2-羟基-2-丙-2-烯基-3,4-二氢萘-1-酮 | 221681-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-羟基-2-丙-2-烯基-3,4-二氢萘-1-酮
• 英文名称: 2-allyl-3,4-dihydro-2-hydroxynaphthalen-1(2H)-one
• 英文别名: 1(2H)-Naphthalenone, 3,4-dihydro-2-hydroxy-2-(2-propenyl)-；2-hydroxy-2-prop-2-enyl-3,4-dihydronaphthalen-1-one
• CAS: 221681-02-3
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: WCIGURCXSXMKBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟基-2-丙-2-烯基-3,4-二氢萘-1-酮 在 sodium hydroxide 、 三氟甲磺酸酐 、 盐酸羟胺 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 98.5h， 生成
  参考文献：
  名称：

  Fragmentation of Nitrone Triflates to 9-Membered Rings

  摘要：

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

  DOI：

  10.1021/ol071049d
• 作为产物：
  描述：

  Tetralone N,N-dimethylhydrazone 在 盐酸 、 双(三甲基硅烷基)氨基钾 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 55.0h， 生成 2-羟基-2-丙-2-烯基-3,4-二氢萘-1-酮
  参考文献：
  名称：

  Fragmentation of Nitrone Triflates to 9-Membered Rings

  摘要：

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

  DOI：

  10.1021/ol071049d

文献信息

• Catalytic Synthesis of α-Hydroxy Ketones Using Organic–Inorganic Hybrid Polymer
  作者：Takayoshi Arai、Hitomi Takasugi、Toru Sato、Hiroshi Noguchi、Hirofumi Kanoh、Katsumi Kaneko、Akira Yanagisawa

  DOI：10.1246/cl.2005.1590

  日期：2005.12

  Oxidation of silyl enolates was found to be smoothly catalyzed by [Cu(bpy)(BF4)2(H2O)2(bpy)]n (bpy = 4,4′-bipyridine) under molecular oxygen, and provided the corresponding α-hydroxy carbonyl compounds in high yield. The insoluble organic–inorganic hybrid polymer was readily recovered by centrifugation after the completion of reaction, and the recovered catalyst could be reused.

  发现硅烯醇盐的氧化反应在分子氧的催化作用下，由[Cu(bpy)(BF4)2(H2O)2(bpy)]n（bpy = 4,4′-联吡啶）顺利进行，并获得了高产率的相应α-羟基羰基化合物。反应完成后，不溶性的有机-无机杂化聚合物可以通过离心轻松回收，回收的催化剂可以重复使用。
• Organic–Inorganic Hybrid Polymer-Encapsulated Magnetic Nanobead Catalysts
  作者：Takayoshi Arai、Toru Sato、Hirofumi Kanoh、Katsumi Kaneko、Koichi Oguma、Akira Yanagisawa

  DOI：10.1002/chem.200701371

  日期：2008.1.18

  strategy for the encapsulation of magnetic nanobeads was developed by using the in situ self-assembly of an organic-inorganic hybrid polymer. The hybrid polymer of [Cu(bpy)(BF(4))(2)(H(2)O)(2)](bpy)}(n) (bpy=4,4'-bipyridine) was constructed on the surface of amino-functionalized magnetic beads and the resulting hybrid-polymer-encapsulated beads were utilized as catalysts for the oxidation of silyl enolates

  通过使用有机-无机杂化聚合物的原位自组装，开发了一种磁性纳米珠囊化的新策略。构造了[Cu（bpy）（BF（4））（2）（H（2）O）（2）]（bpy）}（n）（bpy = 4,4'-联吡啶）的杂化聚合物氨基官能化磁珠的表面和所得的杂化聚合物包封的珠用作氧化甲硅烷基化物的催化剂，从而以高收率提供相应的α-羟基羰基化合物。反应完成后，通过磁分离容易地回收催化剂，并且回收的催化剂可以重复使用几次。由于当前的方法不需要复杂的过程即可将催化剂掺入磁珠中，
• Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution
  作者：Mei Kee Kam、Akira Sugiyama、Ryouta Kawanishi、Kazutaka Shibatomi

  DOI：10.3390/molecules25173902

  日期：——

  were synthesized with high enantiopurity by asymmetric decarboxylative chlorination and subsequent nucleophilic substitution. We recently reported the asymmetric decarboxylative chlorination of β-ketocarboxylic acids in the presence of a chiral primary amine catalyst to obtain α-chloroketones with high enantiopurity. Here, we found that nucleophilic substitution of the resulting α-chloroketones with tetrabutylammonium

  通过不对称脱羧氯化和随后的亲核取代合成了具有高对映纯度的手性叔α-羟基酮。我们最近报道了在手性伯胺催化剂存在下 β-酮羧酸的不对称脱羧氯化，以获得具有高对映纯度的 α-氯酮。在这里，我们发现用四丁基氢氧化铵对所得 α-氯酮进行亲核取代产生相应的 α-羟基酮，而不会损失对映纯度。即使在叔碳下反应也能顺利进行。所提出的方法可用于制备手性叔醇。
• Lewis Base-Catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Carbonyl Compounds
  作者：Yoshinori Sato、Hidehiko Fujisawa、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.1275

  日期：2006.8

  Lewis base-catalyzed [2,3]-Wittig rearrangement of silyl enolates generated from α-allyloxy carbonyl compounds is described. The [2,3]-Wittig rearrangement of silyl enolates generated from α-allylo...

  描述了路易斯碱催化的 [2,3]-Wittig 重排由 α-烯丙氧基羰基化合物产生的甲硅烷基烯醇化物。α-烯丙基生成的甲硅烷基烯醇化物的 [2,3]-Wittig 重排...
• Lewis Base-catalyzed [2,3]-Wittig Rearrangement of Silyl Enolates Generated from α-Allyloxy Ketones
  作者：Yoshinori Sato、Hidehiko Fujisawa、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.588

  日期：2005.4

  Silyl enolates generated from α-allyloxy ketones afforded the [2,3]-Wittig rearrangement products in good to high yields in the presence of a catalytic amount of Lewis base such as lithium 2-pyrrol...

  在催化量的路易斯碱（如 2-吡咯锂）存在下，由 α-烯丙氧基酮生成的甲硅烷基烯醇化物以良好至高产率提供 [2,3]-Wittig 重排产物。