(E)-5,5-dimethyl-2-[4-(phenylsulfonyl)but-2-en-2-yl]-1,3-dioxane | 1606991-68-7

• 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: (E)-5,5-dimethyl-2-[4-(phenylsulfonyl)but-2-en-2-yl]-1,3-dioxane
• 英文别名: 2-[(E)-4-(benzenesulfonyl)but-2-en-2-yl]-5,5-dimethyl-1,3-dioxane
• CAS: 1606991-68-7
• 化学式: C₁₆H₂₂O₄S
• 分子量: 310.414
• InChiKey: QWBFJBAHCZZWFK-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5,5-dimethyl-2-[4-(phenylsulfonyl)but-2-en-2-yl]-1,3-dioxane 、 bis(4-chloro-3-methylbut-2-enyl) sulfone 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以93%的产率得到2,2′-(2E,2′E,6E,6′E)-8,8′-sulfonylbis[6-methyl-4-(phenylsulfonyl)octa-2,6-diene-8,2-diyl]bis(5,5-dimethyl-1,3-dioxane)
  参考文献：
  名称：

  Sulfone-Mediated Syntheses of Crocetin Derivatives: Regioselectivity of Highly Functionalized Building Blocks

  摘要：

  New C-5 sulfone building blocks containing a masked polar end group have been devised for the efficient synthesis of carotenoids with polar termini. Chemoselectivity or the regiochemical issue of the highly functionalized units has been carefully addressed depending on the soft or hard nature of electrophiles. These building blocks have been successfully applied to the syntheses of crocetin derivatives, crocetin dial and the novel crocetin dinitrile.

  DOI：

  10.1021/jo500478u
• 作为产物：
  描述：

  4-氯-2-甲基-巴豆醛 在 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 21.0h， 生成 (E)-5,5-dimethyl-2-[4-(phenylsulfonyl)but-2-en-2-yl]-1,3-dioxane
  参考文献：
  名称：

  Sulfone-Mediated Syntheses of Crocetin Derivatives: Regioselectivity of Highly Functionalized Building Blocks

  摘要：

  New C-5 sulfone building blocks containing a masked polar end group have been devised for the efficient synthesis of carotenoids with polar termini. Chemoselectivity or the regiochemical issue of the highly functionalized units has been carefully addressed depending on the soft or hard nature of electrophiles. These building blocks have been successfully applied to the syntheses of crocetin derivatives, crocetin dial and the novel crocetin dinitrile.

  DOI：

  10.1021/jo500478u

文献信息

• METHOD FOR SYNTHESIZING 2,7-DIMETHYL-2,4,6-OCTATRIENE-1,8-DIALDEHYDE
  申请人：NANJING UNIVERSITY OF TECHNOLOGY

  公开号：US20140378711A1

  公开（公告）日：2014-12-25

  Provided in the present invention is a method for synthesizing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. The synthesis method comprises the following steps: (1) adding acetaldehyde diethyl acetal and ethyl-(1-propenyl)-ether under the effect of a catalyst to produce 1,1,3-triethoxy-2-methyl-butane; (2) pyrolysis synthesizing 1,1,3-triethoxy-2-methyl-butane under the catalytic effects of isoquinoline and p-Toluenesulfonic acid to produce 1-methoxy-2-methyl-1,3-butadiene; (3) dissolving 1-methoxy-2-methyl-1,3-butadiene in anhydrous ethanol solvent for synthesis with a phase transfer catalyst, cetyl-trimethyl ammonium bromide, and a chlorinating agent, trichloroisocyanuric acid, to generate 4,4-diethoxy-3-methyl-1-chloro-butene; (4) combining 4,4-diethoxy-3-methyl-1-chloro-butene with a triphenylphosphine salt to produce a phosphonium salt; and (5) condensing the phosphonium salt under the effects of hydrogen peroxide in conjunction with sodium carbonate solution to generate 1,1,8,8-tetramethyl-2,7-dimethyl-2,4,6-octatriene; then hydrolyzing under acidic conditions to synthesize 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde. The present invention has a simple process route, is easy to operate, and has mild conditions, great yield, and great industrial value.

  本发明提供了一种合成2,7-二甲基-2,4,6-辛三烯-1,8-二醛的方法。合成方法包括以下步骤：(1) 在催化剂的作用下，将乙醛二乙醚和乙基-(1-丙烯基)-醚加入以产生1,1,3-三乙氧基-2-甲基-丁烷；(2) 在异喹啉和对甲苯磺酸的催化作用下，热解合成1,1,3-三乙氧基-2-甲基-丁烷以产生1-甲氧基-2-甲基-1,3-丁二烯；(3) 将1-甲氧基-2-甲基-1,3-丁二烯溶解在无水乙醇溶剂中，与相转移催化剂十六烷基三甲基溴化铵和氯化剂三氯异氰酸酯合成，生成4,4-二乙氧基-3-甲基-1-氯-丁烯；(4) 将4,4-二乙氧基-3-甲基-1-氯-丁烯与三苯基膦盐结合产生膦盐；(5) 在过氧化氢的作用下，与碳酸钠溶液一起对膦盐进行缩合，生成1,1,8,8-四甲基-2,7-二甲基-2,4,6-辛三烯；然后在酸性条件下水解，合成2,7-二甲基-2,4,6-辛三烯-1,8-二醛。本发明具有简单的工艺路线，易于操作，条件温和，产率高，具有很大的工业价值。
• US9187394B2
  申请人：——

  公开号：US9187394B2

  公开（公告）日：2015-11-17
• Sulfone-Mediated Syntheses of Crocetin Derivatives: Regioselectivity of Highly Functionalized Building Blocks
  作者：Eun-Taek Oh、Young-Hun Kim、Jingquan Jin、Liang Su、Jung-Ah Seo、Sangho Koo

  DOI：10.1021/jo500478u

  日期：2014.5.16

  New C-5 sulfone building blocks containing a masked polar end group have been devised for the efficient synthesis of carotenoids with polar termini. Chemoselectivity or the regiochemical issue of the highly functionalized units has been carefully addressed depending on the soft or hard nature of electrophiles. These building blocks have been successfully applied to the syntheses of crocetin derivatives, crocetin dial and the novel crocetin dinitrile.