diethyl 3,5-dimethyl-4-nitrobenzylphosphonate | 864513-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl 3,5-dimethyl-4-nitrobenzylphosphonate
• 英文别名: 5-(diethoxyphosphorylmethyl)-1,3-dimethyl-2-nitrobenzene
• CAS: 864513-22-4
• 化学式: C₁₃H₂₀NO₅P
• 分子量: 301.279
• InChiKey: CFGCCMJCPPLFTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  425.0±33.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 3,5-dimethyl-4-nitrobenzylphosphonate 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 40.5h， 生成
  参考文献：
  名称：

  A double bond-conjugated dimethylnitrobenzene-type photolabile nitric oxide donor with improved two-photon cross section

  摘要：

  Photocontrollable NO donors enable precise spatiotemporal release of NO under physiological conditions. We designed and synthesized a novel dimethylnitrobenzene-type NO donor, Flu-DNB-DB, which contains a carbon-carbon double bond in place of the amide bond of previously reported Flu-DNB. Flu-DNB-DB releases NO in response to one-photon activation in the blue wavelength region, and shows a greatly increased two-photon cross-section (delta(u)) at 720 nm (Flu-DNB: 0.12 GM, Flu-DNB-DB: 0.98 GM). We show that Flu-DNB-DB enables precisely controlled intracellular release of NO in response to 950 nm pulse laser irradiation for as little as 1 s. This near-infrared-light-controllable NO source should be a valuable tool for studies on the biological roles of NO. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.05.095
• 作为产物：
  描述：

  4-硝基-3,5-二甲基苯甲酸 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三溴化磷 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 diethyl 3,5-dimethyl-4-nitrobenzylphosphonate
  参考文献：
  名称：

  Peroxynitrite generation from a NO-releasing nitrobenzene derivative in response to photoirradiation

  摘要：

  证明了从硝基苯衍生物中能够光控生成ONOO−。所设计的化合物在光照射下释放NO，生成的亚醌将分子氧还原生成O2˙−；这两者的反应生成ONOO−，通过ONOO−荧光探针HKGreen-3得以确认。

  DOI：

  10.1039/c1cc11681a

文献信息

• Visible light-induced nitric oxide release from a novel nitrobenzene derivative cross-conjugated with a coumarin fluorophore
  作者：Kai Kitamura、Naoya Ieda、Kazuhiro Hishikawa、Takayoshi Suzuki、Naoki Miyata、Kiyoshi Fukuhara、Hidehiko Nakagawa

  DOI：10.1016/j.bmcl.2014.10.075

  日期：2014.12

  dimethylnitrobenzene derivatives conjugated with coumarins were designed, synthesized and evaluated as photocontrollable NO donors. The optical properties and efficiency of photo-induced NO release were dependent upon the nature of the conjugation system. One of these compounds, Bhc-DNB (1), showed spatiotemporally well-controlled NO release in cultured cells upon exposure to light in the less-cytotoxic visible

  一氧化氮（NO）是内源性生物合成的众所周知的自由基分子，在哺乳动物中显示出各种功能。为了研究NO功能，可控NO供体，即响应于光而释放NO的化合物，有望潜在地有用。然而，大多数常规的NO供体需要有害的紫外线来释放NO。在这项研究中，设计，合成和评估了两种与香豆素共轭的二甲基硝基苯衍生物，作为光可控的NO供体。光诱导NO释放的光学性质和效率取决于缀合系统的性质。这些化合物之一Bhc-DNB（1）显示，在暴露于细胞毒性较小的可见光波长范围（400-430 nm）的光中时，培养细胞的NO释放在时空上得到了很好的控制。
• Photoinduced Nitric Oxide Release from Nitrobenzene Derivatives
  作者：Takayoshi Suzuki、Osamu Nagae、Yuka Kato、Hidehiko Nakagawa、Kiyoshi Fukuhara、Naoki Miyata

  DOI：10.1021/ja0512024

  日期：2005.8.24

  A new type of photoinduced nitric oxide (NO) donors was designed from nitrobenzene derivatives. Visible-light irradiation of 2,6-dimethylnitrobenzenes bearing extended pi-electron systems at the 4-position revealed efficient NO release using ESR analysis and the Griess assay. Computational study and ultraviolet spectrum analysis suggested that the NO-releasing activity was closely related to the conformation

  从硝基苯衍生物中设计了一种新型的光诱导一氧化氮 (NO) 供体。使用 ESR 分析和 Griess 分析，在 4 位带有扩展 pi 电子系统的 2,6-二甲基硝基苯的可见光照射显示出有效的 NO 释放。计算研究和紫外光谱分析表明NO释放活性与硝基的构象、吸收强度和共轭π电子体系的长度密切相关。利用化合物 14 对 HCT116 人结肠癌细胞的光依赖性细胞毒性，证明 4-取代-2,6-二甲基硝基苯类似物是有用的 NO 供体，可用于时间和位点控制的 NO 治疗。
• Multiple bond-conjugated photoinduced nitric oxide releaser working with two-photon excitation
  作者：Kazuhiro Hishikawa、Hidehiko Nakagawa、Toshiaki Furuta、Kiyoshi Fukuhara、Hiroki Tsumoto、Takayoshi Suzuki、Naoki Miyata

  DOI：10.1016/j.bmcl.2009.10.120

  日期：2010.1

  Four novel nitric oxide (NO) releasers working via two-photon excitation (TPE), based on an acceptor-donor-acceptor (A-D-A) molecular design, were synthesized. Their decomposition and NO release in response to one-photon excitation, and their decomposition in response to two-photon excitation were examined. Their photoinduced decomposition characteristics are discussed. (c) 2009 Elsevier Ltd. All rights reserved.
• Hishikawa, Kazuhiro; Nakagawa, Hidehiko; Furuta, Toshiaki, Journal of the American Chemical Society, 2009, vol. 131, p. 7488 - 7489
  作者：Hishikawa, Kazuhiro、Nakagawa, Hidehiko、Furuta, Toshiaki、Fukuhara, Kiyoshi、Tsumoto, Hiroki、et al.

  DOI：——

  日期：——