6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one | 195376-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• 英文别名: 4H-1,3-Dioxin-4-one, 6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-；6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-1,3-dioxin-4-one
• CAS: 195376-03-5
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: AITQGGQCRKDQQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 在 吡啶 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 、 苯 为溶剂， 生成 (4aS,5aR,8S,9aR)-2,2-Dimethyl-8-phenethyl-hexahydro-1,3,7-trioxa-cyclobuta[1,2:1,4]dibenzen-4-one
  参考文献：
  名称：

  取代的四氢呋喃酮和四氢吡喃酮的合成：二恶英酮的光环加成/片段化反应

  摘要：

  二恶英酮羟醛加成方法和[2 + 2]-光环加成/片段化反应的结合可以提供取代的四氢呋喃-3-酮和四氢吡喃-4-酮，它们是在生物活性天然产物中大量存在的亚基。乙烯基和烯丙基醚与二恶英酮的分子内光环化，然后在碱性MeOH（K 2 CO 3）中裂解，可生成四氢呋喃-3-酮和四氢吡喃-4-酮，从而为复杂分子合成的通用组成部分提供了一条实用途径。

  DOI：

  10.1016/s0040-4039(97)01262-8
• 作为产物：
  描述：

  (2,2-dimethyl-6-methylene-6H-1,3-dioxin-4-yloxy)trimethylsilane 在 苯甲酸 三氟乙酸 作用下， 反应 24.0h， 生成 6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
  参考文献：
  名称：

  Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid

  摘要：

  The vinylogous aldol reaction of O-silyl dienolates deriving from 2,2-dimethyl-[1,3]-dioxin-4-ones proceeds in moderate to excellent yields in the presence of catalytic amounts of PhCOOH under solvent-free conditions. Modest to good yields can be obtained by using silica gel or 3 A molecular sieves as heterogeneous catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.152

文献信息

• Stereoselective Synthesis of Tetrahydropyran-4-ones from Dioxinones Catalyzed by Scandium(III) Triflate
  作者：William J. Morris、Daniel W. Custar、Karl A. Scheidt

  DOI：10.1021/ol050093v

  日期：2005.3.1

  [reaction: see text] A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and beta-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in

  [反应：见正文]已发现三氟甲磺酸scan催化醛与β-羟基二恶英酮之间的非对映选择性环化。该过程利用了二恶英酮核心中嵌入的烯醇醚的未开发的亲核性。可以从所得环化反应中分离出双环化合物，或者可以直接添加醇盐亲核试剂。该原位加成使二恶英酮环断裂，并以高收率和高非对映选择性递送3-羧基取代的四氢吡喃-4-酮。
• Versatile Asymmetric Synthesis of the Kavalactones:  First Synthesis of (+)-Kavain
  作者：Thomas E. Smith、Mabel Djang、Alan J. Velander、C. Wade Downey、Kathleen A. Carroll、Sophie van Alphen

  DOI：10.1021/ol0493960

  日期：2004.7.1

  Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.
• Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases
  作者：Arrigo Scettri、Vincenzo De Sio、Rosaria Villano、Patrizia Manzo、Maria Rosaria Acocella

  DOI：10.1016/j.tetlet.2010.05.016

  日期：2010.7

  The vinylogous aldol-type addition of a dienolsilyl ether, derived from 2,2,6-trimethyl-4H-1,3-dioxin-4-one, showed to occur with complete gamma-selectivity by enolate activation promoted by neutral Lewis bases under solvent-free conditions. Moderate to high yields were obtained with aromatic, hetero-aromatic, and aliphatic aldehydes, as well as activated ketones. Under the same conditions and in the absence of catalyst, the first Mukaiyama-Michael addition of the masked acetoacetate ester to alpha,beta-unsaturated aldehydes took place in satisfactory way. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Brønsted Acid Catalyzed Synthesis of Spirooxindole Pyrans
  作者：Jingqi Wang、Erika A. Crane、Karl A. Scheidt

  DOI：10.1021/ol200987c

  日期：2011.6.17

  A Bronsted acid-catalyzed Prins-type cyclization sequence to construct spirooxindole pyrans in high yields and excellent diastereoselectivity has been developed. The combination of a beta-hydroxy dioxinone fragment and isatin dimethyl acetal generate oxa-spirooxindoles efficiently. These compounds are diversifiable scaffolds that tap into the rich chemistry of dioxinones.
• Solvent-free Mukaiyama aldol reaction of O-silyl dienolates catalyzed by benzoic acid
  作者：Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetlet.2005.06.152

  日期：2005.9

  The vinylogous aldol reaction of O-silyl dienolates deriving from 2,2-dimethyl-[1,3]-dioxin-4-ones proceeds in moderate to excellent yields in the presence of catalytic amounts of PhCOOH under solvent-free conditions. Modest to good yields can be obtained by using silica gel or 3 A molecular sieves as heterogeneous catalysts. (c) 2005 Elsevier Ltd. All rights reserved.