trans-1-(1-propenyl)cyclohexanol | 6244-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-(1-propenyl)cyclohexanol
• 英文别名: 1-(1'-propenyl)-cyclohexan-1-ol；(E)-1-(1-propenyl)cyclohexanol；1-Propenyl-cyclohexanol-(1)；1-Propenyl-cyclohexanol；1-Prop-1-enylcyclohexan-1-ol
• CAS: 6244-44-6
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: GZNNZZDBIAGVDE-UHFFFAOYSA-N

物化性质

• 沸点：
  82 °C(Press: 13 Torr)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-1-(1-propenyl)cyclohexanol 在 CoCl₂ 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-(cyclohexylidene)-2-propanol
  参考文献：
  名称：

  Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles

  摘要：

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.

  DOI：

  10.1021/jo00114a013
• 作为产物：
  描述：

  propylidene cyclohexane oxide 在 lithium diethylamide 作用下， 生成 trans-1-(1-propenyl)cyclohexanol
  参考文献：
  名称：

  Base-induced rearrangement of epoxides to allylic alcohols. III. Alkylidenecycloalkane oxides

  摘要：

  DOI：

  10.1021/jo00809a011

文献信息

• Arene-catalysed reductive desulfonylation and desulfinylation reactions: New routes for alkyllithiums
  作者：Emma Alonso、David Guijarro、Miguel Yus

  DOI：10.1016/0040-4020(94)01116-h

  日期：1995.2

  The reaction of alkyl phenyl sulfones (1) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound or chlorotrimethylsilane (Barbier-type conditions) in THF at temperatures ranging between −78 and 20°C leads, after hydrolysis, to the expected products (2) arising from the corresponding alkyllithium generated in situ. When the same methodology

  烷基苯基砜（1）与过量的锂粉和催化量的萘（8摩尔％）在羰基化合物或三甲基氯硅烷（Barbier型条件）存在下于THF中在-78至78的温度范围内反应水解后，20°C导致生成预期的产物（2），该产物由原位生成的相应烷基锂产生。当将相同的方法应用于环丁砜（3）或不同的烷基苯基亚砜（6）时，分别获得环状亚磺酸盐5或产物2，通常收率不高。
• Exploration of the diastereoselectivity in an unusual Grignard reaction and its application towards the synthesis of styryl lactones 7-epi-(+)-goniodiol and 8-epi-(−)-goniodiol
  作者：Subhash P. Chavan、Harshali S. Khatod、Tamal Das、Kumar Vanka

  DOI：10.1039/c6ra03192g

  日期：——

  chain secondary alcohols possessing a terminal olefin, which are synthetically important intermediates. As an application of this method, the diastereoselective synthesis of styryl lactones viz. 7-epi-(+)-goniodiol (29) and 8-epi-(−)-goniodiol (30) has been achieved.

  探索了不寻常的非对映选择性格氏试剂，其中格氏试剂衍生自1，n-二卤代烷烃。由于在苄基位置上与丙酮酸酯相邻的季中心的存在而引起的空间偏向负责以几乎定量的产率形成分子内还原的产物。这种位阻是多种芳香族和脂肪族酯类所观察到的非对映选择性的原因。不寻常的格氏反应可提供具有末端烯烃的长链仲醇，这是合成上重要的中间体。作为该方法的应用，苯乙烯基内酯的非对映选择性合成。7- Epi -（+）-goniodiol（29）和8-epi -（-）-goniodiol（30）已经实现。
• Marcou,A.; Normant,H., Bulletin de la Societe Chimique de France, 1965, p. 3491 - 3494
  作者：Marcou,A.、Normant,H.

  DOI：——

  日期：——
• Palladium(II)-catalyzed carbonylation of 3-buten-1-ols and 3-butyn-1-ols: an efficient synthesis of .gamma.-butyrolactones
  作者：Yoshinao Tamaru、Makoto Hojo、Zenichi Yoshida

  DOI：10.1021/jo00003a036

  日期：1991.2

  Palladium(II)-catalyzed dicarbonylation of 3-buten-1-ols (1) in the presence of propylene oxide and ethyl orthoacetate in methanol-dichloromethane under carbon monoxide at atmospheric pressure afforded alpha-[(methoxycarbonyl)methyl]-gamma-butyrolactones (2) in good yields. This dicarbonylation reaction occurs via stereospecific cis addition. Under similar conditions, 4-(trimethylsilyl)-3-butyn-1-ols (4a and 4b) undergo dicarbonylation to provide cis-dicarbonylated alpha-methylene-gamma-butyrolactones (5a and 5b, respectively). 4-Alkyl-and 4-aryl-3-butyn-1-ols (4c-g), on the other hand, undergo trans alkoxycarbonylation across the triple bond and selectively furnish E tetrasubstituted alpha-methylene-gamma-butyrolactones (6).
• Photosensitized cis/trans isomerization of 1-(1-propenyl)cycloalkenes
  作者：Wayne D. Inman、Kenneth A. J. Sanchez、Manuel A. Chaidez、Donald R. Paulson

  DOI：10.1021/jo00281a032

  日期：1989.9