7-Methyl-8-vinyl-1,4-dioxa-spiro[4.5]dec-7-ene | 89654-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Methyl-8-vinyl-1,4-dioxa-spiro[4.5]dec-7-ene
• 英文别名: 1,4-Dioxaspiro[4.5]dec-7-ene, 8-ethenyl-7-methyl-；8-ethenyl-7-methyl-1,4-dioxaspiro[4.5]dec-7-ene
• CAS: 89654-02-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: LVYIQMQOQRGVIH-UHFFFAOYSA-N

物化性质

• 沸点：
  264.8±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Methyl-8-vinyl-1,4-dioxa-spiro[4.5]dec-7-ene 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 2-(7-Methyl-1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-ethanol
  参考文献：
  名称：

  Oxyanion Orientation in Anionic Oxy-Cope Rearrangements

  摘要：

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.

  DOI：

  10.1021/jo00085a037
• 作为产物：
  描述：

  (7-甲基-1,4-二氧杂螺[4.5]癸-7-烯-8-基)甲醇 在 正丁基锂 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.83h， 生成 7-Methyl-8-vinyl-1,4-dioxa-spiro[4.5]dec-7-ene
  参考文献：
  名称：

  Oxyanion Orientation in Anionic Oxy-Cope Rearrangements

  摘要：

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.

  DOI：

  10.1021/jo00085a037

文献信息

• CHEMOSELECTIVE REDUCTIVE CLEAVAGE OF KETALS AND ACETALS
  作者：R. J. Borders、T. A. Bryson

  DOI：10.1246/cl.1984.9

  日期：1984.1.5

  Utilization of complexed monochloroborane as a reducing agent for ketals and acetals is reported.

  报道了使用络合的一氯硼烷作为缩酮和缩醛的还原剂。
• Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+, J. Org. Chem, 59 (1994) N 6, S 1444-1456
  作者：Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+

  DOI：——

  日期：——
• BORDERS, R. J.;BRYSON, T. A., CHEM. LETT., 1984, N 1, 9-12
  作者：BORDERS, R. J.、BRYSON, T. A.

  DOI：——

  日期：——
• Oxyanion Orientation in Anionic Oxy-Cope Rearrangements
  作者：Eun Lee、Yong Rok Lee、Bongjin Moon、Ohyun Kwon、Mi Seong Shim、Jae Sook Yun

  DOI：10.1021/jo00085a037

  日期：1994.3

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.