(S)-1-fluoro-2-propanol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (S)-1-fluoro-2-propanol
• 英文别名: (2S)-1-fluoropropan-2-ol
• 化学式: C₃H₇FO
• 分子量: 78.0864
• InChiKey: WPUWNCWLDZMYSC-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-fluoro-2-propanol 、 5-Fluoro-4-(2-methyl-6-methylsulfonylpyridin-3-yl)oxy-6-piperidin-4-yloxypyrimidine 、 N,N'-羰基二咪唑 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [(2S)-1-fluoropropan-2-yl] 4-[5-fluoro-6-(2-methyl-6-methylsulfonylpyridin-3-yl)oxypyrimidin-4-yl]oxypiperidine-1-carboxylate
  参考文献：
  名称：

  Discovery and optimization of 5-fluoro-4,6-dialkoxypyrimidine GPR119 agonists

  摘要：

  A series of 5-fluoro-4,6-dialkoxypyrimidine GPR119 modulators were discovered and optimized for in vitro agonist activity. A lead molecule was identified that has improved agonist efficacy relative to our clinical compound (APD597) and possesses reduced CYP2C9 inhibitory potential. This optimized lead was found to be efficacious in rodent models of glucose control both alone and in combination with a Dipeptidyl peptidase-4 (DPP-4) inhibitor.

  DOI：

  10.1016/j.bmcl.2014.06.071
• 作为产物：
  描述：

  氟代丙酮 在 (-)-diisopinocamphenylborane chloride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (S)-1-fluoro-2-propanol 、 (R)-1-fluoro-2-propanol
  参考文献：
  名称：

  氟对氟甲基酮不对称还原的影响

  摘要：

  使用（-）-二异樟脑基氯硼烷[（-）-DIP-Chloride™]和（-）- B-异樟脑基-9-borabicyclo [ ]不对称还原代表性的芳基和烷基α-氟代和α-氯甲基酮的比较研究3.3.1]壬烷[ ř -Alpine -硼烷® ]已经取得进展。观察到，对于两种类型的卤代酮，DIP-Chloride™在速率和对映选择性方面均优越。用DIP-Chloride™还原一氟丙酮和三氟丙酮可分别提供61％ee和96％ee的产物醇，而二氟丙酮的还原仅可产生5％ee。对于一氯丙酮，未观察到孤卤原子的影响，所有这些都表明一氟丙酮对路易斯酸性氯硼烷的螯合作用。

  DOI：

  10.1016/j.jfluchem.2007.04.015

文献信息

• BRAVO, PIERFRANCESCO;PIOVOSI, ELENA;RESNATI, GUISEPPE, J. CHEM. RES. (S),(1989) N, C. 134-135
  作者：BRAVO, PIERFRANCESCO、PIOVOSI, ELENA、RESNATI, GUISEPPE

  DOI：——

  日期：——
• Discovery and optimization of 5-fluoro-4,6-dialkoxypyrimidine GPR119 agonists
  作者：Daniel J. Buzard、Sun Hee Kim、Juerg Lehmann、Sangdon Han、Imelda Calderon、Amy Wong、Andrew Kawasaki、Sanju Narayanan、Rohit Bhat、Tawfik Gharbaoui、Luis Lopez、Dawei Yue、Kevin Whelan、Hussien Al-Shamma、David J. Unett、Hsin-Hui Shu、Shiu-Feng Tung、Steve Chang、Ching-Fen Chuang、Michael Morgan、Abu Sadeque、Zhi-Liang Chu、James N. Leonard、Robert M. Jones

  DOI：10.1016/j.bmcl.2014.06.071

  日期：2014.9

  A series of 5-fluoro-4,6-dialkoxypyrimidine GPR119 modulators were discovered and optimized for in vitro agonist activity. A lead molecule was identified that has improved agonist efficacy relative to our clinical compound (APD597) and possesses reduced CYP2C9 inhibitory potential. This optimized lead was found to be efficacious in rodent models of glucose control both alone and in combination with a Dipeptidyl peptidase-4 (DPP-4) inhibitor.
• The influence of fluorine on the asymmetric reduction of fluoromethyl ketones
  作者：P. Veeraraghavan Ramachandran、Baoqing Gong、Aleksandar V. Teodorović

  DOI：10.1016/j.jfluchem.2007.04.015

  日期：2007.7

  study of the asymmetric reduction of representative aryl and alkyl α-fluoro- and α-chloromethyl ketones using (−)-diisopinocampheylchloroborane [(−)-DIP-Chloride™] and (−)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane [R-Alpine-Borane®] has been made. It was observed that DIP-Chloride™ is superior in terms of the rate and enantioselectivity for both classes of halo-ketones. While the reduction of monofluoroacetone

  使用（-）-二异樟脑基氯硼烷[（-）-DIP-Chloride™]和（-）- B-异樟脑基-9-borabicyclo [ ]不对称还原代表性的芳基和烷基α-氟代和α-氯甲基酮的比较研究3.3.1]壬烷[ ř -Alpine -硼烷® ]已经取得进展。观察到，对于两种类型的卤代酮，DIP-Chloride™在速率和对映选择性方面均优越。用DIP-Chloride™还原一氟丙酮和三氟丙酮可分别提供61％ee和96％ee的产物醇，而二氟丙酮的还原仅可产生5％ee。对于一氯丙酮，未观察到孤卤原子的影响，所有这些都表明一氟丙酮对路易斯酸性氯硼烷的螯合作用。