4-(prop-2-yn-1-yloxy)cyclohexan-1-ol | 1447817-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(prop-2-yn-1-yloxy)cyclohexan-1-ol
• 英文别名: 4-Prop-2-ynoxycyclohexan-1-ol；4-prop-2-ynoxycyclohexan-1-ol
• CAS: 1447817-83-5
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: OCWDNUHEYOSNJT-UHFFFAOYSA-N

物化性质

• 沸点：
  264.9±30.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(prop-2-yn-1-yloxy)cyclohexan-1-ol 在 sodium acetate 、 乙酸酐 、 pyridinium chlorochromate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.5h， 生成 1-ethyl-2-(2-(3-(2-(1-ethyl-3,3-dimethylindolin-2-ylidene)ethylidene)-2-(ethylamino)-5-(prop-2-yn-1-yloxy)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-3H-indol-1-ium chloride
  参考文献：
  名称：

  Folate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery

  摘要：

  A series of heptamethine cyanine (1-3) derivatives bearing a carbamate ethyl disulfide group and gemcitabine, an anticancer drug, have been newly synthesized. Their disulfide bonds are readily cleaved by various thiols including glutathione, to result in a subsequent decomposition of the carbamate into amine followed by release of the active gemcitabine, which can be monitored by the fluorescence changes. In the biological experiment, prodrug 1 is preferentially up-taken by folate-positive KB cells over folate-negative A549 cells via receptor-mediated endocytosis to release gemcitabine causing cell death and to emit fluorescence in endoplasmic reticulum. Moreover, it is selectively accumulated in the KB cells which were treated to mice by dorsal subcutaneous injection. This drug delivery system is a new theranostic agent, wherein both therapeutic effect and drug uptake can be easily monitored at the subcellular level, by in vivo and in vitro fluorescence imaging.

  DOI：

  10.1021/ja405372k
• 作为产物：
  描述：

  1,4-环己二醇 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(prop-2-yn-1-yloxy)cyclohexan-1-ol
  参考文献：
  名称：

  针对可生物降解聚合物的新型ε-己内酯二炔单体

  摘要：

  环己烷-1，4-二醇与炔丙基溴的取代反应得到4-（prop-2-yn-1-yloxy）环己醇。将该化合物氧化成相应的酮（2- C 2 H），然后氧化成乙炔γ-取代的ε-己内酯（3 - C 2 H）。后者化合物链延长两个丁二单体：对称5,5' - [己-2,4-二炔-1,6-二基双（氧基）]双（oxepan-2-酮）（3 -C 4 - 3）和不对称的5-{[5-（三甲基甲硅烷基）penta-2,4-二炔-1-基]氧基}氧杂潘-2-酮（3 -C 4TMS）分别通过Eglinton和Cadiot–Chodkiewicz耦合。通过即时酮前体的替代拜尔-维利格氧化，得到两种化合物2 -C 4 - 2和2 -C 4 TMS。

  DOI：

  10.1016/j.tetlet.2013.08.080

文献信息

• Harnessing Hypoxia‐Dependent Cyanine Photocages for In Vivo Precision Drug Release
  作者：Yutao Zhang、Chenxu Yan、Qiaoqiao Zheng、Qian Jia、Zhongliang Wang、Ping Shi、Zhiqian Guo

  DOI：10.1002/anie.202017349

  日期：2021.4.19

  manipulation of this hypoxia‐dependent photocaging and dual‐modal optical signals in living cells and tumor‐bearing mice, making a breakthrough in the direct spatiotemporal control and in vivo feedback regulation. This unique photoactivation mechanism overcomes the limitation of hypoxia, which allows site‐specific remote control for targeted therapy, and expands the photo‐trigger toolbox for on‐demand drug

  Photocaging 有望在空间和时间中精确操纵生物事件。然而，目前的近红外 (NIR) 光笼的光解依赖于氧，并且缺乏及时的反馈调节，这已被证明是靶向治疗的主要瓶颈。在此，我们提出了二烷基胺取代花青（Cy-NH）的缺氧依赖性光活化机制，伴随着发射片段的产生，并通过逆合成和光谱分析进行了验证。我们首次在活细胞和荷瘤小鼠中实现了这种缺氧依赖性光笼和双模光信号的正交操作，在直接时空控制和体内反馈调节方面取得了突破。这种独特的光活化机制克服了缺氧的限制，
• New ε-caprolactone diyne monomers aiming for biodegradable polymers
  作者：Bartłomiej Pigulski、Nurbey Gulia、Sławomir Szafert

  DOI：10.1016/j.tetlet.2013.08.080

  日期：2013.11

  two butadiynyl monomers: symmetrical 5,5′-[hexa-2,4-diyne-1,6-diylbis(oxy)]bis(oxepan-2-one) (3-C4-3) and unsymmetrical 5-[5-(trimethylsilyl)penta-2,4-diyn-1-yl]oxy}oxepan-2-one (3-C4TMS) via Eglinton and Cadiot–Chodkiewicz couplings, respectively. Both compounds were obtained through an alternative Baeyer–Villiger oxidation of immediate ketone precursors 2-C4-2 and 2-C4TMS.

  环己烷-1，4-二醇与炔丙基溴的取代反应得到4-（prop-2-yn-1-yloxy）环己醇。将该化合物氧化成相应的酮（2- C 2 H），然后氧化成乙炔γ-取代的ε-己内酯（3 - C 2 H）。后者化合物链延长两个丁二单体：对称5,5' - [己-2,4-二炔-1,6-二基双（氧基）]双（oxepan-2-酮）（3 -C 4 - 3）和不对称的5-[5-（三甲基甲硅烷基）penta-2,4-二炔-1-基]氧基}氧杂潘-2-酮（3 -C 4TMS）分别通过Eglinton和Cadiot–Chodkiewicz耦合。通过即时酮前体的替代拜尔-维利格氧化，得到两种化合物2 -C 4 - 2和2 -C 4 TMS。
• Folate-Based Near-Infrared Fluorescent Theranostic Gemcitabine Delivery
  作者：Zhigang Yang、Jae Hong Lee、Hyun Mi Jeon、Ji Hye Han、Nayoung Park、Yanxia He、Hyunseung Lee、Kwan Soo Hong、Chulhun Kang、Jong Seung Kim

  DOI：10.1021/ja405372k

  日期：2013.8.7

  A series of heptamethine cyanine (1-3) derivatives bearing a carbamate ethyl disulfide group and gemcitabine, an anticancer drug, have been newly synthesized. Their disulfide bonds are readily cleaved by various thiols including glutathione, to result in a subsequent decomposition of the carbamate into amine followed by release of the active gemcitabine, which can be monitored by the fluorescence changes. In the biological experiment, prodrug 1 is preferentially up-taken by folate-positive KB cells over folate-negative A549 cells via receptor-mediated endocytosis to release gemcitabine causing cell death and to emit fluorescence in endoplasmic reticulum. Moreover, it is selectively accumulated in the KB cells which were treated to mice by dorsal subcutaneous injection. This drug delivery system is a new theranostic agent, wherein both therapeutic effect and drug uptake can be easily monitored at the subcellular level, by in vivo and in vitro fluorescence imaging.