3,3-dicyclopropylprop-2-en-1-ol | 332104-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-dicyclopropylprop-2-en-1-ol
• CAS: 332104-88-8
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: LWRFGPYANZQTLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  3,3-dicyclopropylprop-2-en-1-ol 在 palladium diacetate lithium aluminium tetrahydride 、 potassium tert-butylate 、 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 、 苯酚 为溶剂， 反应 20.0h， 生成 tetracyclopropylmethane
  参考文献：
  名称：

  四环丙基甲烷：具有S4对称性的独特烃。

  摘要：

  DOI：

  10.1002/1521-3773(20010105)40:1<180::aid-anie180>3.0.co;2-k
• 作为产物：
  描述：

  ethyl 3,3-dicyclopropylacrylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以84%的产率得到3,3-dicyclopropylprop-2-en-1-ol
  参考文献：
  名称：

  6-环烷基乙烯基取代的1,2,4-三恶烷的合成及抗疟活性。

  摘要：

  已经制备了6-环烷基乙烯基取代的1,2,4-三恶烷6-15，并在小鼠中测试了其对多药耐药性约氏疟原虫的抵抗力。活性最高的三恶烷11为经治疗的小鼠提供80％的保护。11的进一步衍生化导致抗疟活性降低。

  DOI：

  10.1016/j.bmc.2004.08.042

文献信息

• Novel Silicon-Based Patchouli Odorants of the Trialkyl(1-hydroxy-1-methylethyl)silane Type: Design, Synthesis, and Olfactory Properties
  作者：Astrid Sunderkötter、Sabine Lorenzen、Reinhold Tacke、Philip Kraft

  DOI：10.1002/chem.201000549

  日期：2010.7.5

  synthesized and studied for their olfactory properties. All of the silanes studied exhibit at least one of the main patchouli odor descriptors ‘woody,’ ‘earthy,’ and ‘camphoraceous,’ and some even exhibit all of them. The silanes MeR2SiC(OH)Me2 (12) and R3SiC(OH)Me2 (14) (R=cyclopropyl) were found to resemble natural patchouli oil most closely, with an even lower odor threshold than the natural lead

  叔丁基（1-羟基-1-甲基乙基）二甲基硅烷（5），一硅杂取代的开环衍生物的最近报道广藿香引线结构（4A - [R *，8α - [R *） - 1,1,8a-trimethyldecahydronaphthalene甲基-4a-醇（4），和一些相关的三烷基（1-羟基-1-甲基乙基）硅烷和进一步的衍生物，化合物8 - 24，用不同的硅结合的取代基（ME等，我PR，ç PR，吨卜，i Bu，c Pent，乙烯基，SiMe 3）合成并研究其嗅觉特性。所研究的所有硅烷均表现出至少一种主要的广香气味描述符“木质”，“土”和“樟脑”，甚至有些甚至全部表现出来。发现硅烷MeR 2 SiC（OH）Me 2（12）和R 3 SiC（OH）Me 2（14）（R =环丙基）最接近天然广patch香油，气味阈值比天然铅更低结构（-）-广atch香酚（1）。为了完成该结构与气味的关系研究，需要使用12和14的碳类似物（Si
• Magnesium-Alkoxide Directed Photoaddition of Tetrahydrofurans to γ,γ-Disubstituted Allylic Alcohols
  作者：Yutaka Ukaji、Yasutaka Watanabe、Takahiro Sakai、Hajime Maeda、Masahito Segi

  DOI：10.3987/com-15-s(t)65

  日期：——

  Magnesium-alkoxide directed photoaddition of tetrahydrofurans to gamma,gamma-disubstituted allylic alcohols was achieved. When the allylic alcohols were treated with Grignard reagent in THF under light, the corresponding gamma-(2-tetrahydrofuryl) substituted alcohols were regioselectively obtained in up to 82% yield. The conversion of the hydroxyl group to the corresponding bromomagnesium alkoxide was crucial.
• Conformational Dynamics of Tetraisopropylmethane and of Tetracyclopropylmethane¹
  作者：J. Edgar Anderson、Armin de Meijere、Sergei I. Kozhushkov、Lodovico Lunazzi、Andrea Mazzanti

  DOI：10.1021/ja017526j

  日期：2002.6.1

  Tetraisopropylmethane (1) exists in solution as a mixture of two types of conformers (D(2d) and S(4) time-averaged symmetry) in the ratio 93:7 at - 110 degreesC, interconverting with a barrier of 9.7 kcal mol(-1). Molecular mechanics calculations and the multiplicity of NMR signals at low temperature allow the assignment of these conformations. The only conformation populated in tetracyclopropylmethane (2) is the same type as the minor conformation (S(4) time-averaged symmetry) populated in 1. 13 C NMR spectra at about -180 degreesC show that degenerate versions of this conformation interconverting with a barrier of 4.5 kcal mol-1. Molecular mechanics calculations that characterize the six possible conformational types for these molecules, and the most important interconversion pathways, are reported. Calculated and experimental barriers match satisfactorily well.