2-叔丁氧基羰氨基-4,5-二甲氧基苯甲酸 | 122744-78-9

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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-叔丁氧基羰氨基-4,5-二甲氧基苯甲酸
• 英文名称: 2-((tert-Butoxycarbonyl)amino)-4,5-dimethoxybenzoic acid
• 英文别名: 4,5-dimethoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]benzoic acid
• CAS: 122744-78-9
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: ZXNOFBMUVBIGOE-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±42.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S24/25
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-叔丁氧基羰氨基-4,5-二甲氧基苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-N-cyclohexyl-4,5-dimethoxybenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of benzamides and benzamidines: structural requirement of a pyrimidine ring for inhibition of EGFR tyrosine kinase

  摘要：

  The benzamides 1 and the benzamidines 2-3 were synthesized as the mimics of 4-anilinoquinazolines, which possess inhibition of epidermal growth factor receptor (EGER) tyrosine kinase, and tested for cytotoxicity toward A431 and inhibitory activity toward autophosphorylation by the enzyme assay. High cell growth inhibition was observed in a series of the cyclic benzamides 3: the IC50 values are 0.09-0.32 mM. The benzamidines 3a and 3b exhibited high inhibition of EGER tyrosine kinase at a 1.0 muM concentration, although the benzamides 1 and the benzamidines 2 did not show significant kinase inhibition at a 10 muM concentration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.001
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-氨基-4,5-二甲氧基苯甲酸 以 甲醇 为溶剂， 反应 24.0h， 生成 2-叔丁氧基羰氨基-4,5-二甲氧基苯甲酸
  参考文献：
  名称：

  新型N（9）甲基化AHMA类似物的合成与抗肿瘤活性†

  摘要：

  描述了一种新型抗肿瘤N（9）-甲基-3-（9-amino啶基氨基）-5-羟甲基苯胺（AHMA）衍生物的合成方法。氨基苯甲酸的Boc保护，然后LiAlH 4还原，得到了新颖的甲基氨基苄醇反应物。他们与9-氯ac啶提供N（9）-甲基化的AHMA衍生物用于生物筛选。针对七种癌细胞系的初步抗增殖试验确定了具有低μMIC 50值的化合物。

  DOI：

  10.1039/c2nj40567a

文献信息

• Use of Cyclohexylisocyanide and Methyl 2-Isocyanoacetate as Convertible Isocyanides for Microwave-Assisted Fluorous Synthesis of 1,4-Benzodiazepine-2,5-dione Library
  作者：Hongyu Zhou、Wei Zhang、Bing Yan

  DOI：10.1021/cc900157w

  日期：2010.1.11

  A new protocol in which cyclohexylisocyanide and methyl 2-isocyanoacetate are used as convertible isocyanides for Ugi/de-Boc/cyclization/Suzuki synthesis of biaryl-substituted 1,4-benzodiazepine-2,5-diones has been developed. Ugi reactions of Boc-protected anthranilic acids, fluorous benzaldehydes, amines, and cyclohexylisocyanide or methyl 2-isocyanoacetate were carried out at room temperature. Microwave-promoted

  已经开发了一种新的方案，其中环己基异氰酸酯和2-异氰基乙酸甲酯被用作可转换的异氰酸酯，用于Ugi / de-Boc /环化/ Suzuki合成联芳基取代的1,4-苯并二氮杂-2,5-二酮。Boc保护的邻氨基苯甲酸，氟苯甲醛，胺和环己基异氰酸酯或2-异氰基乙酸甲酯的Ugi反应在室温下进行。微波促进的de-Boc /环化反应得到1,4-苯并二氮杂-2,5-二酮（BZDs）。Suzuki偶联反应通过去除氟标签并引入联芳基进一步使BZD环衍生化。通过微波辅助溶液相荧光平行合成，制备了一个包含四个多样性点的三十三元联芳基取代的BZD库。
• Synthesis of a quinolone library from ynones
  作者：Timothy R. Ward、Brandon J. Turunen、Torsten Haack、Benjamin Neuenswander、William Shadrick、Gunda I. Georg

  DOI：10.1016/j.tetlet.2009.09.024

  日期：2009.11

  A library of 72 quinolones was synthesized from substituted anthranilic acids, using ynone intermediates. These masked beta-dicarbonyl synthons allowed cyclization under milder conditions than previously reported quinolone syntheses. (C) 2009 Elsevier Ltd. All rights reserved
• Benzamides and benzamidines as specific inhibitors of epidermal growth factor receptor and v-Src protein tyrosine kinases
  作者：Toru Asano、Tomohiro Yoshikawa、Taikou Usui、Hiroshi Yamamoto、Yoshinori Yamamoto、Yoshimasa Uehara、Hiroyuki Nakamura

  DOI：10.1016/j.bmc.2004.04.030

  日期：2004.7

  The benzamides 1 and the benzamidines 2 as well as the cyclic benzamidines 3 were designed and synthesized as the mimics of 4-anilinoquinazolines for an inhibitor of EGFR tyrosine kinase. The specific inhibitions of EGFR tyrosine kinase were observed in the benzamides 1c and 1d, and the benzamidine 2a, whereas the specific inhibitions of v-Src kinase were observed in the benzamide 1j and the benzamidine 2d at a 10 mug/mL concentration of compounds. The cyclic benzamidines 3a and 3b showed potent kinase inhibition of EGFR at a 1.0 mug/mL concentration. According to the docking simulation using the X-ray structure of EGFR kinase domain in complex with erlotimb, the LigScore2 scoring function value of erlotimb was calculated as 5.61, whereas that of the benzamide 1c was 5.05. In a similar manner, the LigScore2 value of the cyclic benzamidine 3a was calculated as 5.10. (C) 2004 Elsevier Ltd. All rights reserved.
• Novel applications of resin bound α-amino acids for the synthesis of benzodiazepines (via Wang resin) and ketopiperazines (via hydroxymethyl resin)
  作者：Christopher Hulme、Liang Ma、N.Vasant Kumar、Paul H Krolikowski、Andrew C Allen、Richard Labaudiniere

  DOI：10.1016/s0040-4039(99)02326-6

  日期：2000.3

  This communication reveals a novel application of resin bound oc-amino acids coupled with the UDC (Ugi/DeBOC/cyclize) strategy. Reaction with either N-BOC-alpha-amino aldehydes or N-BOC anthranilic acids and subsequent acid treatment allows the preparation of highly pure and diverse arrays (approx. 10000 in size) of 1,4-benzodiazepines (Wang resin) and ketopiperazines (hydroxymethyl resin), respectively. Notable for the benzodiazepine series of compounds are the five potential points of diversity available from this two-step protocol. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Secondary .beta.-aminobenzamide and heteroatom directed lithiation in the synthesis of 5,6-dimethoxyanthranilamides and related compounds
  作者：Stefan Bengtsson、Thomas Hoegberg

  DOI：10.1021/jo00280a020

  日期：1989.9