2-(1,3-Dioxan-2-yl)-1-phenylethanon | 87971-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,3-Dioxan-2-yl)-1-phenylethanon
• 英文别名: 2-Benzoylmethyl-1,3-dioxane；2-(1',3'-dioxan-2'-yl)-1-phenylethanone；2-(1,3-Dioxan-2-yl)-1-phenylethanone
• CAS: 87971-35-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: RXXWEYADZVHGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-1-(1',3'-dioxan-2'-yl)-2-phenylethene 在 dirhodium tetraacetate 、 氢气 、 silica gel 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 100.0 ℃ 、3.45 MPa 条件下， 反应 24.0h， 生成 2-(1,3-Dioxan-2-yl)-1-phenylethanon
  参考文献：
  名称：

  Campi, Eva M.; Jackson, W. Roy; Perlmutter, Patrick, Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 995 - 1007

  摘要：

  DOI：

文献信息

• Catalysis of Pd(II)-Catalyzed Acetalization of Alkenes with Diols
  作者：Takahiro Hosokawa、Yoshiharu Ataka、Shun-Ichi Murahashi

  DOI：10.1246/bcsj.63.166

  日期：1990.1

  Alkenes bearing electron-withdrawing substituents are catalytically acetalized with 1,3-propanediol only by the use of PdCl2(MeCN)2 catalyst under O2 atmosphere. When a combination of BiCl3 and LiCl is used as co-catalyst, the acetalization proceeds effectively. These results indicate that a hydroperoxopalladium(II) species is most likely an active catalyst in the present reaction.

  具有吸电子取代基的烯烃在氧气气氛下仅使用PdCl2(MeCN)2催化剂催化与1,3-丙二醇进行缩醛化反应。当使用BiCl3和LiCl的组合作为共催化剂时，缩醛化反应有效进行。这些结果表明，氢过氧化钯(II)物种很可能是当前反应中的活性催化剂。
• Palladium(II)-catalysed acetalization of terminal olefins bearing electron-withdrawing substituents with 1,3- and 1,2-diols
  作者：Takahiro Hosokawa、Toshiyuki Ohta、Shun-Ichi Murahashi

  DOI：10.1039/c39830000848

  日期：——

  Treatment of terminal olefins bearing electron-withdrawing groups with (R,R)-pentane-2,4-diol (2) in the presence of PdCl2–CuCl–O2 in 1,2-dimethoxyethane gives cyclic acetals such as (3) and (12b)via attack at the terminal carbon atom; the corresponding acetals are similarly formed from propane-1,3-diol (5) and ethylene glycol (8).

  端烯烃轴承吸电子基团与（处理- [R ，- [R ）-戊烷-2,4-二醇（2在的PdCl存在下）2 -CuCl-O 2在1,2-二甲氧基乙烷给出环状缩醛，例如（3）和（12b）通过对末端碳原子的攻击；相应的缩醛类似地由丙烷1，3-二醇（5）和乙二醇（8）形成。
• Palladium(II)-catalyzed acetalization of terminal olefins bearing electron-withdrawing substituents with optically active diols
  作者：Takahiro Hosokawa、Toshiyuki Ohta、Satoshi Kanayama、Shunichi Murahashi

  DOI：10.1021/jo00385a021

  日期：1987.5
• Akguen, Eyuep; Pindur, Ulf, Liebigs Annalen der Chemie, 1985, # 12, p. 2472 - 2476
  作者：Akguen, Eyuep、Pindur, Ulf

  DOI：——

  日期：——
• Metal-free, PTSA catalyzed facile synthesis of β-ketoacetal from β-chlorocinnamaldehyde
  作者：Avinash K. Srivastava、Munsaf Ali、Kamal Nayan Sharma、Raj K. Joshi

  DOI：10.1016/j.tetlet.2018.07.022

  日期：2018.8

  A toluene solution of beta-chlorocinnamaldehyde and dihydroxy alcohols in the catalytic presence of paratoluenesulphonic acid (PTSA) yield the beta-ketoacetal in good to outstanding amount. The catalyst (PTSA), first selectively protect the aldehydic group to form the beta-chloroacetal and the subsequent dechlorination by H2O result the beta-ketoacetal. Significant transformation was achieved with electron donating substituent attached at the para-position of cinnamaldehyde. The selective formation of beta-keto-1,3-acetal was also obtained with a mixture of 1, 2- and 1, 3- diol. The present reaction consists of a metal-free, economical, robustly feasible, sizeable functional group tolerance and high yield properties. Moreover, the use of different dihydroxy alcohols made this process more benign and valuable towards the metal-free development of ketones. First, of its kind, a rare and unusual multitasking nature of PTSA is observed. (C) 2018 Elsevier Ltd. All rights reserved.