène, un groupe nitro, un groupe amino, un groupe hydroxyle, ou un groupe cyano; ou bien R2 et R3 forment ensemble un groupe de formule-O(CH2)nO- où n est un entier égal à 1 ou à 2; R4 est H, F, un groupe alkyle C1-3, un groupe alcényle C2-3, un groupe alcynyle C2-3, ou un groupe alcoxyle C1-3; R5 est un groupe alkyle C1-10, ou un groupe propargyle; et R6, R7 et R8 sont indépendamment un groupe alkyle C1-10, un groupe alcényle C2-10, un groupe alcynyle C2-10, un groupe aryle ou un groupe -(CH2)NR9 où N est un entier compris entre 1 et 10, et R9 est un groupe hydroxyle, un groupe alcoxy, un groupe amino, un groupe alkylamino, un groupe dialkylamino, un atome d'halogène, un groupe cyano ou un groupe nitro.

  本发明提供了一般式（1）的化合物，其中R1和R2分别独立相同或不同，可以是氢、烷基、烯基、苄基、炔基、烷氧基、芳氧基、酰氧基、羰基氧基、氨基甲酰氧基、卤素、羟基、硝基、氰基、叠氮基、甲酰基、肼基、酰基、氨基、-SRc，其中Rc是氢、酰基、烷基或芳基，或R1和R2共同形成公式为-O（CH2）nO-的基团，其中n表示整数1或2；R3是H、F、卤素原子、硝基、氨基、羟基或氰基；或R2和R3共同形成公式为-O（ ）nO-的基团，其中n表示整数1或2；R4是H、F、C1-3烷基、C2-3烯基、C2-3烷基基或C1-3烷氧基；R5是C1-10烷基或丙炔基；R6、R7和R8分别是C1-10烷基、C2-10烯基、C2-10炔基、芳基或-( )NR9基团，其中N是1到10的整数，R9是羟基、烷氧基、氨基、烷基氨基、二烷基氨基、卤素原子、氰基或硝基；以及其药学上可接受的盐。
• [EN] CAMPTOTHECIN ANALOGS AND METHODS OF PREPARATION THEREOF<br/>[FR] ANALOGUES DE CAMPTOTHECINE ET METHODES DE PREPARATION
  申请人：UNIV PITTSBURGH

  公开号：WO2000035924A1

  公开（公告）日：2000-06-22

  A compound and a method of synthesizing a compound having general formula (1): wherein R?1 and R2¿ are independently the same or different and are hydrogen, an alkyl group, an alkenyl group, a benzyl group, an alkynyl group, an alkoxy group, an aryloxy group, an acyloxy group, -OC(O)ORd, wherein Rd is an alkyl group, a carbamoyloxy group, a halogen, a hydroxy group, a nitro group, a cyano group, an azido group, a formyl group, a hydrazino group, an acyl group, an amino group, -SRc, wherein Rc is hydrogen, an acyl group, an alkyl group, or an aryl group, or R?1 and R2¿ together form a group of the formula -O(CH¿2?)nO- wherein n represents the integer 1 or 2; R?3¿ is H, F, a halogen atom, a nitro group, an amino group, a hydroxy group, or a cyano group; or R?2 and R3¿ together form a group of the formula -O(CH¿2?)n O- wherein n represents the integer 1 or 2; R?4¿ is H, a trialkylsilyl group, F, a C¿1-3? alkyl group, a C2-3 alkenyl group, a C2-3 alkynyl group, or a C1-3 alkoxy group; R?5¿ is a C¿1-10? alkyl group, an allyl group, a benzyl group or a propargyl group; and R?6, R7 and R8¿ are independently a C¿1-10? alkyl group, a C2-10 alkenyl group, a C2-10 alkynyl group, an aryl group or a -(CH2)NR?9¿ group, wherein N is an integer within the range of 1 through 10 and R9 is a hydroxy group, alkoxy group, an amino group, alkylamino group, a dialkylamino group, a halogen atom, a cyano group or a nitro group; and R11 is an alkylene group or an alkenylene group, and pharmaceutically acceptable salts thereof.

