2-(2-(allyloxy)-2-oxoethyl)benzoic acid | 168072-80-8

• 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: 2-(2-(allyloxy)-2-oxoethyl)benzoic acid
• 英文别名: allyl 2-(carboxylic acid)phenylacetate；2-(2-Oxo-2-prop-2-enoxyethyl)benzoic acid
• CAS: 168072-80-8
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: AVJRUARGRORZGR-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  361.1±22.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(allyloxy)-2-oxoethyl)benzoic acid 在 吗啉 、 四(三苯基膦)钯 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(2-carboxymethyl-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  β-Glucuronyl carbamate based pro-moieties designed for prodrugs in ADEPT

  摘要：

  A number of pro-moieties 8a - e designed for prodrug preparation have been synthesized (chart 2). The pro-moieties, containing a glucuronyl carbamate group linked to a spacer possessing a terminal carboxylic acid group, have been synthesized from isocyanates 6 and anomerically unprotected glucuronic acids 10 (chart 2). The requisite isocyanates had to be prepared using the Curtius rearrangement. Glucuronyl carbamates proved to be excellent substrates for human beta-glucuronidase. The pro-moieties 8a - e can be coupled to hydroxy- or amino group containing drugs. The resulting prodrugs are designed to be activated by beta-glucuronidase (chart 1) and to be used in ADEPT. Application is demonstrated with the synthesis of daunomycin prodrugs 12a - e (chart 3).

  DOI：

  10.1016/0040-4039(95)00049-i
• 作为产物：
  描述：

  高邻苯二甲酸酐 、 烯丙醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以83%的产率得到2-(2-(allyloxy)-2-oxoethyl)benzoic acid
  参考文献：
  名称：

  Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT

  摘要：

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00249-0

文献信息

• Highly Diastereoselective Synthesis of Anomeric β-O-Glycopyranosyl Carbamates from Isocyanates
  作者：Ruben G. G. Leenders、Rob Ruytenbeek、Eric W. P. Damen、Hans W. Scheeren

  DOI：10.1055/s-1996-4377

  日期：1996.11

  1-β-O-Glycopyranosyl carbamates are prepared with practically 100% β-diastereoselectivity from anomerically unprotected glycopyranosides and isocyanates. The isocyanates are prepared in situ from carboxylic acids via acyl azides.

  1-β-O-Glycopyranosyl carbamates 是通过在几乎 100% β-对映选择性下，从无保护的α-糖苷和异氰酸酯制备的。异氰酸酯则是由羧酸通过酰基叠氮化物原位制备得来的。
• Highly Chemoselective Esterification Reactions and Boc/THP/TBDMS Discriminating Deprotections under Samarium(III) Catalysis
  作者：Pushparathinam Gopinath、Surapaneni Nilaya、Kannoth Manheri Muraleedharan

  DOI：10.1021/ol200247c

  日期：2011.4.15

  The usefulness of SmCl(3) as an excellent catalyst for chemoselective esterifications and selective removal of acid sensitive protecting groups such as Boc, THP, and TBDMS in the presence of one another is demonstrated through suitable examples.
• β-Glucuronyl carbamate based pro-moieties designed for prodrugs in ADEPT
  作者：Ruben G.G. Leenders、Kasper A.A. Gerrits、Rob Ruijtenbeek、Hans W. Scheeren、Hidde J. Haisma、Epie Boven

  DOI：10.1016/0040-4039(95)00049-i

  日期：1995.3

  A number of pro-moieties 8a - e designed for prodrug preparation have been synthesized (chart 2). The pro-moieties, containing a glucuronyl carbamate group linked to a spacer possessing a terminal carboxylic acid group, have been synthesized from isocyanates 6 and anomerically unprotected glucuronic acids 10 (chart 2). The requisite isocyanates had to be prepared using the Curtius rearrangement. Glucuronyl carbamates proved to be excellent substrates for human beta-glucuronidase. The pro-moieties 8a - e can be coupled to hydroxy- or amino group containing drugs. The resulting prodrugs are designed to be activated by beta-glucuronidase (chart 1) and to be used in ADEPT. Application is demonstrated with the synthesis of daunomycin prodrugs 12a - e (chart 3).
• Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT
  作者：Dries B.A. de Bont、Ruben G.G. Leenders、Hidde J. Haisma、Ida van der Meulen-Muileman、Hans W. Scheeren

  DOI：10.1016/s0968-0896(96)00249-0

  日期：1997.2

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.