5-[(2-Methylpropan-2-yl)oxycarbonylamino]pentyl 2-cyanoacetate | 1309612-67-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-[(2-Methylpropan-2-yl)oxycarbonylamino]pentyl 2-cyanoacetate
• CAS: 1309612-67-6
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: RRVHPYHTYMFLTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2-Methylpropan-2-yl)oxycarbonylamino]pentyl 2-cyanoacetate 在 4-二甲氨基吡啶 、 苯甲醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 5-[(7-methoxy-2-oxochromene-3-carbonyl)amino]pentyl 2-cyano-3-[5-(dihexylamino)thiophen-2-yl]prop-2-enoate
  参考文献：
  名称：

  Self-calibrating viscosity probes: Design and subcellular localization

  摘要：

  We describe the design, synthesis and fluorescence profiles of new self-calibrating viscosity dyes in which a coumarin (reference fluorophore) has been covalently linked with a molecular rotor (viscosity sensor). Characterization of their fluorescence properties was made with separate excitation of the units and through resonance energy transfer from the reference to the sensor dye. We have modified the linker and the substitution of the rotor in order to change the hydrophilicity of these probes thereby altering their subcellular localization. For instance, hydrophilic dye 12 shows a homogeneous distribution inside the cell and represents a suitable probe for viscosity measurements in the cytoplasm. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.026
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 、 氰乙酸 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 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以33%的产率得到5-[(2-Methylpropan-2-yl)oxycarbonylamino]pentyl 2-cyanoacetate
  参考文献：
  名称：

  Synthesis and evaluation of self-calibrating ratiometric viscosity sensors

  摘要：

  我们描述了一系列自校准染料的设计、合成及荧光特性，以提供流体粘度的比率测量。该设计基于将一种主要荧光基团（参考荧光基团）共价连接到一种具有粘度敏感性荧光发射的次要荧光基团（传感器）的方式，前者的荧光发射与粘度无关。我们通过对这两个单元的独立激励以及通过共振能量转移从参考荧光基团到传感器荧光基团，来表征其荧光特性。我们评估了两个荧光基团的化学结构以及连接段的长度，以优化粘度测量的整体亮度和灵敏度。我们还展示了这种比率染料在脂质体模型中检测膜粘度变化的应用。

  DOI：

  10.1039/c0ob01042a

文献信息

• Synthesis and evaluation of self-calibrating ratiometric viscosity sensors
  作者：Hyung-Jo Yoon、Marianna Dakanali、Darcy Lichlyter、Willy M. Chang、Karen A. Nguyen、Matthew E. Nipper、Mark A. Haidekker、Emmanuel A. Theodorakis

  DOI：10.1039/c0ob01042a

  日期：——

  We describe the design, synthesis and fluorescent profile of a family of self-calibrating dyes that provide ratiometric measurements of fluid viscosity. The design is based on covalently linking a primary fluorophore (reference) that displays a viscosity-independent fluorescence emission with a secondary fluorophore (sensor) that exhibits a viscosity-sensitive fluorescence emission. Characterization of fluorescent properties was made with separate excitation of the units and through Resonance Energy Transfer from the reference to the sensor dye. The chemical structures of both fluorophores and the linker length have been evaluated in order to optimize the overall brightness and sensitivity of the viscosity measurements. We also present an application of such ratiometric dyes for the detection of membrane viscosity changes in a liposome model.

  我们描述了一系列自校准染料的设计、合成及荧光特性，以提供流体粘度的比率测量。该设计基于将一种主要荧光基团（参考荧光基团）共价连接到一种具有粘度敏感性荧光发射的次要荧光基团（传感器）的方式，前者的荧光发射与粘度无关。我们通过对这两个单元的独立激励以及通过共振能量转移从参考荧光基团到传感器荧光基团，来表征其荧光特性。我们评估了两个荧光基团的化学结构以及连接段的长度，以优化粘度测量的整体亮度和灵敏度。我们还展示了这种比率染料在脂质体模型中检测膜粘度变化的应用。
• Self-calibrating viscosity probes: Design and subcellular localization
  作者：Marianna Dakanali、Thai H. Do、Austin Horn、Akaraphon Chongchivivat、Tuptim Jarusreni、Darcy Lichlyter、Gianni Guizzunti、Mark A. Haidekker、Emmanuel A. Theodorakis

  DOI：10.1016/j.bmc.2012.05.026

  日期：2012.7

  We describe the design, synthesis and fluorescence profiles of new self-calibrating viscosity dyes in which a coumarin (reference fluorophore) has been covalently linked with a molecular rotor (viscosity sensor). Characterization of their fluorescence properties was made with separate excitation of the units and through resonance energy transfer from the reference to the sensor dye. We have modified the linker and the substitution of the rotor in order to change the hydrophilicity of these probes thereby altering their subcellular localization. For instance, hydrophilic dye 12 shows a homogeneous distribution inside the cell and represents a suitable probe for viscosity measurements in the cytoplasm. (C) 2012 Elsevier Ltd. All rights reserved.