3-[(2-甲基-2-丙烯-1-基)氧基]-2-环己烯-1-酮 | 112148-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-[(2-甲基-2-丙烯-1-基)氧基]-2-环己烯-1-酮
• 英文名称: 3-(2-Methyl-2-propenoxy)cyclohex-2-en-1-one
• 英文别名: 3-(2-Methyl-2-propenyloxy)-2-cyclohexen-1-one；3-(2-methylprop-2-enoxy)cyclohex-2-en-1-one
• CAS: 112148-00-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: KOGTYQSFOUSXKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-甲基-2-丙烯-1-基)氧基]-2-环己烯-1-酮 以 正己烷 为溶剂， 反应 61.0h， 生成 7-Methyl-9-oxa-tricyclo[5.2.1.0^1,6]decan-5-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-环己二酮 、 2-甲基-2-丙烯-1-醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 3-[(2-甲基-2-丙烯-1-基)氧基]-2-环己烯-1-酮
  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

• 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.