spiro<4.5>deca-6,9-diene-2,8-dione | 52727-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro<4.5>deca-6,9-diene-2,8-dione
• 英文别名: spiro[4.5]deca-6,9-diene-3,8-dione
• CAS: 52727-26-1
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: JZGXWMROJKTHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  spiro<4.5>deca-6,9-diene-2,8-dione 在 aluminum tri-tert-butoxide 作用下， 生成 2-hydroxyspiro<4.5>deca-6,9-dien-8-one
  参考文献：
  名称：

  Iwata, Chuzo; Yamada, Minoru; Ida, Yasuo, Chemical and pharmaceutical bulletin, 1988, vol. 36, # 8, p. 2864 - 2871

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二氧杂-二螺[4.1.5.2]十四碳-8,11-二烯-10-酮 在 溶剂黄146 作用下， 生成 spiro<4.5>deca-6,9-diene-2,8-dione
  参考文献：
  名称：

  Dorling; Harley-Mason, Chemistry and industry, 1959, p. 1551

  摘要：

  DOI：

文献信息

• Stereoselectivity Control by Oxaspiro Rings during Diels−Alder Cycloadditions to Cross-Conjugated Cyclohexadienones:  The <i>Syn</i> Oxygen Phenomenon
  作者：Katsuo Ohkata、Yukiko Tamura、Brandon B. Shetuni、Ryukichi Takagi、Wataru Miyanaga、Satoshi Kojima、Leo A. Paquette

  DOI：10.1021/ja047027t

  日期：2004.12.1

  parameters were determined for the cycloaddition of 1a and 2a to cyclopentadiene. The rate acceleration profile of solvents was in the order CF(3)CH(2)OH >> CH(3)CN approximately CH(2)Cl(2) for the production of 9a from 1a and CF(3)CH(2)OH >> CH(2)Cl(2) > CH(3)CN for the production of 21a from 2a, respectively. This spread in polarity had no major impact on product distribution, a phenomenon also reflected

  已经研究了在涉及具有不同反应性的二烯的螺环交叉共轭环己二烯酮的 Diels-Alder 加成中操作的非对映面选择性。该研究包括醚系列 1a-c 以及内酯/酮对 2a/2b。在所有情况下，优选的 [4+2] 环加成途径由从 pi 表面顺式键合到氧原子组成。4-取代的-4-甲基-2,5-环己二烯酮（单环系统）也进行了检查，发现它们优先从带有两个基团在4位吸电子更多的表面形成键。确定了 1a 和 2a 环加成生成环戊二烯的动力学参数。溶剂的速率加速曲线的顺序为 CF(3)CH(2)OH >> CH(3)CN 大约 CH(2)Cl(2) 用于从 1a 生产 9a 和 CF(3)CH(2)OH >> CH(2)Cl(2) > CH(3)CN 用于生产21a 分别来自 2a。这种极性分布对产品分布没有重大影响，这一现象也反映在 4-取代-4-甲基-2,5-环己二烯酮在可比条件下的行为中。这些实验事实的理论评估是在
• A modified procedure for the synthesis of spirodienones from phenolic .ALPHA.-diazoketones.
  作者：CHUZO IWATA、KAZUYUKI MIYASHITA、TOMOKO IMAO、KOJI MASUDA、NANA KONDO、SHUJI UCHIDA

  DOI：10.1248/cpb.33.853

  日期：——

  Rhodium (II) pivalate, rhodium (II) acetate, and palladium (II) acetate were found to be effective catalysts for the synthesis of spirodienones from phenolic α-diazoketones.

  新戊酸铑(II)、乙酸铑(II)和乙酸钯(II)被发现是从酚类α-重氮酮合成螺二烯酮的有效催化剂。
• A Unique and Convenient One-Step Preparation of Spiro[4.5]deca-6,9-diene-2,8-dione
  作者：Adam M. Fivush、Sanford R. Strunk

  DOI：10.1080/00397919608003532

  日期：1996.4

  Abstract A facile one-step synthesis of spiro[4.5]deca-6,9-diene-2,8-dione(1) from p-methoxyphenylacetyl chloride via a Friedel-Crafts acylation followed by ring closure is reported.

  摘要 报道了一种从对甲氧基苯乙酰氯通过 Friedel-Crafts 酰化和闭环简单一步合成螺 [4.5] deca-6,9-diene-2,8-dione(1) 的方法。
• Spiro-fused 2,5-cyclohexadienones from thermal 1,3-shifts in quinol vinyl ethers. Reactions in nonbenzenoid systems and limitations of the chemistry
  作者：John S. Swenton、David Bradin、Bradley D. Gates

  DOI：10.1021/jo00021a037

  日期：1991.10

  Addition of functionalized organolithium compounds to quinone monoketals furnished 4-hydroxy-2,5-cyclo-hexadienone derivatives. The 4-hydroxyl group of these molecules was then transformed into a vinyl ether, and the thermal [1,3]-shift chemistry of these functionalized vinyl ethers was studied. In dienone derivatives wherein a [3,3]-sigmatropic shift was not stereoelectronically possible, these molecules underwent thermal and photochemical [1,3]-oxygen-to-carbon migration, affording spiro-2,5-cyclohexadienones in good yield. However, for compounds in which the [3,3]-shift involving the vinyl ether was possible, this reaction occurred at or below room temperature. 1,5-Cyclooctadienebis(methyldiphenylphosphine)iridium hexafluorophosphate was found to be an especially efficient catalyst for the allyl-to-vinyl ether isomerization in these systems.
• Efficient synthesis of vinyl ethers of spiroquinol ketals and their high-yield photochemical oxygen-to-carbon [1,3]-shift to spiro-fused 2,5-cyclohexadienones
  作者：John S. Swenton、Andrew Callinan、Shaopeng Wang

  DOI：10.1021/jo00027a017

  日期：1992.1

  An efficient route to spiroquinol vinyl ethers involves addition of a 1-lithio-2-(trimethylsilyl)acetylene-substituted benzene to the monoethylene ketal of benzoquinone followed by desilylation/cyclization of the resulting product to give vinyl ethers of spiroquinol ketals. A high-yield photochemical conversion of these vinyl ethers of spiroquinol ketals to ketals of spiro-fused 2,5-cyclohexadienones has been developed. A complication in some of these photochemical reactions is formation of secondary products from light absorbed by the product, spiro dienone ketals. This has been solved by conducting the reaction in the presence of piperylene, which quenches the triplet-state chemistry of the product spiro dienone ketal without altering the singlet excited-state chemistry of the quinol ketal vinyl ether. The quantum yield for the photochemical [1,3]-shift reaction in a methyl-substituted vinyl ether is 0.4. Finally, irradiation of quinol spiro vinyl ethers was also observed to give spiro dienones in good yields. Although the spiro dienone is absorbing light in competition with starting quinol vinyl ether in this system, a high yield of product was obtained. The unexpected photochemical stability of these spiro dienones is discussed. The chemistry reported herein establishes an efficient high-yield route to spiro-fused 2,5-cyclohexadienones and their ketals under very mild conditions.