  一种化合物及其合成方法，其具有通式（1）： 其中R1和R2独立且相同或不同，可以是氢、烷基、烯基、苄基、炔基、烷氧基、芳氧基、酰氧基、-OC（O）ORd（其中Rd为烷基、氨基甲酰氧基、卤素、羟基、硝基、氰基、叠氮基、甲酰基、肼基、酰基、氨基、-SRc（其中Rc为氢、酰基、烷基或芳基），或R1和R2组成式为-O（CH2）nO-的基团，其中n表示整数1或2；R3为氢、氟、卤素原子、硝基、氨基、羟基或氰基；或R2和R3组成式为-O（ ）nO-的基团，其中n表示整数1或2；R4为氢、三烷基硅基、氟、C1-3烷基、C2-3烯基、C2-3炔基或C1-3烷氧基；R5为C1-10烷基、烯丙基、苄基或丙炔基；R6、R7和R8独立地为C1-10烷基、C2-10烯基、C2-10炔基、芳基或-( )NR9（其中N为1至10的整数，R9为羟基、烷氧基、氨基、烷基氨基、二烷基氨基、卤素原子、氰基或硝基）；R11为烷基或烯基，以及其药物可接受的盐。
• Camptothecin analogs and methods of preparation thereof
  申请人：——

  公开号：US20020193598A1

  公开（公告）日：2002-12-19

  A compound and a method of synthesizing a compound having the following general formula (1): 1 wherein R 1 and R 2 are independently the same or different and are hydrogen, an alkyl group, an alkenyl group, a benzyl group, an alkynyl group, an alkoxy group, an aryloxy group, an acyloxy group, —OC(O)OR d , wherein R d is an alkyl group, a carbamoyloxy group, a halogen, a hydroxy group, a nitro group, a cyano group, an azido group, a formyl group, a hydrazino group, an acyl group, an amino group, —SR c , wherein, R c is hydrogen, an acyl group, an alkyl group, or an aryl group, or R 1 and R 2 together form a group of the formula —O(CH 2 ) n O— wherein n represents the integer 1 or 2; R 3 is H, F, a halogen atom, a nitro group, an amino group, a hydroxy group, or a cyano group; or R 2 and R 3 together form a group of the formula —O(CH 2 ) n O— wherein n represents the integer 1 or 2; R 8 is H, a trialkylsilyl group, F, a C 1-3 alkyl group, a C 2-3 alkenyl group, a C 2-3 alkynyl group, or a C 1-3 alkoxy group; R 5 is a C 1-10 alkyl group, an allyl group, a benzyl group or a propargyl group; and R 6 , R 7 and R 8 are independently a C 1-10 alkyl group, a C 2-10 alkenyl group, a C 2-10 alkynyl group, an aryl group or a —(CH 2 ) N R 9 group, wherein N is an integer within the range of 1 through 10 and R 9 is a hydroxy group, alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group or a nitro group; and R 11 is an alkylene group or an alkenylene group, and pharmaceutically acceptable salts thereof.

  一种具有以下通式（1）的化合物及其合成方法：其中R1和R2独立地相同或不同，可以是氢、烷基、烯基、苯基、炔基、烷氧基、芳基氧基、酰氧基、—OC（O）ORd，其中Rd是烷基、氨基甲酰氧基、卤素、羟基、硝基、氰基、偶氮基、甲酰基、肼基、酰基、氨基、—SRc，其中，Rc是氢、酰基、烷基或芳基，或R1和R2共同形成式为—O（CH2）nO—的基团，其中n表示整数1或2；R3是H、F、卤素原子、硝基、氨基、羟基或氰基；或R2和R3共同形成式为—O（ ）nO—的基团，其中n表示整数1或2；R8是H、三烷基硅基、F、C1-3烷基、C2-3烯基、C2-3炔基或C1-3烷氧基；R5是C1-10烷基、烯丙基、苯甲基或丙炔基；R6、R7和R8独立地是C1-10烷基、C2-10烯基、C2-10炔基、芳基或—（ ）NR9基团，其中N在1至10范围内是整数，R9是羟基、烷氧基、氨基、烷基氨基、二烷基氨基、卤素原子、氰基或硝基；R11是烷基或烯基，以及其药学上可接受的盐。
• CAMPTOTHECIN ANALOGS AND METHODS OF PREPARATION THEREOF
  申请人：University of Pittsburgh

  公开号：EP1017399A1

  公开（公告）日：2000-07-12
• EP1017399A4
  申请人：——

  公开号：EP1017399A4

  公开（公告）日：2002-11-13