3-(3-methyl-3-butenyl)cyclohex-2-enone | 84599-57-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-methyl-3-butenyl)cyclohex-2-enone
• 英文别名: 3-(3-Methylbut-3-enyl)cyclohex-2-en-1-one
• CAS: 84599-57-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: ZDNFTWKQGCRUFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(3-methyl-3-butenyl)cyclohex-2-enone 以2%的产率得到
  参考文献：
  名称：

  WOLFF, S.;AGOSTA, W. C., J. AMER. CHEM. SOC., 1983, 105, N 5, 1292-1299

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Methyl-tricyclo[4.4.0.0^1,4]decan-7-one 生成 3-(3-methyl-3-butenyl)cyclohex-2-enone
  参考文献：
  名称：

  WOLFF, S.;AGOSTA, W. C., J. AMER. CHEM. SOC., 1983, 105, N 5, 1292-1299

  摘要：

  DOI：

文献信息

• Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions
  作者：Prashant A. Waske、Jochen Mattay

  DOI：10.1016/j.tet.2005.08.034

  日期：2005.10

  Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5-exo-trig mode of

  已经合成了具有苄基，烯烃或炔属侧链的各种环稠合的环丙基甲硅烷基醚。氧化光诱导电子转移（PET）后，环丙烷环打开并形成反应性β-酮基，该基团经过分子内环化。在某些情况下，我们仅观察到开环的非环化产物的形成。用烯烃侧链发生5- exo - trig环化模式，而不是6- endo - trig环化模式，而在炔属侧链的情况下，我们观察到6- endo环化。
• Intramolecular photocycloaddition reactions of 1-acyl-3-oxa-1,5-hexadienes
  作者：Albert R. Matlin、David J. McGarvey

  DOI：10.1016/s0040-4039(00)95597-7

  日期：——

  The regioselectivity of the intramolecular [2+2] photocycloadditions of 1-Acyl-3-oxa-1,5-hexadienes appears, in general, to follow “rule of five” closure and give annelated 2-oxa-bicyclo[2.1.1]hexanes.

  1-Acyl-3-oxa-1,5-己二烯的分子内[2 + 2]光环加成反应的区域选择性总体上遵循“五个规则”的封闭关系，并产生退火的2-oxa-双环[2.1.1]正己烷。
• Construction of fused- and spiro-oxa-[n.2.1] skeletons by a tandem epoxide rearrangement/intramolecular [3+2] cycloaddition of cyclopropanes with carbonyls
  作者：Lu-Feng Wang、Zi-Fa Shi、Xiao-Ping Cao、Bao-Sheng Li、Peng An

  DOI：10.1039/c4cc02641a

  日期：——

  A Lewis acid promoted tandem reaction of epoxide rearrangement and intramolecular [3+2] cycloaddition reaction of cyclopropanes with carbonyls formed by epoxide rearrangement in situ, which were obtained with difficulty by a general method, is reported. A wide variety of fused- and spiro-oxa-[n.2.1] skeletons could be efficiently constructed.

  报道了路易斯酸促进的环氧化物重排的串联反应和环丙烷与通过原位环氧化物重排形成的羰基的分子内[3 + 2]环加成反应，这是通过常规方法难以获得的。可以有效地构建各种各样的熔融和螺氧基-[n.2.1]骨架。
• AlCl₃‐Promoted Conia‐Ene‐Related Cyclization of α,ω‐Diethylenic Ketones and 1,2‐ or 1,3‐Hydroalkenylation of Unactivated Cyclopropanes
  作者：Julien Coulomb

  DOI：10.1002/adsc.202300317

  日期：2023.9.5

  α,β-Unsaturated enones possessing an unactivated olefin at the ϵ-, ζ- or η-position underwent an aluminum chloride-promoted Conia-ene-related cyclization, affording unsaturated decalones or hexahydroindenones in generally good yields. Cyclopropanes could be used as olefin surrogates in this process, leading to the same bicyclic products in slightly improved efficiency as the result of 1,2- or 1,3-hydroalkenylation

  在ε-、δ-或η-位具有未活化烯烃的α,β-不饱和烯酮经历氯化铝促进的Conia-ene相关环化，以通常良好的产率提供不饱和十酮或六氢茚酮。在此过程中，环丙烷可用作烯烃替代物，通过 1,2- 或 1,3- 加氢烯基化反应，产生相同的双环产物，但效率略有提高。该方法提供了获得全系列双环或三环烯酮合成子的途径，其中一些可能用作气味剂或用于生物活性分子的合成。
• Regiochemical control in intramolecular photochemical reactions of 1,5-hexadien-3-ones and 1-acyl-1,5-hexadienes
  作者：Steven Wolff、William C. Agosta

  DOI：10.1021/ja00343a036

  日期：1983.3