(+/-)-3-fluoro-2-hydroxy-2-methylpropanenitrile | 2925-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-fluoro-2-hydroxy-2-methylpropanenitrile
• 英文别名: 3-fluoro-2-hydroxy-2-methylpropanenitrile；fluoro-DMK cyanohydrin；β-fluoro-α-hydroxy-isobutyronitrile；β-Fluor-α-hydroxy-isobutyronitril；3-Fluor-2-hydroxy-2-methyl-propionitril；Fluoraceton-cyanhydrin；3-Fluoro-2-hydroxy-2-methylpropanenitrile
• CAS: 2925-95-3
• 化学式: C₄H₆FNO
• 分子量: 103.096
• InChiKey: USTQBHSSNOJGMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-fluoro-2-hydroxy-2-methylpropanenitrile 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 以0.08 g的产率得到(+/-)-3-fluoro-2-hydroxy-2-methylpropanoic acid
  参考文献：
  名称：

  [EN] COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS
  [FR] ASSOCIATIONS D'INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组合物，以及抑制NS5A蛋白功能的方法。

  公开号：

  WO2015005901A1
• 作为产物：
  描述：

  sodium cyanide 、 氟代丙酮 以 乙醚 、 水 为溶剂， 反应 18.0h， 以0.56 g的产率得到(+/-)-3-fluoro-2-hydroxy-2-methylpropanenitrile
  参考文献：
  名称：

  [EN] COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS
  [FR] ASSOCIATIONS D'INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组合物，以及抑制NS5A蛋白功能的方法。

  公开号：

  WO2015005901A1

文献信息

• Naturally occurring cyanohydrins, analogues and derivatives as potential insecticides
  作者：Chris J Peterson、Rong Tsao、Joel R Coats

  DOI：10.1002/1526-4998(200007)56:7<615::aid-ps173>3.0.co;2-w

  日期：2000.7

  Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos

  测试了几种天然存在的氰醇对两种昆虫物种的熏蒸毒性，即家蝇 (Musca domestica L) 和较小的谷物螟 (Rhyzopertha dominica (F))。还测试了这些化合物的合成类似物。大多数测试的氰醇作为熏蒸剂对家蝇和多米尼卡的毒性比氯化苦更大；有些化合物的毒性几乎与敌敌畏一样。天然存在的氰醇是测试中毒性最强的。
• Recherches sur la formation et la transformation des esters XXXII. Sur la préparation de quelques nouveaux monoesters cyanoalcoyl-phosphoriques et sur leur vitesse de scission à différents pH
  作者：Emile Cherbuliez、H. Probst、J. Rabinowitz

  DOI：10.1002/hlca.19620450340

  日期：——

  The synthesis and the rate of scission of some new cyanoalkyl-phosphoric monoesters are described. In the case of β-cyanoalkyl-phosphoric monoesters, the monoester group is no more dephosphorylated in alkaline medium when the two H in the β position are substituted by alkyl groups.

  描述了一些新的氰基烷基磷酸单酯的合成及其断裂速率。在β-氰基烷基-磷酸单酯的情况下，当在β位置上的两个H被烷基取代时，在碱性介质中单酯基团不再被去磷酸化。
• Recherches sur la formation et la transformation de dérivés organiques du fluor III. Préparation d'hydroxy-acides, d'hydroxy-nitriles, d'hydroxy-esters et d'hydroxy-éthers fluorés ainsi que de leurs dérivé phosphorylés
  作者：Emile Cherbuliez、A. de Picciotto、J. Rabinowitz

  DOI：10.1002/hlca.19600430426

  日期：——

  Some new fluorinated hydroxy-acids and hydroxy-ethers as well as their phosphorylated derivatives are described.

  描述了一些新的氟化羟基酸和羟基醚以及它们的磷酸化衍生物。
• Voong; Chiang, Huaxue Xuebao/Acta Chimica Sinica, 1958, vol. 24, p. 155,157
  作者：Voong、Chiang

  DOI：——

  日期：——
• Prostate cancer PET bioprobes: Synthesis of [18F]-radiolabeled hydroxyflutamide derivatives
  作者：Orit Jacobson、Yossi Bechor、Avi Icar、Nurit Novak、Atalia Birman、Hanit Marom、Ludmila Fadeeva、Elizabeth Golan、Ilan Leibovitch、Mordechai Gutman、Einat Even-Sapir、Roland Chisin、Michael Gozin、Eyal Mishani

  DOI：10.1016/j.bmc.2005.06.033

  日期：2005.11

  Approximately 80-90% of prostate cancers are androgen dependent at initial diagnosis. The androgen receptor (AR) is present in most advanced prostate cancer specimens and is believed to have a critical role in its development. Today, treatment of prostate cancer is done by inhibition of AR using antiandrogens such as flutamide (pro-drug of hydroxyflutamide), nilutamide, and bicalutamide. However, there is currently no noninvasive imaging modalities to detect, guide, and monitor specific treatment of AR-positive prostate cancer. (R)-3-Bromo-N-(4-fluoro-3-(trifluoromethy, phenyl)-2-hydroxy-2-methyl-propanamide [F-18]-1 and N-(4fluoro-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide [F-18]-2, derivatives of hydroxyflutamide, were synthesized as a fluorine-containing imaging agent candidates. A three-step fluorine-18 radiosynthesis route was developed, and the compounds were successfully labeled with a 10 +/- 3% decay corrected radiochemical yield, 95% radiochemical purity, and a specific activity of 1500 +/- 200 Ci/mmol end of bombardment (n = 10). These labeled biprobes not only may enable for the future quantitative molecular imaging of AR-positive prostate cancer using positron emission tomography but may also allow for image-guided treatment of prostate cancer. (c) 2005 Elsevier Ltd. All rights reserved.