endo-Bicyclo[3.3.1]nonan-3-ol | 10036-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-Bicyclo[3.3.1]nonan-3-ol
• 英文别名: bicyclo<3.3.1>nonan-3α-ol；3α-Hydroxy-1α(H)-5α(H)-bicyclo<3.3.1>-nonan；endo-Bicyclo<3.3.1>nonan-3-ol；exo-Bicyclo<3.3.1>nonan-3-ol；exo-Bicyclo<3.3.1>nonanol-3
• CAS: 10036-10-9
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: NLJWCMPSDMDINP-AYMMMOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  endo-Bicyclo[3.3.1]nonan-3-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 bicyclo[3.3.1]nonan-3-one
  参考文献：
  名称：

  Bicyclo[3.3.1]nonanes. II. Synthesis and reactions of simple derivatives

  摘要：

  DOI：

  10.1021/jo01280a020
• 作为产物：
  描述：

  双环[3.3.1]壬-3-烯 生成 endo-Bicyclo[3.3.1]nonan-3-ol
  参考文献：
  名称：

  Bicyclo[3.3.1]nonanes. II. Synthesis and reactions of simple derivatives

  摘要：

  DOI：

  10.1021/jo01280a020

文献信息

• Studies on bicyclononanes. Part III. Chair–boat equilibria in bicyclo[3,3,1]nonanes
  作者：R. A. Appleton、Sister C. Egan、J. M. Evans、S. H. Graham、J. R. Dixon

  DOI：10.1039/j39680001110

  日期：——

  The preparation and configurational assignments of the epimeric 3-carboxybicyclo[3,3,1]nonanes are described, and the free energy difference between their methyl esters is measured. The bromination products of bicyclononan-2-one are discussed, and the deamination of a boat cyclohexylamine is reported.

  描述了异构体3-羧基双环[3,3,1]壬烷的制备和构型分配，并测量了它们的甲酯之间的自由能差。讨论了双环壬烷-2-one的溴化产物，并报道了船用环己胺的脱氨基反应。
• 13C-NMR-Spektroskopische und stereochemische untersuchungen—XIV
  作者：Hans-Jörg Schneider、Walther Ansorge

  DOI：10.1016/0040-4020(77)80138-5

  日期：1977.1

  Syntheses and 13C-NMR spectra of bicyclo[3.3.1]nonanes bearing substituents at C-1 (X = F, Cl, Br, J, OR) and C-3 (X = exo Cl, Br, OR; X = endo COOR, CH3, OR) are described. The functional Cα shifts are found to show the known dependence on the electron withdrawing effect of heterosubstituents, including the 1-jodo compound; there is, however, no weakening attenuation effect with tertiary compounds

  合成和13双环的C-NMR谱[3.3.1]壬烷在C-1（X = F，氯，溴，J，OR）和C-3取代基的轴承（X =外型氯，溴，OR; X =描述了内COOR，CH 3或OR）。功能Cα发现这些位移表明已知的依赖于包括1-jodo化合物在内的杂取代基的吸电子作用。但是，正如通常所暗示的那样，三级化合物并没有减弱衰减的作用，而是取代作用比相应的二阶衍生物所观察到的高多达25 ppm。所有化合物的β碳屏蔽可以表示为方形电场效应；环己烷环的1-和3-外-化合物中但导致的在C线性电场效应的变化的展平α，并且甚至更位于C γ。的去屏蔽γ的碳antipenplanar XC α -C β -C γ构不限于结构上的桥头轴承X，它可以的基础上，通过空间键偏振由C合理化α -X偶极子（线性场效应）。在13 C-NMR光谱中，由C-7位置的3-exo-hetero-subsubsubsubsubtess产生的非
• Bicyclo[3.3.1]nonanes as synthetic intermediates. IV. Behavior of bicyclo[3.n.1]alkan-3-ones toward the Baeyer-Villiger oxidation.
  作者：TAKEFUMI MOMOSE、OSAMU MURAOKA、SHOHGO ATARASHI、TAMIKO HORITA

  DOI：10.1248/cpb.27.222

  日期：——

  The Baeyer-Villiger oxidation of bicyclo [3. n. 1] alkan-3-ones and related systems is described. Bicyclo [3. 3. 1] nonan-2-one (8) was oxidized into the corresponding lactone, which was found to be converted into the cis-1, 3-disubstituted cyclohexane system by the subsequent methanolysis. Meanwhile, the 3-oxo system (2) manifested an anomalous inactivity against the oxidation. The"backside steric hindrance"caused by the axial (endo) proton at C-7 was postulated as the origin of the inactivity. The differential reactivity of the ketones in the Baeyer-Villiger reaction of the bicyclic systems (2, 3, 4) enabled the regiospecific lactonization of the bicyclic diketones (17, 18, 19) into the lactones (37, 38, 39), which would be important precursors for specifically substituted medium-sized lactones, to be achieved.

  描述了双环[3.n.1]烷-3-酮和相关系统的拜耳-维利格氧化。双环[3.3.1]壬烷-2-酮（8）被氧化成相应的内酯，发现通过后续的甲醇解转化为顺式-1,3-二取代环己烷系统。同时，3-氧代系统（2）表现出异常的抗氧化性。假设C-7处的轴向（内）质子引起的“背面空间位阻”是不活跃的根源。在双环系统（2、3、4）的拜耳-维利格反应中，酮
• Momose, Takefumi; Muraoka, Osamu; Masuda, Kikuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 9, p. 3730 - 3733
  作者：Momose, Takefumi、Muraoka, Osamu、Masuda, Kikuo

  DOI：——

  日期：——
• Conformational analysis and chromic acid oxidation. The rationalization of the rates of oxidation of secondary alcohols
  作者：Paul Mueller、Jean C. Perlberger

  DOI：10.1021/ja00442a016

  日期：1976.12