4,4'-(1,2-phenylene)bis(butan-2-one)

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-(1,2-phenylene)bis(butan-2-one)
• 英文别名: Phenylenedi-2-butanone；4-[2-(3-oxobutyl)phenyl]butan-2-one
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: NZCBCBSSQIMHHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-(1,2-phenylene)bis(butan-2-one) 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以11%的产率得到1-(7-Hydroxy-7-methyl-5,6,8,9-tetrahydrobenzo[7]annulen-6-yl)ethanone
  参考文献：
  名称：

  Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization

  摘要：

  Intramolecular 1,8-diketone aldol reactions Were Studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.

  DOI：

  10.1021/jo9018914
• 作为产物：
  描述：

  3-丁烯-2-醇 、 1,2-二碘苯 在 palladium diacetate N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以56%的产率得到4,4'-(1,2-phenylene)bis(butan-2-one)
  参考文献：
  名称：

  Palladium catalyzed coupling reactions of diiodoarenes with allylic and homoallylic alcohols

  摘要：

  A sequential transformation consisting of a twofold Heck reaction of 1,2-diiodobenzene (14) with allyl alcohol (2) followed by an intramolecular aldol condensation is suitable for the construction of the benzocyclohept-2-ene-2-carboxaldehyde (15). Under the same reaction conditions 1,8-diiodonayhthalene (7) lends to 1-acenaphthenyl-methanol (6), 2-(1-acenaphthenyl)-ethanol (8), 1-(1w-acenaphthenyl)-ethanol (11), 5-(1,8-naphthalena)-nonan-2,8-dione (12) and 5-(1-naphthyl)-3-methylpentan-2-on (13) mainly.

  DOI：

  10.1002/(sici)1521-3897(199902)341:2<138::aid-prac138>3.0.co;2-i

文献信息

• Calix[4]pyrroles with Shortest Possible Strap: Exclusively Selective toward Fluoride Ion
  作者：Ritwik Samanta、B. Sathish Kumar、Pradeepta K. Panda

  DOI：10.1021/acs.orglett.5b01866

  日期：2015.9.4

  Four new calix[4]pyrroles with the shortest possible strap so far through ortho-linking of the aromatic unit have been synthesized, including a naphthalene-derived fluorescent receptor. They show exclusive selectivity toward the fluoride ion as confirmed by H-1 NMR, isothermal titration calorimetry, and fluorescence spectroscopic study. Anion affinity could also be modulated further via functionalization at the strap. Computational analysis displays calix[4]pyrroles binding to fluoride ion in a very unusual 1,3-alternate conformation where the anion resides on the opposite side of the strap.
• Palladium catalyzed coupling reactions of diiodoarenes with allylic and homoallylic alcohols
  作者：Gerald Dyker、Andreas Thöne

  DOI：10.1002/(sici)1521-3897(199902)341:2<138::aid-prac138>3.0.co;2-i

  日期：1999.2

  A sequential transformation consisting of a twofold Heck reaction of 1,2-diiodobenzene (14) with allyl alcohol (2) followed by an intramolecular aldol condensation is suitable for the construction of the benzocyclohept-2-ene-2-carboxaldehyde (15). Under the same reaction conditions 1,8-diiodonayhthalene (7) lends to 1-acenaphthenyl-methanol (6), 2-(1-acenaphthenyl)-ethanol (8), 1-(1w-acenaphthenyl)-ethanol (11), 5-(1,8-naphthalena)-nonan-2,8-dione (12) and 5-(1-naphthyl)-3-methylpentan-2-on (13) mainly.
• Synthesis of the Cores of Hypocrellin and Shiraiachrome: Diastereoselective 1,8-Diketone Aldol Cyclization
  作者：Erin M. O’Brien、Jingxian Li、Patrick J. Carroll、Marisa C. Kozlowski

  DOI：10.1021/jo9018914

  日期：2010.1.1

  Intramolecular 1,8-diketone aldol reactions Were Studied as a tool for the construction of the seven-membered rings of hypocrellin and shiraiachrome. Conditions were identified to obtain the relative stereochemistries present in the two natural products with excellent diastereoselectivity. In addition, a nine-membered ring congener, which has yet to be observed in nature, formed with high selectivity when a hindered amine was used in conjunction with silazide bases.