(2-羟基-3-四氢呋喃)-氨基甲酸叔丁酯 | 132872-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: (2-羟基-3-四氢呋喃)-氨基甲酸叔丁酯
• 英文名称: 2-(tert-butoxycarbonylamino)-γ-butyrolactol
• 英文别名: tert-Butyl (2-hydroxyoxolan-3-yl)carbamate；tert-butyl N-(2-hydroxyoxolan-3-yl)carbamate
• CAS: 132872-26-5
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: LHNLDAFOFNSNNF-UHFFFAOYSA-N

物化性质

• 沸点：
  337.5±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  (2-羟基-3-四氢呋喃)-氨基甲酸叔丁酯 在 四丁基碘化铵 、 sodium hydride 、 sodium amide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.25h， 生成 [1-(2-Benzyloxy-ethyl)-3-methyl-but-2-enyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  合成（±）的基础上的新方法-thienamycinβ内酰胺通过4-外-三角函数carbamoylcobalt salophens的环化

  摘要：

  一系列Ñ取代的丙烯基Ñ -benzylcarbamoylcobalt（III）salophens，即11，20和30，已准备，并且已经显示出在一种新的方法，以β内酰胺的前体有用的（即12 - 16，21和31），通过相应的中间氨基甲酰基基团的环化的4- exo - trig模式。从反式-二取代的氮杂环丁烷-2-酮31合成（±）-噻吩霉素1的新形式还描述了通过在甲苯中加热氨基甲酰钴盐酚30一步生产的方法。

  DOI：

  10.1039/p19940000379
• 作为产物：
  描述：

  DL-N-Boc-高丝氨酸甲酯 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以2.0 g的产率得到(2-羟基-3-四氢呋喃)-氨基甲酸叔丁酯
  参考文献：
  名称：

  Novel Angular Benzophenazines:  Dual Topoisomerase I and Topoisomerase II Inhibitors as Potential Anticancer Agents

  摘要：

  A series of substituted angular benzophenazines were prepared using a new synthetic route via a novel regiocontrolled condensation of 1,2-naphthoquinones and 2,3-diaminobenzoic acids. The synthesis and biological activity of this new series of substituted 8,9-benzo[a]phenazine carboxamide systems are described. The analogues were evaluated against the H69 parental human small cell lung carcinoma cell line and H69/LX4 resistant cell line which overexpresses P-glycoprotein. Selected analogues were evaluated against the COR-L23-parental human non small cell lung carcinoma cell line and the COR-L23/R resistant cell line which overexpresses multidrug resistance protein. This series of novel angular benzophenazines were potent cytotoxic agents in these cell lines and may be able to circumvent multidrug resistance mechanisms which result in the lack of efficacy of many drugs in cancer chemotherapy. These compounds show dual inhibition of topoisomerase I and topoisomerase II and thus target two key enzymes responsible for the topology of DNA that are active at different points in the cell cycle. The introduction of chirality into the carboxamide side chain of these novel benzophenazine carboxamides has resulted in the discovery of a potent enantiospecific series of cytotoxic agents, exemplified by 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)methyl-ethyl)-amide, XR11576 ((R)-4j"). In vivo activity has been demonstrated for 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-methyl-ethyl)-amide, XR11576, after intravenous administration to female mice, and this compound has been selected as a development candidate for further evaluation.

  DOI：

  10.1021/jm010329a

文献信息

• A new synthetic route to (±)-thienamycin via 4-exo trigonal cyclisation of carbamoyl cobalt intermediates
  作者：Gerald Pattenden、Stephen J. Reynolds

  DOI：10.1016/0040-4039(91)80870-c

  日期：1991.1

  A new synthesis of (±)-thienamycin (1), based on elaboration of the key intermediate (12) in one step by heating a solution of the carbamoylcobalt salophen (11) in toluene, is described.

