5-methylenespiro<3.5>nonan-1-one | 81388-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methylenespiro<3.5>nonan-1-one
• 英文别名: 5-Methylidenespiro[3.5]nonan-1-one；9-methylidenespiro[3.5]nonan-3-one
• CAS: 81388-67-2
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: XINCNLFBGXKSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  5-methylenespiro<3.5>nonan-1-one 在 甲基锂 、 对甲苯磺酰肼 作用下， 生成 5-Methylenespiro<3.5>non-1-ene
  参考文献：
  名称：

  Thermal isomerization of a vinylcyclobutene to a cyclohexadiene

  摘要：

  Above 100-degrees-C 5-methylenespiro[3.5]non-1-ene, 1, undergoes cyclobutene ring opening to (E)-triene 2 and apparent 1,3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio. (E)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. Speculation on the 2 to 3 conversion focuses on the possible intermediacy of a 3-vinylcyclohexenocyclobutene, 5. The apparent noninvolvement of a concerted 1,3-shift in the 1 to 3 reaction is discussed.

  DOI：

  10.1021/jo00033a014
• 作为产物：
  描述：

  1,4-二氧杂螺[4.5]癸-6-基-甲醇 在 sodium tetrahydroborate 、 正丁基锂 、 三氟化硼乙醚 、 对甲苯磺酸 、 二乙胺 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 13.5h， 生成 5-methylenespiro<3.5>nonan-1-one
  参考文献：
  名称：

  Preparation and rearrangement of 1,2-dialkenylcyclobutanols. A useful method for synthesis of substituted cyclooctenones

  摘要：

  DOI：

  10.1021/jo00133a007

文献信息

• Regiospecific alkylative ring expansion of 2,2-disubstituted cyclobutanones via .alpha.-lithio selenoxides
  作者：Robert C. Gadwood

  DOI：10.1021/jo00160a034

  日期：1983.6
• GADWOOD, R. C.;LETT, R. M., J. ORG. CHEM., 1982, 47, N 12, 2268-2275
  作者：GADWOOD, R. C.、LETT, R. M.

  DOI：——

  日期：——
• GADWOOD, R. C., J. ORG. CHEM., 1983, 48, N 12, 2098-1201
  作者：GADWOOD, R. C.

  DOI：——

  日期：——
• Thermal isomerization of a vinylcyclobutene to a cyclohexadiene
  作者：Gitendra C. Paul、Joseph J. Gajewski

  DOI：10.1021/jo00033a014

  日期：1992.3

  Above 100-degrees-C 5-methylenespiro[3.5]non-1-ene, 1, undergoes cyclobutene ring opening to (E)-triene 2 and apparent 1,3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio. (E)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. Speculation on the 2 to 3 conversion focuses on the possible intermediacy of a 3-vinylcyclohexenocyclobutene, 5. The apparent noninvolvement of a concerted 1,3-shift in the 1 to 3 reaction is discussed.
• Preparation and rearrangement of 1,2-dialkenylcyclobutanols. A useful method for synthesis of substituted cyclooctenones
  作者：Robert C. Gadwood、Renee M. Lett

  DOI：10.1021/jo00133a007

  日期：1982.6