6-氟戊酸 | 2822-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 6-氟戊酸
• 英文名称: 6-fluoromevalonate
• 英文别名: 4-(fluoromethyl)-4-hydroxyoxan-2-one
• CAS: 2822-77-7
• 化学式: C₆H₉FO₃
• 分子量: 148.134
• InChiKey: DPPMVKMESJJAJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  307.8±22.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥3 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-氟戊酸 生成 (S)-(+)-fluoromevalonolactone
  参考文献：
  名称：

  KOPPENHOEFER, B.;ALLMENDINGER, H.;NICHOLSON, G., ANGEW. CHEM., 1985, 97, N 1, 46-48

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Hydroxy-3-fluormethyl-glutarsaeure 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.5h， 生成 6-氟戊酸
  参考文献：
  名称：

  Shuto, Akira; Kuwano, Eiichi; Eto, Morifusa, Agricultural and Biological Chemistry, 1988, vol. 52, # 4, p. 915 - 920

  摘要：

  DOI：

文献信息

• Synthesis of mevalonate- and fluorinated mevalonate prodrugs and their in vitro human plasma stability
  作者：Soosung Kang、Mizuki Watanabe、J.C. Jacobs、Masaya Yamaguchi、Samira Dahesh、Victor Nizet、Thomas S. Leyh、Richard B. Silverman

  DOI：10.1016/j.ejmech.2014.11.040

  日期：2015.1

  The mevalonate pathway is essential for the production of many important molecules in lipid biosynthesis. Inhibition of this pathway is the mechanism of statin cholesterol-lowering drugs, as well as the target of drugs to treat osteoporosis, to combat parasites, and to inhibit tumor cell growth. Unlike the human mevalonate pathway, the bacterial pathway appears to be regulated by diphosphomevalonate (DPM). Enzymes in the mevalonate pathway act to produce isopentenyl diphosphate, the product of the DPM decarboxylase reaction, utilize phosphorylated (charged) intermediates, which are poorly bioavailable. It has been shown that fluorinated DPMs (6-fluoro- and 6,6,6-trifluoro-5diphosphomevalonate) are excellent inhibitors of the bacterial pathway; however, highly charged DPM and analogs are not bioavailable. To increase cellular permeability of mevalonate analogs, we have synthesized various prodrugs of mevalonate and 6-fluoro- and 6,6,6-trifluoromevalonate that can be enzymatically transformed to the corresponding DPM or fluorinated DPM analogs by esterases or amidases. To probe the required stabilities as potentially bioavailable prodrugs, we measured the half-lives of esters, amides, carbonates, acetals, and ketal promoieties of mevalonate and the fluorinated mevalonate analogs in human blood plasma. Stability studies showed that the prodrugs are converted to the mevalonates in human plasma with a wide range of half-lives. These studies provide stability data for a variety of prodrug options having varying stabilities and should be very useful in the design of appropriate prodrugs of mevalonate and fluorinated mevalonates. (C) 2014 Elsevier Masson SAS. All rights reserved.
• SHUTO, AKIRA;KUWANO, EIICHI;ETO, MORIFUSA, AGR. AND BIOL. CHEM., 52,(1988) N 4, 915-919
  作者：SHUTO, AKIRA、KUWANO, EIICHI、ETO, MORIFUSA

  DOI：——

  日期：——
• Shuto, Akira; Kuwano, Eiichi; Eto, Morifusa, Agricultural and Biological Chemistry, 1988, vol. 52, # 4, p. 915 - 920
  作者：Shuto, Akira、Kuwano, Eiichi、Eto, Morifusa

  DOI：——

  日期：——
• KOPPENHOEFER, B.;ALLMENDINGER, H.;NICHOLSON, G., ANGEW. CHEM., 1985, 97, N 1, 46-48
  作者：KOPPENHOEFER, B.、ALLMENDINGER, H.、NICHOLSON, G.

  DOI：——

  日期：——