1-[4-(t-butyldimethylsilanyloxy)phenyl]penta-3,4-dien-2-one | 219660-41-0

• 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: 1-[4-(t-butyldimethylsilanyloxy)phenyl]penta-3,4-dien-2-one
• 英文别名: p-tert-butyldimethylsiloxybenzyl allenyl ketone
• CAS: 219660-41-0
• 化学式: C₁₇H₂₄O₂Si
• 分子量: 288.462
• InChiKey: PUKTXVJOZPECFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(t-butyldimethylsilanyloxy)phenyl]penta-3,4-dien-2-one 在 mercury(II) perchlorate 水 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以84%的产率得到4-methyl-spiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Mercury(II)-Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)-, Palladium(II)- and Brønsted Acid-Catalyzed Reactions

  摘要：

  The allenyl p-methoxybenzyl ketone 3a and allenyl p-siloxybenzyl ketones 6b selectively delivered three different products with three different transition metal-catalysts. With Hg(II)-catalysts a spiro[4.5]decene 9, with Ag(I)-catalysts a 2-substituted furan (10/11) and with Pd(II)-catalysts a 2,4-disubstituted furan (8/12) was formed. Only with perchloric acid the intermolecular addition of water to the allene, leading to 1,3-dicarbonyl compounds 7, was observed. While with the corresponding allenyl o-methoxybenzyl ketone 3b the Ag(I)- and Pd(II)-catalysts provided the expected products, the mercury-catalyst led to a new and interesting side-product rac-17 which combined both the furan moiety and the spiro[4.5]decene moiety. Efforts to prepare allenyl hydroxybenzyl ketones failed, in one case a small amount of a 5H-benzo[b]oxepin-4-one 21 was isolated. It also was not possible to extend the spirocyclization to allenyl p-siloxyphenyl ketone 6a or allenyl 2-(p-siloxyphenyl)ethyl ketone 6c.

  DOI：

  10.1002/(sici)1521-3897(200001)342:1<40::aid-prac40>3.0.co;2-v
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.25h， 生成 1-[4-(t-butyldimethylsilanyloxy)phenyl]penta-3,4-dien-2-one
  参考文献：
  名称：

  Mercury(II)-Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)-, Palladium(II)- and Brønsted Acid-Catalyzed Reactions

  摘要：

  The allenyl p-methoxybenzyl ketone 3a and allenyl p-siloxybenzyl ketones 6b selectively delivered three different products with three different transition metal-catalysts. With Hg(II)-catalysts a spiro[4.5]decene 9, with Ag(I)-catalysts a 2-substituted furan (10/11) and with Pd(II)-catalysts a 2,4-disubstituted furan (8/12) was formed. Only with perchloric acid the intermolecular addition of water to the allene, leading to 1,3-dicarbonyl compounds 7, was observed. While with the corresponding allenyl o-methoxybenzyl ketone 3b the Ag(I)- and Pd(II)-catalysts provided the expected products, the mercury-catalyst led to a new and interesting side-product rac-17 which combined both the furan moiety and the spiro[4.5]decene moiety. Efforts to prepare allenyl hydroxybenzyl ketones failed, in one case a small amount of a 5H-benzo[b]oxepin-4-one 21 was isolated. It also was not possible to extend the spirocyclization to allenyl p-siloxyphenyl ketone 6a or allenyl 2-(p-siloxyphenyl)ethyl ketone 6c.

  DOI：

  10.1002/(sici)1521-3897(200001)342:1<40::aid-prac40>3.0.co;2-v

文献信息

• 10.1002/1521-3773(20000703)39
  作者：Stephen、Hashmi、Schwarz, Lothar、Choi, Ji-Hyun、Frost, Tanja M.

  DOI：10.1002/1521-3773(20000703)39

  日期：——
• Mercury(II)-catalyzed synthesis of spiro[4.5]decatrienediones in the presence of water
  作者：A.Stephen K. Hashmi、Lothar Schwarz、Michael Bolte

  DOI：10.1016/s0040-4039(98)02057-7

  日期：1998.12

  Treatment of the easily available p-methoxybenzyl allenyl ketone 2 or the (p-tert-butyldimethylsiloxybenzyl) allenyl ketone 9 with 1% Hg(ClO4)(2) in acetonitrile/water provided good yields of the spiro[4.5]deca-3,5,9-triene-2,8-dione 6c. The Hg(II)-catalyzed addition of water to the allene was much slower, the 1,3-diketone 7 was only a minor side-product. The isomeric a-methoxybenzyl allenyl ketone 12 formed some spiro[4.5]deca-3,7,9-triene-2,6-dione 13, the side-reactions were the addition of water and a new spirocyclization/dimerization leading to 15. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Mercury(II)-Catalyzed Synthesis of Spiro[4.5]decatrienediones from Allenyl Ketones and Comparison with Silver(I)-, Palladium(II)- and Brønsted Acid-Catalyzed Reactions
  作者：A. Stephen K. Hashmi、Lothar Schwarz、J. W. Bats

  DOI：10.1002/(sici)1521-3897(200001)342:1<40::aid-prac40>3.0.co;2-v

  日期：2000.1

  The allenyl p-methoxybenzyl ketone 3a and allenyl p-siloxybenzyl ketones 6b selectively delivered three different products with three different transition metal-catalysts. With Hg(II)-catalysts a spiro[4.5]decene 9, with Ag(I)-catalysts a 2-substituted furan (10/11) and with Pd(II)-catalysts a 2,4-disubstituted furan (8/12) was formed. Only with perchloric acid the intermolecular addition of water to the allene, leading to 1,3-dicarbonyl compounds 7, was observed. While with the corresponding allenyl o-methoxybenzyl ketone 3b the Ag(I)- and Pd(II)-catalysts provided the expected products, the mercury-catalyst led to a new and interesting side-product rac-17 which combined both the furan moiety and the spiro[4.5]decene moiety. Efforts to prepare allenyl hydroxybenzyl ketones failed, in one case a small amount of a 5H-benzo[b]oxepin-4-one 21 was isolated. It also was not possible to extend the spirocyclization to allenyl p-siloxyphenyl ketone 6a or allenyl 2-(p-siloxyphenyl)ethyl ketone 6c.