N-fluoren-9-ylmethoxycarbonyl-N-sec-butyl-glycine | 467215-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-fluoren-9-ylmethoxycarbonyl-N-sec-butyl-glycine
• 英文别名: n-(((9h-Fluoren-9-yl)methoxy)carbonyl)-n-(sec-butyl)glycine；2-[butan-2-yl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid
• CAS: 467215-90-3
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: CBLZSQBXEZEKRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  533.1±29.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-fluoren-9-ylmethoxycarbonyl-N-sec-butyl-glycine 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.5h， 生成 4-(sec-butyl)-1,4-diazacycloundecane-2,5-dione
  参考文献：
  名称：

  评估基于氨基酸和羟基酸侧链插入的连续环扩展的可行性。

  摘要：

  基于氨基/羟基酸侧链插入的扩环反应的结果很大程度上取决于环的大小。这份手稿建立在我们之前关于连续环扩展 (SuRE) 方法的工作的基础上，详细介绍了为更好地定义内酰胺和 β-酮酯环系统上这些反应在环大小和附加功能方面的范围和局限性所做的努力。合成结果为哪些底物类别更有可能成功提供了明确的指导，并得到了使用密度泛函理论 (DFT) 方法的计算结果的支持。计算扩环过程中可逆形成的三种异构体的相对吉布斯自由能，使得在大多数情况下能够正确预测新合成反应的可行性。新的合成和计算结果预计将支持新的基于内酰胺和β-酮酯的扩环反应的设计。

  DOI：

  10.1002/chem.202002164
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 N-(2-丁基)甘氨酸乙酯 在 sodium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 以71%的产率得到N-fluoren-9-ylmethoxycarbonyl-N-sec-butyl-glycine
  参考文献：
  名称：

  One dimensional unichemo protection (UCP) in organic synthesis

  摘要：

  描述了一种受保护的模板分子和一种新的一维UniChemo Protection（UCP）有机合成方法，用于制备多功能有机分子。这种合成方法可以与许多种化学反应一起使用，并为模板分子中的许多官能团提供选择性访问。该方法利用由建筑单元组成的保护基团，可以逐个移除这些基团，从而获得一个单位较短的新保护基团或者暴露模板分子上的一个官能团。在模板分子上暴露的官能团可以与目标基团发生反应。通过使用包含不同数量建筑单元的保护基团，可以将不同的目标基团引入模板分子中。

  公开号：

  US20020146684A1

文献信息

• Sequencing of peptoid peptidomimetics by Edman degradation
  作者：Astrid Boeijen、Rob M.J. Liskamp

  DOI：10.1016/s0040-4039(98)00556-5

  日期：1998.5

  The direct identification of resin-bound peptoid peptidomimetics by sequencing is described. The N-terminus of the peptoid was treated with phenyl isothiocyanate, after which the N-terminal peptoid residue was cleaved from the resin as its thiohydantoin derivative. For deduction of the peptoid sequence, the HPLC retention times of the obtained thiohydantoins were compared to those of independently

  描述了通过测序直接鉴定树脂结合的类肽拟肽。用异硫氰酸苯酯处理拟肽的N-末端，然后从树脂上裂解N-末端拟肽残基作为其硫代乙内酰脲衍生物。为了推导类肽序列，将获得的巯基乙内酰脲的HPLC保留时间与独立制备的参考巯基乙内酰脲的HPLC保留时间进行了比较。
• Novel Deltorphin Heptapeptide Analogs with Potent .delta. Agonist, .delta. Antagonist, or Mixed .mu. Antagonist/.delta. Agonist Properties
  作者：Yusuke Sasaki、Takako Chiba

