(2-甲基-环己-1-烯基)-乙醛 | 105463-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2-甲基-环己-1-烯基)-乙醛
• 英文名称: (2-methyl-cyclohex-1-enyl)-acetaldehyde
• 英文别名: 2-(2-Methylcyclohexen-1-yl)acetaldehyde
• CAS: 105463-30-7
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: DJLPAGFPRMZLME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2-甲基-环己-1-烯基)-乙醛 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 4-(2'-Methyl-1'-cyclohexenyl)-2-buten-1-ol
  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：

  2-甲基环己酮 在 potassium hydrogensulfate 、 乙醚 、 magnesium 、 溶剂黄146 、 苯 作用下， 生成 (2-甲基-环己-1-烯基)-乙醛
  参考文献：
  名称：

  维生素D领域的研究。第一部分。含有速甾醇发色团的三烯的合成

  摘要：

  DOI：

  10.1039/jr9550000320

文献信息

• 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：——
• METHOD OF USING ORGANIC COMPOUNDS
  申请人：Givaudan SA

  公开号：EP2046147B1

  公开（公告）日：2013-05-01
• Method of Using Organic Compounds
  申请人：Grab Willi

  公开号：US20090311403A1

  公开（公告）日：2009-12-17

  A method of using organic compounds and providing slow release flavoring in or for food products wherein flavor precursors are added to flavor compositions and/or food products and release flavor compounds upon consumption of the food products, and novel flavor precursor compounds. The flavor precursors can be prepared from monoglycerides and flavor compounds which comprise one or more carbonyl groups.
• 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.
• Studies in the vitamin D field. Part I. Synthesis of trienes containing the tachysterol chromophore
  作者：E. A. Braude、O. H. Wheeler

  DOI：10.1039/jr9550000320

  日期：——