(2-氯乙酰基)氨基甲酸苄酯 | 16001-64-2

• 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: (2-氯乙酰基)氨基甲酸苄酯
• 英文名称: benzyl 2-chloroacetylcarbamate
• 英文别名: PCM-0102153；Benzyl-chloracetylcarbamat；Benzyl chloroacetylcarbamate；benzyl N-(2-chloroacetyl)carbamate
• CAS: 16001-64-2
• 化学式: C₁₀H₁₀ClNO₃
• mdl: MFCD07348581
• 分子量: 227.647
• InChiKey: PFOQENPGHAIKIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (2-氯乙酰基)氨基甲酸苄酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (E)-benzyl 4-(benzyloxy)-but-2-enoylcarbamate
  参考文献：
  名称：

  Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

  摘要：

  一种光学活性的四氢喹啉中间体（5）经过8个步骤由单保护的乙二醇制备而成，使用钯催化的氮-迈克尔反应来引入手性。该中间体可以转化为三种Galipea生物碱（角度线碱、加利碱和库斯帕碱）。邻近的苄氧基团在合成的多个步骤中被发现对反应有显著影响。

  DOI：

  10.1039/c2ob25122a

文献信息

• 1,2,4-Triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
  申请人：GLAXO GROUP LIMITED

  公开号：EP0070097A1

  公开（公告）日：1983-01-19

  This invention relates to compounds of the general formula (I) and physiologically acceptable salts, hydrates and bioprecursors thereof in which R1 represents C1-14 alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heteroaralkyl, trifluoroalkyl or alkyl substituted by hydroxy, alkoxy, amino, alkylamino, dialkylamino or cycloalkyl; and R2 represents hydrogen or C1-4 alkyl; or R1 and R2 may together with the nitrogen atom to which they are attached form a 5 to 10 membered ring which may be saturated or may contain at least one double bond, may be unsubstituted or may be substituted by one or more C1-3 alkyl groups or a hydroxy group and/or may contain another heteroatom which is oxygen or sulphur; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or tiophen ring in which incorporation into the rest of the molecule is through bonds at the 2-and 5-positions, the furan or thiophen optionally bearing a further substituent R6 adjacent to the group R1R2N-Alk; or Q represents a tiophen ring in which incorporation into the rest of the molecule is through bonds at the 2- and 4- positions, the tiophen ring optionally bearing a further substituent R6 adjacent to the group R1R2N-Alk with the proviso that when the group R1R2NAlk is in the 4-position then the group R6 is in the 5-position; or Q represents a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R6 represents halogen or C1-4 alkyl which may be substituted by hydroxy or C1-4 alkoxy; X represents oxygen, sulphur, -NH-, methylene or a bond; n represents zero, 1 or 2; and m represents an integer from 2 to 5; with the proviso that when X represents -NH- then Q is a benzene ring; R3 represents hydrogen, alkyl, alkenyl, aralkyl, or C2-6 alkyl substituted by hydroxy or alkoxy; Alk" represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms; R4 represents the group -ZCORs where R5 represents hydroxy or alkoxy or the group in which the symbols R1', R2', Alk', Q', n', X', n' and R3' have meanings which are as defined above for the symbols R1, R2, Alk, Q, n, X, m and R3 respectively but which, in each case, may be the same as or different to the meaning of the latter symbol; Alkb represents a straight or branched alkylene chain containing from 1 to 6 carbon atoms; Z represents an alkylene chain containing from 1 to 16 carbon atoms optionally substituted by one or two C1-3 alkyl groups and optionally containing a double or triple bond; or optionally interrupted by a heteroatom, or by a disulphide (S-S) group; or optionally interrupted by a cycloalkyl or a phenyl group, or Z represents a cycloalkyl or a phenyl group; or R4 represents a C1-6 straight or branched hydroxyalkyl group (optionally substituted by hydroxy or amino) or an aminoalkyl group (optionally substituted by amino, SH, C02H or aryl). The compounds show pharmacological activity as selective histamine H2-antagonists.

  本发明涉及通式 (I) 的化合物 及其生理上可接受的盐、水合物和生物前体，其中 R1 代表 C1-14 烷基、环烷基、烯基、炔基、芳基、杂烷基、三氟烷基或被羟基、烷氧基、氨基、烷基氨基、二烷基氨基或环烷基取代的烷基；R2 代表氢或 C1-4 烷基；或 R1 和 R2 可与它们所连接的氮原子一起形成一个 5 至 10 个成员的环，该环可以是饱和的，也可以含有至少一个双键，可以是未取代的，也可以是被一个或多个 C1-3 烷基或羟基取代的，和/或可以含有另一个氧或硫的杂原子； 烷基代表 1-6 个碳原子的直链或支链亚烷基； Q 代表呋喃或噻吩环，通过 2 位和 5 位上的键与分子的其余部分结合，该呋喃或噻吩环可选 择在基团 R1R2N-Alk 附近带有另一个取代基 R6；或 Q 代表噻吩环，通过 2-和 4-位的键与分子的其余部分结合，噻吩环可选择带有与基团 R1R2N-Alk 相邻的另一个取代基 R6，但当基团 R1R2NAlk 位于 4-位时，基团 R6 位于 5-位；或 Q 代表苯环，通过 1-和 3-位或 1-和 4-位的键与分子的其余部分结合； R6 代表卤素或可被羟基或 C1-4 烷氧基取代的 C1-4 烷基； X 代表氧、硫、-NH-、亚甲基或键； n 代表零、1 或 2；m 代表 2 至 5 的整数；但当 X 代表-NH- 时，Q 为苯环； R3 代表氢、烷基、烯基、芳烷基或被羟基或烷氧基取代的 C2-6 烷基； 烷基 "代表含有 1 至 6 个碳原子的直链或支链亚烷基链； R4 代表基团-ZCORs，其中 R5 代表羟基或烷氧基或基团 其中符号 R1'、R2'、Alk'、Q'、n'、X'、n'和 R3' 的含义分别与上文符号 R1、R2、Alk、Q、n、X、m 和 R3 所定义的含义相同，但在每种情况下，可与后一符号的含义相同或不同； Alkb 代表含有 1 至 6 个碳原子的直链或支链亚烷基链； Z 代表含有 1 至 16 个碳原子的亚烷基链，可任选被一个或两个 C1-3 烷基取代，并可任选含有双键或三键；或可任选被杂原子或二硫化物 (S-S) 基团打断；或可任选被环烷基或苯基打断，或 Z 代表环烷基或苯基；或 R4 代表 C1-6 直链或支链羟烷基（可选择被羟基或氨基取代）或氨基烷基（可选择被氨基、SH、C02H 或芳基取代）。 这些化合物具有选择性组胺 H2- 拮抗剂的药理活性。
• US4476126A
  申请人：——

  公开号：US4476126A

  公开（公告）日：1984-10-09
• Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction
  作者：Laura L. Taylor、Frederick W. Goldberg、King Kuok (Mimi) Hii

  DOI：10.1039/c2ob25122a

  日期：——

  An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.

  一种光学活性的四氢喹啉中间体（5）经过8个步骤由单保护的乙二醇制备而成，使用钯催化的氮-迈克尔反应来引入手性。该中间体可以转化为三种Galipea生物碱（角度线碱、加利碱和库斯帕碱）。邻近的苄氧基团在合成的多个步骤中被发现对反应有显著影响。