  描述了一种新的（±）-噻吩霉素（1）的合成方法，该方法以一步加热关键化合物（12）的方式为基础，方法是加热氨基甲酰钴盐基酚（11）在甲苯中的溶液。
• One-Pot Synthesis of Cyclic Nitrones and Their Conversion to Pyrrolizidines:  7a-<i>e</i><i>pi</i>-Crotanecine Inhibits α-Mannosidases
  作者：S. Cicchi、M. Marradi、P. Vogel、A. Goti

  DOI：10.1021/jo0523518

  日期：2006.2.1

  from the corresponding lactols. Its efficiency relies on the condensation of unprotected hydroxylamine with readily available lactols and on the chemoselectivity of the subsequent esterification with methanesulfonyl chloride. The targeted enantiomerically pure pyrroline N-oxides are versatile synthetic intermediates: one of the nitrones so-obtained has been converted into new polyhydroxypyrrolizidines

  描述了一种新的简单且廉价的一锅法，该方法用于从相应的内酯开始制备对映纯的五元环硝酮。它的效率取决于未保护的羟胺与容易获得的乳糖醇的缩合，以及随后与甲磺酰氯进行酯化反应的化学选择性。靶向的对映体纯的吡咯啉N-氧化物是通用的合成中间体：如此获得的硝酮之一已转化为新的多羟基吡咯烷核苷，生物碱rosmarinecine和crotanecine的类似物，并对其对22种市售糖苷酶的抑制活性进行了分析。其中之一（（-）-7a- epi-crotanecine）是一种有效和选择性的抑制来自千金豆和杏仁的α-甘露糖苷酶的抑制剂。
• Novel Angular Benzophenazines:  Dual Topoisomerase I and Topoisomerase II Inhibitors as Potential Anticancer Agents
  作者：Nigel Vicker、Luke Burgess、Irina S. Chuckowree、Rory Dodd、Adrian J. Folkes、David J. Hardick、Timothy C. Hancox、Warren Miller、John Milton、Sukhjit Sohal、Shouming Wang、Stephen P. Wren、Peter A. Charlton、Wendy Dangerfield、Chris Liddle、Prakash Mistry、Alistair J. Stewart、William A. Denny

  DOI：10.1021/jm010329a

  日期：2002.1.1

  A series of substituted angular benzophenazines were prepared using a new synthetic route via a novel regiocontrolled condensation of 1,2-naphthoquinones and 2,3-diaminobenzoic acids. The synthesis and biological activity of this new series of substituted 8,9-benzo[a]phenazine carboxamide systems are described. The analogues were evaluated against the H69 parental human small cell lung carcinoma cell line and H69/LX4 resistant cell line which overexpresses P-glycoprotein. Selected analogues were evaluated against the COR-L23-parental human non small cell lung carcinoma cell line and the COR-L23/R resistant cell line which overexpresses multidrug resistance protein. This series of novel angular benzophenazines were potent cytotoxic agents in these cell lines and may be able to circumvent multidrug resistance mechanisms which result in the lack of efficacy of many drugs in cancer chemotherapy. These compounds show dual inhibition of topoisomerase I and topoisomerase II and thus target two key enzymes responsible for the topology of DNA that are active at different points in the cell cycle. The introduction of chirality into the carboxamide side chain of these novel benzophenazine carboxamides has resulted in the discovery of a potent enantiospecific series of cytotoxic agents, exemplified by 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)methyl-ethyl)-amide, XR11576 ((R)-4j"). In vivo activity has been demonstrated for 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-methyl-ethyl)-amide, XR11576, after intravenous administration to female mice, and this compound has been selected as a development candidate for further evaluation.
• Synthesis of (±)-thienamycin based on a new approach to β-lactams via 4-exo-trig cyclisation of carbamoylcobalt salophens
  作者：Gerald Pattenden、Stephen J. Reynolds

  DOI：10.1039/p19940000379

  日期：——

  been shown to be useful precursors in a new approach to β-lactams (viz.12-16, 21 and 31), via 4-exo-trig modes of cyclisation of the corresponding intermediate carbamoyl radicals. A new formal synthesis of (±)-thienamycin 1 from the trans-disubstituted azetidin-2-one 31 produced in one step by heating the carbamoylcobalt salophen 30 in toluene, is also described.

  一系列Ñ取代的丙烯基Ñ -benzylcarbamoylcobalt（III）salophens，即11，20和30，已准备，并且已经显示出在一种新的方法，以β内酰胺的前体有用的（即12 - 16，21和31），通过相应的中间氨基甲酰基基团的环化的4- exo - trig模式。从反式-二取代的氮杂环丁烷-2-酮31合成（±）-噻吩霉素1的新形式还描述了通过在甲苯中加热氨基甲酰钴盐酚30一步生产的方法。