3-(2-Propenoxy)cyclopent-2-en-1-one | 112147-94-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 3-(2-Propenoxy)cyclopent-2-en-1-one
• 英文别名: 3-(Allyloxy)-2-cyclopenten-1-one；3-prop-2-enoxycyclopent-2-en-1-one
• CAS: 112147-94-1
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: SWJZZCPWEBQBCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3-(2-Propenoxy)cyclopent-2-en-1-one 以 正己烷 为溶剂， 反应 100.0h， 生成 8-Oxa-tricyclo[4.2.1.0^1,5]nonan-4-one
  参考文献：
  名称：

  Intramolecular photocycloaddition reactions of 3-(2-propenoxy)cyclopent-2-en-1-ones and 3-(2-propenoxy)cyclohex-2-en-1-ones

  摘要：

  The 3-oxa-1,5-hexadienones 4a, 4b, 5a, and 5b undergo intramolecular [2 + 2] photocycloaddition reactions with quantum yields ranging from 0.2 to 0.002. In general, oxa substitution decreases the quantum yields and favors the formation of crossed closure products in comparison to the alkenyl analogs. Irradiation of stereospecifically deuterated dienones 11a and 12a indicate that the intermediate biradical reverts to the starting dienone faster than it proceeds to product. The results are compared with the analogous alkenyl systems. An explanation for changes in regiochemistry, quantum yields, and reversion rates between the two systems is offered.

  DOI：

  10.1021/jo00043a019
• 作为产物：
  描述：

  1,3-环戊二酮 、 烯丙醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 3-(2-Propenoxy)cyclopent-2-en-1-one
  参考文献：
  名称：

  1-酰基-3-oxa-1,5-己二烯的分子内光环加成反应

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)95597-7

文献信息

• Tetraphenylstibonium Methoxide Promoting C-Alkylation of 2-Substituted Cyclic 1,3-Diketones
  作者：Masahiro Fujiwara、Kazuhisa Hitomi、Akio Baba、Haruo Matsuda

  DOI：10.1246/cl.1994.875

  日期：1994.5

  Selective C-alkylation of 2-methyl-1,3-cyclopentanedione and 2-methyl-1,3-cyclohexanedione was performed by using tetraphenylstibonium methoxide (Ph4SbOMe). The presence of a substituent at the 2-position was essential for C-alkylation.

  利用甲氧基四苯基锡鎓（Ph4SbOMe）对 2-甲基-1,3-环戊二酮和 2-甲基-1,3-环己二酮进行了选择性 C-烷基化反应。2 位取代基的存在对 C- 烷基化至关重要。
• 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。
• MATLIN, ALBERT R.;MCGARVEY, DAVID J., TETRAHEDRON LETT., 28,(1987) N 43, 5087-5090
  作者：MATLIN, ALBERT R.、MCGARVEY, DAVID J.

  DOI：——

  日期：——
• Intramolecular photocycloaddition reactions of 3-(2-propenoxy)cyclopent-2-en-1-ones and 3-(2-propenoxy)cyclohex-2-en-1-ones
  作者：Albert R. Matlin、Benjamin E. Turk、David J. McGarvey、Alejandro A. Manevich

  DOI：10.1021/jo00043a019

  日期：1992.8

  The 3-oxa-1,5-hexadienones 4a, 4b, 5a, and 5b undergo intramolecular [2 + 2] photocycloaddition reactions with quantum yields ranging from 0.2 to 0.002. In general, oxa substitution decreases the quantum yields and favors the formation of crossed closure products in comparison to the alkenyl analogs. Irradiation of stereospecifically deuterated dienones 11a and 12a indicate that the intermediate biradical reverts to the starting dienone faster than it proceeds to product. The results are compared with the analogous alkenyl systems. An explanation for changes in regiochemistry, quantum yields, and reversion rates between the two systems is offered.