cis-4-tert-butylcyclohexanol methyl ether | 15875-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-4-tert-butylcyclohexanol methyl ether
• 英文别名: cis-1-(tert-butyl)-4-methoxycyclohexane；cis-1-tert-butyl-4-methoxycyclohexane；cis-4-t-Butylcyclohexyl methyl ether；cis-4-methoxy-tert-butylcyclohexane；cis-4-t-butyl-1-methoxycyclohexane；4-methoxy-tert-butylcyclohexane
• CAS: 15875-99-7
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: XMLDPBGRPWQRBE-AOOOYVTPSA-N

物化性质

• 沸点：
  190.3±8.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  cis-4-tert-butylcyclohexanol methyl ether 在 HOF* CH₃CN 、 sodium fluoride 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 以90%的产率得到4-叔丁基环己酮
  参考文献：
  名称：

  Oxidative Cleavage of Methyl Ethers Using the HOF.cntdot.CH3CN Complex

  摘要：

  HOF . CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers. Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation. The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bend alpha to the ether moiety. It was found that the more sterically hindered is the C-H bond in question, the slower the reaction. In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place. When labeled (HOF)-O-18 . CH3CN is used on a O-16 methyl ether, the resulting ketone possesses only the heavier oxygen isotope. Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.

  DOI：

  10.1021/jo00130a029
• 作为产物：
  描述：

  3-(TERT-BUTYL)-1-(MESITYLMETHYL)-1H-PYRAZOLE-5-CARBOXYLIC ACID 在 sodium hydride 作用下， 以 乙醚 为溶剂， 生成 cis-4-tert-butylcyclohexanol methyl ether
  参考文献：
  名称：

  甲氧基环己烷衍生物的13 C核磁共振谱。由甲氧基和环碳的13 C化学位移和3 J C，H耦合常数表明，C–OMe键的旋转子种群

  摘要：

  甲氧基13下在methoxycyclohexane衍生物的化学位移可以在关于C-OME键的旋转异构体群的术语和δ合理化1个效果-由与在相邻的取代基的2-和6-位的甲氧基的基团的空间相互作用。还可从C-2和C-6的13 C化学位移，以及C-1的质子和甲氧基-碳原子之间的三键耦合获得有关旋转异构体种群的信息。

  DOI：

  10.1039/p19810001671

文献信息

• Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones
  作者：Mária Bakos、Ádám Gyömöre、Attila Domján、Tibor Soós

  DOI：10.1002/anie.201700231

  日期：2017.5.2

  Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H2, R‐OH or H2O generates the required Brønsted acid in a reversible, “turn on” manner. The method is not only a complementary metal‐free reductive etherification, but also a niche

  在本文中，我们报道了单个沮丧的路易斯对（FLP）催化剂可以促进醛和酮的还原醚化。该反应不需要外源酸催化剂，但是FLP对H 2，R-OH或H 2 O的联合作用以可逆的“开启”方式产生所需的布朗斯台德酸。该方法不仅是一种补充性的无金属还原醚化方法，而且还是醚类的利基方法，这种方法在合成上不方便，甚至很难通过其他合成方案进行操作。
• Trimethysilyl triflate in organic synthesis11Part 11 of this series. Part 10: S. Murata and R. Noyori, Tetrahedron Letters 2107 (1981).
  作者：R. Noyori、S. Murata、M. Suzuki

  DOI：10.1016/s0040-4020(01)93263-6

  日期：——

  Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media. The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.

  三氟甲磺酸三甲基甲硅烷基酯是有机化合物的强大甲硅烷基化剂，并充当催化剂，可加速非质子介质中的各种亲核反应。反应通过甲硅烷基与杂官能团的单中心亲电配位进行，并表现出独特的选择性。
• Light-Promoted Transfer of an Iridium Hydride in Alkyl Ether Cleavage
  作者：Caleb D. Fast、Nathan D. Schley

  DOI：10.1021/acs.organomet.1c00391

  日期：2021.10.11

  A catalytic, light-promoted hydrosilylative cleavage reaction of alkyl ethers is reported. Initial studies are consistent with a mechanism involving heterolytic silane activation followed by delivery of a photohydride equivalent to a silyloxonium ion generated in situ. The catalyst resting state is a mixture of Cp*Ir(ppy)H (ppy = 2-phenylpyridine-κC,N) and a related hydride-bridged dimer. Trends in

  报道了烷基醚的催化、光促进的氢化硅烷化裂解反应。最初的研究与涉及异解硅烷活化的机制一致，然后传递相当于原位生成的甲硅烷基氧鎓离子的光氢化物。催化剂静止状态是 Cp*Ir(ppy)H (ppy = 2-苯基吡啶-κ C , N) 和相关的氢化物桥接二聚体。底物还原选择性的趋势与 C-O 键断裂的非自由基机制一致。在化学计量测试中发现用蓝光照射 Cp*Ir(ppy)H 会增加氢化物向氧鎓离子的传递速率。在羰基氢化硅烷化催化中发现了类似的速率增强，其通过相关机制起作用，也涉及 Cp*Ir(ppy)H 作为静止状态。
• Photoinduced carbamoylation of ethereal C–H bonds using pentafluorophenyl isocyanate
  作者：Shin Kamijo、Tamaki Hoshikawa、Masayuki Inoue

  DOI：10.1016/j.tetlet.2011.03.128

  日期：2011.6

  achieved via photoinduced functionalization of ethereal C–H bonds in the presence of benzophenone at ambient temperature. The carbamoyl group, a one-carbon unit with a high oxidation state, derived from pentafluorophenyl isocyanate (C6F5NCO) is chemoselectively introduced at the position geminal to the oxygen functionality in a single step. The present reaction system effectively activates the tertiary

  在环境温度下，在二苯甲酮存在下，通过光诱导的醚键CH键的官能化，实现了醚的分子间氨基甲酰基化。将源自五氟苯基异氰酸酯（C 6 F 5 NCO）的具有高氧化态的一碳单元氨基甲酰基在单一步骤中化学选择性地引入与氧官能度成对的位置。本反应系统有效地激活了稠合双环系统空间位阻位点的叔碳键，并引入了氨基甲酰基基团，该氨基甲酰基基团随后可用于进一步的合成修饰。
• On the mechanism of base-induced gas-phase elimination reactions of ethers
  作者：Leo J. De Koning、Nico M. M. Nibbering

  DOI：10.1021/ja00240a019

  日期：1987.3

  For the base-induced gas-phase elimination reactions of diethyl ether and cis- and trans-1-tert-butyl-4-methoxy-cyclohexane the kinetic isotope and leaving group effects have been determined as functions of the base strength using the method of Fourier transform ion cyclotron resonance mass spectrometry. The results are interpreted in terms of a variable E2 transition-state structure. Increasing the

  对于二乙醚和顺-和反-1-叔丁基-4-甲氧基-环己烷的碱诱导气相消除反应，动力学同位素和离去基团效应已确定为碱强度的函数，使用的方法是傅里叶变换离子回旋共振质谱。结果根据可变 E2 过渡状态结构进行解释。增加碱强度会导致过渡态向 E2 光谱的碳负离子或 E1cb 区域移动，这也是凝聚相中的普遍现象。此外，似乎消除反应最容易通过过渡态进行，其中 β 氢和离去基团是周面的。如果基板不轻易允许这样的关系，