  DOI：10.1021/jm00020a013

  日期：1995.9

  A series of deltorphin (DLT: Tyr-D-Met-Phe-His-Leu-Met-Asp-NH2) analogs in which Leu(5) and/or Met(6) were mainly replaced by t-Leu(Tle) and/or N-alpha-alkylated glycine were synthesized and examined for their receptor binding properties and in vitro bioactivities by guinea pig ileum (GPI) and mouse vas deferens (MVD) assays. [Tle(5)]DLT(2) showed a dramatic decrease in the MVD potency when compared to the parent peptide and was found to have a potent delta receptor antagonist activity against various delta agonists with K-e values of 16-311 nM. Interestingly, the antagonist potency of 2 against DPDPE as agonist was 20-fold weaker than that against deltorphins or Leu-enkephalin. Among the analogs in which Met(6) was replaced by an N-alpha-alkylated Gly residue, [N-alpha-isobutyl-Gly(6)]DLT(5) behaved as a mixed mu antagonist/delta agonist while its isomeric analogs in which the N-alpha-alkyl is n-butyl (4) or (R or S) sec-butyl (6a,b) were very potent delta receptor agonists. Analogs 2, 4, 6a, and 6b were highly stable against rat brain and rat plasma enzymes and thus may represent a starting point for the development of novel receptor-specific compounds useful as ligands for studies of opioid receptors.
• [EN] ONE DIMENSIONAL UNICHEMO PROTECTION (UCP) IN ORGANIC SYNTHESIS<br/>[FR] PROTECTION UNICHEMO (UCP) UNIDIMENSIONNELLE EN SYNTHESE ORGANIQUE
  申请人：CARLSBERG AS

  公开号：WO2002081413A2

  公开（公告）日：2002-10-17

  A protected template molecule and a new one-dimensional UniChemo Protection (UCP) organic synthetic method for preparing polyfunctional organic molecules is described. The synthetic method can be used with many kinds of chemical reactions and provides selective access to many functional groups in a template molecule. The method utilizes protection groups that are each composed of building block units that can be removed one by one affording a new protection group one unit shorter or exposing a functional group on the template molecule. The exposed functional group on the template molecule can react with a target group. Different target groups can be introduced into the template molecule by using protection groups containing different numbers of building block units.
• One dimensional unichemo protection (UCP) in organic synthesis
  申请人：——

  公开号：US20020146684A1

  公开（公告）日：2002-10-10

  A protected template molecule and a new one-dimensional UniChemo Protection (UCP) organic synthetic method for preparing polyfunctional organic molecules is described. The synthetic method can be used with many kinds of chemical reactions and provides selective access to many functional groups in a template molecule. The method utilizes protection groups that are each composed of building block units that can be removed one by one affording a new protection group one unit shorter or exposing a functional group on the template molecule. The exposed functional group on the template molecule can react with a target group. Different target groups can be introduced into the template molecule by using protection groups containing different numbers of building block units.

  描述了一种受保护的模板分子和一种新的一维UniChemo Protection（UCP）有机合成方法，用于制备多功能有机分子。这种合成方法可以与许多种化学反应一起使用，并为模板分子中的许多官能团提供选择性访问。该方法利用由建筑单元组成的保护基团，可以逐个移除这些基团，从而获得一个单位较短的新保护基团或者暴露模板分子上的一个官能团。在模板分子上暴露的官能团可以与目标基团发生反应。通过使用包含不同数量建筑单元的保护基团，可以将不同的目标基团引入模板分子中。
• Evaluating the Viability of Successive Ring‐Expansions Based on Amino Acid and Hydroxyacid Side‐Chain Insertion
  作者：Aggie Lawer、Ryan G. Epton、Thomas C. Stephens、Kleopas Y. Palate、Mahendar Lodi、Emilie Marotte、Katie J. Lamb、Jade K. Sangha、Jason M. Lynam、William P. Unsworth

  DOI：10.1002/chem.202002164

  日期：2020.10

  size. This manuscript, which builds upon our previous work on Successive Ring Expansion (SuRE) methods, details efforts to better define the scope and limitations of these reactions on lactam and β‐ketoester ring systems with respect to ring size and additional functionality. The synthetic results provide clear guidelines as to which substrate classes are more likely to be successful and are supported

  基于氨基/羟基酸侧链插入的扩环反应的结果很大程度上取决于环的大小。这份手稿建立在我们之前关于连续环扩展 (SuRE) 方法的工作的基础上，详细介绍了为更好地定义内酰胺和 β-酮酯环系统上这些反应在环大小和附加功能方面的范围和局限性所做的努力。合成结果为哪些底物类别更有可能成功提供了明确的指导，并得到了使用密度泛函理论 (DFT) 方法的计算结果的支持。计算扩环过程中可逆形成的三种异构体的相对吉布斯自由能，使得在大多数情况下能够正确预测新合成反应的可行性。新的合成和计算结果预计将支持新的基于内酰胺和β-酮酯的扩环反应的设计。