7-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 7-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 7-Fluoro-2-methyl-1,2,3,4-tetrahydronaphthalen-1-one；7-fluoro-2-methyl-3,4-dihydro-2H-naphthalen-1-one
• 化学式: C₁₁H₁₁FO
• 分子量: 178.206
• InChiKey: BLVCCKNVRDAYLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one 在 C₄₈H₃₈I₄O₇ 、 cesium fluoride 、 (R)-3,3'-diiodo-[1,1'-binaphthalene]-2,2'-diol 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 (2S)-7-fluoro-2-methyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  自组装手性笼中的氟阴离子用于甲硅烷基烯醇醚的对映选择性质子化

  摘要：

  Song的手性低聚乙二醇（oligoEGs）作为催化剂的潜力已在三甲基甲硅烷基烯醇醚与碱金属氟化物（KF和CsF）结合以及质子源存在下的对映选择性质子化中得到了探索。获得了α-取代的四氢萘酮的各种甲硅烷基烯醇醚的高度对映选择性质子化，以完全转化并具有高达99％的ee产生了手性α-取代的四氢萘酮。已建立的协议已成功扩展到生物相关的手性α-取代的苯并二氢吡喃酮和硫代苯并二氢吡喃酮衍生物的合成。

  DOI：

  10.1021/acs.orglett.7b01429
• 作为产物：
  描述：

  7-氟-1-四氢萘酮 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以64%的产率得到7-fluoro-2-methyl-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones

  摘要：

  Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of lessacidic pro-nucleophiles. The newly developed bis(guanidino)iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.

  DOI：

  10.1021/ja408296h

文献信息

• Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones
  作者：Tadahiro Takeda、Masahiro Terada

  DOI：10.1021/ja408296h

  日期：2013.10.16

  Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of lessacidic pro-nucleophiles. The newly developed bis(guanidino)iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.
• Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
  作者：Sushovan Paladhi、Yidong Liu、B. Senthil Kumar、Min-Jung Jung、Sang Yeon Park、Hailong Yan、Choong Eui Song

  DOI：10.1021/acs.orglett.7b01429

  日期：2017.6.16

  The potential of Song’s chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones

  Song的手性低聚乙二醇（oligoEGs）作为催化剂的潜力已在三甲基甲硅烷基烯醇醚与碱金属氟化物（KF和CsF）结合以及质子源存在下的对映选择性质子化中得到了探索。获得了α-取代的四氢萘酮的各种甲硅烷基烯醇醚的高度对映选择性质子化，以完全转化并具有高达99％的ee产生了手性α-取代的四氢萘酮。已建立的协议已成功扩展到生物相关的手性α-取代的苯并二氢吡喃酮和硫代苯并二氢吡喃酮衍生物的合成。