2-乙酸苯甲酸叔丁酯 | 168072-81-9

• 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-乙酸苯甲酸叔丁酯
• 英文名称: 2-Carboxymethyl-benzoic acid tert-butyl ester
• 英文别名: 2-[2-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]acetic acid
• CAS: 168072-81-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: FVHGXAUPJLPAKC-UHFFFAOYSA-N

物化性质

• 沸点：
  376.3±25.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-乙酸苯甲酸叔丁酯 在 叠氮磷酸二苯酯 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成
  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：

  2-(2-(allyloxy)-2-oxoethyl)benzoic acid 在 吗啉 、 四(三苯基膦)钯 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-乙酸苯甲酸叔丁酯
  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

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。
• COMPOSITIONS OF LIPOPEPTIDE ANTIBIOTIC DERIVATIVES AND METHODS OF USE THEREOF
  申请人：MIGENIX INC.

  公开号：EP1656390A2

  公开（公告）日：2006-05-17
• [EN] COMPOSITIONS OF LIPOPEPTIDE ANTIBIOTIC DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] COMPOSITIONS A BASE DE DERIVES ANTIBIOTIQUES DE LA CLASSE DES LIPOPEPTIDES ET LEURS METHODES D'UTILISATION
  申请人：MICROLOGIX BIOTECH INC

  公开号：WO2005000878A2

  公开（公告）日：2005-01-06

  The present invention provides derivatives of lipopeptide antibiotics that display antimicrobial activity against microorganisms, methods and compounds for synthesizing such antimicrobial derivatives and analogues, and methods of using the compounds in a variety of contexts, including in the treatment and prevention of microbial infections.
• 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).