5-Iodo-2,2-dimethyl-6-phenyl-1,3-dioxin-4-one | 142779-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Iodo-2,2-dimethyl-6-phenyl-1,3-dioxin-4-one
• 英文别名: 2,2-dimethyl-5-iodo-6-phenyl-1,3-dioxin-4-one
• CAS: 142779-84-8
• 化学式: C₁₂H₁₁IO₃
• 分子量: 330.122
• InChiKey: FRGKDSWTHBGCAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Iodo-2,2-dimethyl-6-phenyl-1,3-dioxin-4-one 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2,2-dimethyl-4-oxo-6-phenyl-4H-1,3-dioxin-5-yl)magnesium chloride
  参考文献：
  名称：

  New functionalized alkenylmagnesium reagents bearing an oxygen function in the β-position. Preparation and reaction of 5-magnesiated-1,3-dioxin-4-one derivatives

  摘要：

  5-Magnesiated-1,3-dioxin-4-ones have been prepared by performing a low temperature iodine-magnesium exchange reaction. These alkenylmagnesium reagents bearing an alkoxy function in the beta -position react directly with aldehydes or with other electrophiles such as acid chlorides, allylic bromides, aryl and alkenyl iodides in the presence of a copper or palladium transition metal catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01426-5
• 作为产物：
  描述：

  6-phenyl-2,2-dimethyl-1,3-dioxin-4-one 在 N-碘代丁二酰亚胺 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 以85%的产率得到5-Iodo-2,2-dimethyl-6-phenyl-1,3-dioxin-4-one
  参考文献：
  名称：

  New functionalized alkenylmagnesium reagents bearing an oxygen function in the β-position. Preparation and reaction of 5-magnesiated-1,3-dioxin-4-one derivatives

  摘要：

  5-Magnesiated-1,3-dioxin-4-ones have been prepared by performing a low temperature iodine-magnesium exchange reaction. These alkenylmagnesium reagents bearing an alkoxy function in the beta -position react directly with aldehydes or with other electrophiles such as acid chlorides, allylic bromides, aryl and alkenyl iodides in the presence of a copper or palladium transition metal catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01426-5

文献信息

• Preparation of α-functionalized alkenylmagnesium reagents via a halide–magnesium exchange
  作者：Jérôme Thibonnet、Viet Anh Vu、Laurent Bérillon、Paul Knochel

  DOI：10.1016/s0040-4020(02)00439-8

  日期：2002.6

  A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the alpha-position (Y=CN, CO2R, CONR2, SO2Ph) has been made possible by using a low temperature (-40 to -30degreesC) bromine-magnesium exchange with i-PrMgBr in THF. This reaction has also been used to prepare 5-magnesiated-1,3-dioxin-4-one derivatives bearing an alkoxy substituent in beta-position to the carbon-magnesium bond. (C) 2002 Published by Elsevier Science Ltd.
• Iwaoka, Tomoyasu; Murohashi, Tomoko; Katagiri, Nobuya, Journal of the Chemical Society. Perkin transactions I, 1992, # 11, p. 1393 - 1398
  作者：Iwaoka, Tomoyasu、Murohashi, Tomoko、Katagiri, Nobuya、Sato, Masayuki、Kaneko, Chikara

  DOI：——

  日期：——
• New functionalized alkenylmagnesium reagents bearing an oxygen function in the β-position. Preparation and reaction of 5-magnesiated-1,3-dioxin-4-one derivatives
  作者：Viet Anh Vu、Laurent Bérillon、Paul Knochel

  DOI：10.1016/s0040-4039(01)01426-5

  日期：2001.9

  5-Magnesiated-1,3-dioxin-4-ones have been prepared by performing a low temperature iodine-magnesium exchange reaction. These alkenylmagnesium reagents bearing an alkoxy function in the beta -position react directly with aldehydes or with other electrophiles such as acid chlorides, allylic bromides, aryl and alkenyl iodides in the presence of a copper or palladium transition metal catalyst. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Highly efficient palladium-catalyzed Suzuki–Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to α-aryl-β-ketoesters
  作者：Adriano S. Vieira、Rodrigo L.O.R. Cunha、Clécio F. Klitzke、Julio Zukerman-Schpector、Hélio A. Stefani

  DOI：10.1016/j.tet.2009.11.027

  日期：2010.1

  The high efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates 3 with 5-iodo-1,3-dioxin-4-ones 2a-b in water as only solvent in the presence of n-Bu4NOH as base is reported. The respective 5-aryl-1,3-dioxin-4-ones 4a-n were obtained in good to excellent yields. The catalyst system provides high efficiency at low load using electronically diverse coupling partners. The obtained 2,2,6-trimethyl-5-aryl-1,3-dioxin-4-ones were transformed into corresponding alpha-aryl-beta-ketoesters 6 by reaction with an alcohol in the absence of solvent. (C) 2009 Elsevier Ltd. All rights reserved.