1-氯-1-氟-2-甲氧基-2-甲基环丙烷 | 144346-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-氯-1-氟-2-甲氧基-2-甲基环丙烷
• 英文名称: 1-chloro-1-fluoro-2-methoxy-2-methylcyclopropane
• 英文别名: 1-chloro-1-fluoro-2-methoxy-2-methyl-cyclopropane；1-chloro-1-fluoro-2-methoxy-2-methyl cyclopropane
• CAS: 144346-53-2
• 化学式: C₅H₈ClFO
• 分子量: 138.569
• InChiKey: YJQQSCPHFMBWFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氯-1-氟-2-甲氧基-2-甲基环丙烷 在 sodium dodecyl-sulfate 作用下， 生成 3-fluorobut-3-en-2-one
  参考文献：
  名称：

  烷氧基氯氟环丙烷的溶剂化开环：易于获得氟化的α，β-不饱和醛和酮†

  摘要：

  烷氧基氯氟环丙烷很容易通过在两相体系中将氯氟卡宾加成至醚中来制备，并通过在水性溶剂混合物中简单加热而转化为2-氟-2-烯基，该2-氟-2-烯基可以还原为相应的醇。

  DOI：

  10.1002/hlca.19770600528
• 作为产物：
  描述：

  2-甲氧基丙烯 在 18-冠醚-6 氢氧化钾 作用下， 以 aqueous KOH 、 二氯氟甲烷 、 水 为溶剂， 生成 1-氯-1-氟-2-甲氧基-2-甲基环丙烷
  参考文献：
  名称：

  Novel substituted aromatic compounds

  摘要：

  取代苯氧基、苯硫基和苯胺基化合物，其中间体，其合成以及它们用于控制害虫的用途。

  公开号：

  US04968829A1

文献信息

• Johnson, William S.; Buchanan, Robert A.; Bartlett, William R., Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 504 - 515
  作者：Johnson, William S.、Buchanan, Robert A.、Bartlett, William R.、Tham, Fook S.、Kullnig, Rudolph K.

  DOI：——

  日期：——
• The Fluorine Atom as a Cation-Stabilizing Auxiliary in Biomimetic Polyene Cyclizations:  Total Synthesis of <i>dl</i>-Dammarenediol¹
  作者：William S. Johnson、William R. Bartlett、Boris A. Czeskis、Arnaud Gautier、Cheol H. Lee、Rémy Lemoine、Eric J. Leopold、Gregory R. Luedtke、Katherine J. Bancroft

  DOI：10.1021/jo991196s

  日期：1999.12.1

  Dammarenediols I (1a) and II (1b) were prepared by an efficient nonenzymatic biomimetic polyene tetracyclization route. The cyclization substrate, pentaenol 3, contains a tetramethylallylic alcohol initiator, an allyltrimethylsilane terminating group, and a fluorine atom at pro-C-13 to serve as a cation-stabilizing (C-S) auxiliary controlling the regiochemistry of the C/D ring juncture. The synthesis of 3 employed lithium-halogen exchange to create alcohols 10 and 19. The Z-fluoroalkene in 3 was introduced stereoselectively via the Trost palladium-catalyzed alkylation of allylic acetate 11 (Z/E: 4.6/1). The cyclization of 3 was most efficient (62% isolated yield) when it was added as a dilute solution in dichloromethane to trifluoroacetic acid at -45 degrees C to afford tetracyclic fluoro diene 24 possessing the trans-anti-trans-anti-trans ring stereochemistry of the dammaranes. Replacement of the fluorine atom of 24 with hydrogen with complete retention of configuration was accomplished using the Ohsawa-Oishi reagent (Na/K alloy and crown ether). Wacker oxidation of the resulting hydrocarbon provided ketone 28, which after ketalization was ozonolyzed with a reductive workup to give the SP-alcohol 30. Ketal hydrolysis followed by Grignard reaction with isopentenylmagnesium bromide afforded the dammarenediols (1/3, 1a/1b).
• Johnson, William S.; Chenera, Balan; Tham, Fook S., Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 493 - 497
  作者：Johnson, William S.、Chenera, Balan、Tham, Fook S.、Kullnig, Rudolph K.

  DOI：——

  日期：——
• Acid-catalyzed conjugate additions to 3-fluorobutenone
  作者：Timothy B. Patrick、Upendra P. Dahal

  DOI：10.1016/j.jfluchem.2009.02.007

  日期：2009.5

  3-Fluorobutenone (2) reacts under Zn(II) catalysis in ethanol solution with active methylene compounds such as anthrone and aromatic phenols to give products of the addition of one unit of 3-fluorobutenone. (C) 2009 Elsevier B.V. All rights reserved.
• Microwave assisted Diels-Alder cycloaddition of 2-fluoro-3-methoxy-1,3-butadiene
  作者：Timothy B. Patrick、Keith Gorrell、James Rogers

  DOI：10.1016/j.jfluchem.2007.03.010

  日期：2007.7

  The title fluorodiene (2) reacts with several dienophiles in moderate yields (20-65%, 0.5 h to 3d) when thermal activation is used. When 100 W microwave radiation is used the reaction yields (70-90%, 5-25 min) are greatly improved and the reaction times are much shorter. A microwave procedure is also used for the hydrolysis of vinyl ether cycloadducts to alpha-fluoroketones. (c) 2007 Elsevier B.V. All rights reserved.