1-(hex-5-enyl)cyclohexanol | 213971-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(hex-5-enyl)cyclohexanol
• 英文别名: 1-Hex-5-enylcyclohexan-1-ol
• CAS: 213971-97-2
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: MQWMZYBADLYEGK-UHFFFAOYSA-N

物化性质

• 沸点：
  86 °C(Press: 0.125 Torr)
• 密度：
  0.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  1-(hex-5-enyl)cyclohexanol 在 sodium hydride 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1-(6-(benzyloxy)hexyl)cyclohexan-1-ol
  参考文献：
  名称：

  三光气和DMAP作为叔醇化学选择性脱水的温和试剂

  摘要：

  据报道，三光气和DMAP作为温和试剂用于叔醇的化学选择性脱水。该反应在室温下在二氯甲烷中进行，很容易被宽范围的底物所耐受，优先以（E）-几何结构产生烯烃。尽管通常优选霍夫曼产物的形成，但是当反应在二氯乙烷中在回流下进行时，观察到烯烃对Zaitzev产物的选择性的急剧变化。

  DOI：

  10.1021/acs.orglett.9b01959
• 作为产物：
  描述：

  1,6-二溴己烷 在 乙醚 、 magnesium 作用下， 生成 1-(hex-5-enyl)cyclohexanol
  参考文献：
  名称：

  The Synthesis and Oxidation of Polymethylene Bis-cycloalkenes¹

  摘要：

  DOI：

  10.1021/ja01113a038

文献信息

• Convenient preparation of metals deposited on solid supports and their use in organic synthesis
  作者：Mieczyslaw Ma̧kosza、Piotr Nieczypor、Karol Grela

  DOI：10.1016/s0040-4020(98)00625-5

  日期：1998.9

  “High-surface alkali metals” can be conveniently prepared via deposition of corresponding metals on various supports such as sodium chloride, polyethylene, polypropylene and cross-linked polystyrene from their solutions in liquid ammonia. Alkali metals deposited on polymeric supports can be stored in form of stable suspensions in inert solvents and used for the acyloin and Dieckmann condensations and

  “高表面碱金属”可通过将相应的金属从其在液氨中的溶液沉积在各种载体（例如氯化钠，聚乙烯，聚丙烯和交联的聚苯乙烯）上而方便地制备。沉积在聚合物载体上的碱金属可以在惰性溶剂中以稳定的悬浮液形式存储，并用于酰基环和Dieckmann缩合反应以及有机锂的制备。将负载的碱金属的悬浮液添加到氯化锌溶液中，可以在聚合物载体上得到活性锌，可以将其用于Reformatski和Barbier反应。
• Intramolecular carbolithiation promoted by a DTBB-catalysed chlorine–lithium exchange
  作者：Miguel Yus、Rosa Ortiz、Fernando F Huerta

  DOI：10.1016/j.tet.2003.09.012

  日期：2003.10

  The reaction of 6-chlorohex-1-ene 1 with lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at −78°C gives the corresponding organolithium intermediate 2, which by reaction with different electrophiles affords, after hydrolysis with diluted hydrochloric acid, the expected products 3. The same reaction performed at −30°C gives cyclopentyl derivatives 5, probably

  6-氯己-1-烯1与锂粉和催化量的4,4'-二叔丁基联苯（DTBB，5％摩尔）在THF中于-78°C反应，得到相应的有机锂中间体2，通过与不同的亲电试剂反应，经稀盐酸水解后，可提供预期的产物3。在-30℃下进行的相同反应可能通过将开链中间体2环化而得到环状有机锂化合物4，从而得到环戊基衍生物5。当起始材料中的双键包含烷基取代基时，例如化合物6和9，相应的环化被抑制，因此分别获得了相应的无环产物8和11。然而，当在相同位置上的取代基是苯基时，如在原料12和15中一样，分别分离了环化产物14和17。在第二起始氯化物材料18的情况下，该反应可以针对分别在-78或-30℃下工作的无环产物20或环状产物22，如在未取代的情况下发生的那样。氯化物1。对于叔氯衍生物如图23所示，由于相应的叔有机锂中间体24的极大的不稳定性，因此即使在-78℃也仅发生了质子提取，因此在-30℃下仅可以分离环状化合物27。
• DTBB-catalysed lithiation of 6-chloro-1-hexene and related systems: synthetically useful temperature-dependent behaviour
  作者：Miguel Yus、Rosa Ortiz、Fernando F Huerta

  DOI：10.1016/s0040-4039(02)00415-x

  日期：2002.4

  The reaction of 6-chloro-1-hexene 1 with lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at −78°C gives the corresponding organolithium intermediate 2, which by reaction with different electrophiles [ButCHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe] affords, after hydrolysis with water, the expected products 3. The same reaction performed at −30°C gives cyclopentyl

  6-氯-1-己烯的反应1与锂粉末和4,4'-二-催化量叔在THF -butylbiphenyl（DTBB，5％摩尔）在-78℃下，得到相应的有机锂中间体2，通过与不同的亲电子[卜反应吨CHO，苯甲醛，等2 CO，（CH 2）5 CO，PhCOMe]得到，用水水解后，预期的产品3。在-30℃下进行的相同反应可能通过将开链中间体2环化而得到环状有机锂化合物4，从而得到环戊基衍生物5。对于三阶导数6，由于相应的叔有机锂中间体7的极大的不稳定性，在-30℃下仅环状化合物10可以被分离，该叔有机锂中间体7甚至在-78℃下也经历了质子提取。在-78℃或-30℃下从烯丙基2-氯-苯基醚11中仅分离出相应的环状化合物14。在所有情况下，都假定发生了比自由基更好的碳负离子环化。
• Nitro-Substituted Hoveyda−Grubbs Ruthenium Carbenes:  Enhancement of Catalyst Activity through Electronic Activation
  作者：Anna Michrowska、Robert Bujok、Syuzanna Harutyunyan、Volodymyr Sashuk、Grigory Dolgonos、Karol Grela

  DOI：10.1021/ja048794v

  日期：2004.8.1

  The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta- and para-substituted complexes are attractive from a practical point of view. These catalysts operate in very mild conditions and can be successfully applied in various types of metathesis [ring-closing metathesis, cross-metathesis (CM), and enyne metathesis]. Although the presence of a NO2 group leads to catalysts that are dramatically more active than both the second-generation Grubbs's catalyst and the phosphine-free Hoveyda's carbene, enhancement of reactivity is somewhat lower than that observed for a sterically activated Hoveyda-Grubbs catalyst. Attempts to combine two modes of activation, steric and electronic, result in severely decreasing a catalyst's stability. The present findings illustrate that different Ru catalysts turned out to be optimal for different applications. Whereas phosphine-free carbenes are catalysts of choice for CM of various electron-deficient substrates, they exhibit lower reactivity in the formation of tetrasubstituted double bonds. This demonstrates that no single catalyst outperforms all others in all possible applications.
• Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
  作者：Moshood O. Ganiu、Alexander H. Cleveland、Jarrod L. Paul、Rendy Kartika

  DOI：10.1021/acs.orglett.9b01959

  日期：2019.7.19

  The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the

  据报道，三光气和DMAP作为温和试剂用于叔醇的化学选择性脱水。该反应在室温下在二氯甲烷中进行，很容易被宽范围的底物所耐受，优先以（E）-几何结构产生烯烃。尽管通常优选霍夫曼产物的形成，但是当反应在二氯乙烷中在回流下进行时，观察到烯烃对Zaitzev产物的选择性的急剧变化。