(S)-1-(2,3-difluro-6-nitrophenoxy)propan-2-yl methanesulfonate | 129798-16-9

• 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: (S)-1-(2,3-difluro-6-nitrophenoxy)propan-2-yl methanesulfonate
• 英文别名: [(2S)-1-(2,3-difluoro-6-nitrophenoxy)propan-2-yl] methanesulfonate
• CAS: 129798-16-9
• 化学式: C₁₀H₁₁F₂NO₆S
• 分子量: 311.263
• InChiKey: YRSYYTPQJGHWEN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-1-(2,3-difluro-6-nitrophenoxy)propan-2-yl methanesulfonate 、 苯甲酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以95%的产率得到(R)-1-(2,3-difluro-6-nitrophenoxy)propan-2-yl benzoate
  参考文献：
  名称：

  Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH

  摘要：

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.028
• 作为产物：
  描述：

  甲基磺酰氯 、 2,3-Difluoro-6-nitro-{[(S)-2-hydroxypropyl]oxy}benzene 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以87%的产率得到(S)-1-(2,3-difluro-6-nitrophenoxy)propan-2-yl methanesulfonate
  参考文献：
  名称：

  Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH

  摘要：

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.028

文献信息

• Optically active benzoxazines and bezothiazines and a process for their stereospecific preparation
  申请人：GIST-BROCADES N.V.

  公开号：EP0368410A2

  公开（公告）日：1990-05-16

  Optically active 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazines and 7,8-difluoro-3,4-dihydro-2-methyl-2H-[1,4]benzoxazines and the corresponding benzothiazines of formula III, where, one of the substituents R1, R2, R3 and R4 is CH20H or -CH2Z, the remaining being hydrogen, X denotes fluoro, chloro, methyl or hydrogen, Y is oxygen or sulfur and Z is hydrogen, fluoro or protected hydroxyl are obtained as the stereochemically pure products of a stereospecific synthesis using a 3,4-difluoronitrobenzene substituted with a stereochemically pure 2-(1-hydroxyisopropoxy), 2-(2-hydrox-I ypropoxy), 2-(1-hydroxyisopropylthio) or 2-(2-hydroxypropylthio) substituent. The obtained compounds are suited for the production of optically active pyridobenzoxazines and pyridobenzothiazines, among which are useful antibacterial optically active quinolones, particularly (S)-(-)-ofloxacin.

  具有光学活性的 7,8-二氟-3,4-二氢-3-甲基-2H-[1,4]苯并噁嗪和 7,8-二氟-3,4-二氢-2-甲基-2H-[1,4]苯并噁嗪以及相应的式 III 的苯并噻嗪、 其中，取代基 R1、R2、R3 和 R4 之一为 CH20H 或 -CH2Z，其余为氢；X 表示氟、氯、甲基或氢；Y 表示氧或硫，Z 表示氢、在使用立体化学纯度为 2-（1-羟基异丙氧基）、2-（2-羟基-I y 丙氧基）、2-（1-羟基异丙硫基）或 2-（2-羟基丙硫基）取代基取代的 3,4-二氟硝基苯进行立体特异性合成时，可获得氟或受保护羟基的立体化学纯度为 3,4-二氟硝基苯的产物。 所得到的化合物适用于生产光学活性吡啶并噁嗪类和吡啶并噻嗪类化合物，其中包括有用的抗菌光学活性喹诺酮类化合物，特别是 (S)-(-)-ofloxacin 。
• Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH
  作者：Xiao-Xin Shi、Chun-Li Shen、Jian-Zhong Yao、Liang-Deng Nie、Na Quan

  DOI：10.1016/j.tetasy.2009.12.028

  日期：2010.3

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.