3-methyl-3-cyclohexen-1-ol | 53783-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-3-cyclohexen-1-ol
• 英文别名: 3-methylcyclohex-3-en-1-ol；3-methylcyclohex-3-enol
• CAS: 53783-91-8
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: HKVFKEJBSWJQMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  3-methyl-3-cyclohexen-1-ol 在 盐酸 、 sodium hydroxide 、 sodium periodate 、 盐酸羟胺 、 sodium acetate 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.0h， 生成 3-(3-methylcyclohex-3-enyloxycarbonyl)-2-oxa-3-azabicyclo<2.2.1>hept-5-ene
  参考文献：
  名称：

  Kirby, Gordon W.; McGuigan, Henry; McLean, David, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1961 - 1966

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-2-环己烯-1-醇 在 正丁基锂 、 (S)-(pyrrolidinemethyl)pyrrolidine 作用下， 以 正己烷 为溶剂， 反应 72.0h， 生成 3-methyl-3-cyclohexen-1-ol
  参考文献：
  名称：

  Solvent-induced stereospecific isomerization of an allylic alcohol to a homoallylic alcohol catalyzed by a chiral lithium amide

  摘要：

  通过使用锂(S)-2-(1-吡咯烷基)吡咯烷酰胺2-Li，将环己烯氧化物1去质子化，从四氢呋喃(THF)改变溶剂为2,5-二甲基四氢呋喃(DMTHF)或二乙醚(DEE)，除了形成2-环己烯-1-醇的锂烷氧基化物3-Li，还形成了同系异构体醇3-环己烯-1-醇的锂烷氧基化物4-Li。结果显示化合物4-Li是由3-Li形成的，但在THF中没有观察到这种重排反应。现在我们证明了由2-Li催化的(S)-3-甲基-2-环己烯-1-醇的锂烷氧基化物(S)-5-Li在溶剂诱导下的异构化反应到(S)-3-甲基-3-环己烯-1-醇的锂烷氧基化物(S)-6-Li是100%立体特异性的。此外，氘标记实验证明质子重排近乎100%是分子内的。关键词：1,3-质子转移、手性锂酰胺、分子内、溶剂诱导异构化、立体特异性。

  DOI：

  10.1139/v98-052

文献信息

• Syntheses with organoboranes. IX. Vinyl- and 1-alkenyldichloroboranes as ethylene and 1-alkene equivalents for the Diels–Alder reaction
  作者：Marek Zaidlewicz、Jacek R Binkul、Wojciech Sokół

  DOI：10.1016/s0022-328x(98)01175-9

  日期：1999.5

  Vinyl- and 1-alkenyldichloroboranes were used as dienophiles for the Diels–Alder reaction with representative aliphatic and cyclic 1,3-dienes. The organoborane adducts were transformed into the corresponding olefins either by protonolysis or by oxidation–mesylation–reduction. Direct protonolysis of the adducts gave in most cases mixtures of olefins whereas the reduction of mesylates with lithium triethylborohydride

  乙烯基和1-烯基二氯硼烷被用作与亲脂性和环状1,3-二烯代表的狄尔斯-阿尔德反应的亲二烯体。有机硼烷加合物通过质子分解或氧化-甲磺酰化-还原转化为相应的烯烃。在大多数情况下，加合物的直接质子分解得到烯烃的混合物，而用三乙基硼氢化锂还原甲磺酸酯则可得到高纯度的纯烯烃。
• Alkylhalovinylboranes: a new class of Diels–Alder dienophiles
  作者：Pablo L. Pisano、Silvina C. Pellegrinet

  DOI：10.1039/c8ra07089j

  日期：——

  The Diels–Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group

  烷基卤乙烯基硼烷的 Diels-Alder 反应已在理论上和实验上进行了研究。烷基卤代乙烯基硼烷比相应的二烷基乙烯基硼烷具有更高的反应性。尽管与环戊二烯反应的内/外选择性很高，但手性类似物的面部选择性却很低。我们的结果表明，硼原子上的烷基被卤素取代会显着增加亲二烯性。
• COOLING SENSATION AGENT COMPOSITION, SENSORY STIMULATION AGENT COMPOSITION AND USE OF THE SAME
  申请人：Komatsuki Yasuhiro

  公开号：US20110081393A1

  公开（公告）日：2011-04-07

  Disclosed is a cooling sensation agent composition or sensory stimulation agent composition which contains at least one of diester compounds of dicarboxylic acid represented by the formula (1) wherein A represents CH 2 or CH═CH, n represents an integer of 0 to 4 when A is CH 2 , or 1 when A is CH═CH, B is an alcohol residue having 10 to 18 carbon atoms and containing a para-menthane skeleton, which may have a substituent, and C is an alcohol residue having 6 to 18 carbon atoms, which may have a substituent as well as a flavor or fragrance composition, a beverage, a food product, a perfume or cosmetic product, a toiletry product, daily utensil products or groceries, a fiber, a fiber product, clothes, clothing or a medicine, wherein the cooling sensation agent composition or the sensory stimulation agent composition is compounded.

  本文披露了一种包含以下化学式（1）所代表的二羧酸双酯化合物之一的冷却感剂组合物或感官刺激剂组合物，其中A代表CH2或CH═CH，n代表整数0至4（当A为CH2时）或1（当A为CH═CH时），B是含有10至18个碳原子并含有对蒎烷骨架的醇残基，可能有取代基，C是含有6至18个碳原子的醇残基，可能也有取代基，以及香料或香精组合物、饮料、食品产品、香水或化妆品产品、洗涤用品、日用品或杂货、纤维、纤维制品、衣服、服装或药品，其中复合了冷却感剂组合物或感官刺激剂组合物。
• A facile microwave-assisted Diels–Alder reaction of vinylboronates
  作者：Ariel M. Sarotti、Pablo L. Pisano、Silvina C. Pellegrinet

  DOI：10.1039/c0ob00020e

  日期：——

  The Diels–Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels–Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels–Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.

  乙烯基硼酸酯的狄尔斯-阿尔德反应可以使用微波辐射轻松进行，从而获得优异的环加合物产率。由于其对水解的稳定性、操作简单性和 Diels-Alder 产品的产率，频哪醇乙烯基硼酸酯成为首选试剂。据我们所知，这是微波辅助硼取代亲双烯体的狄尔斯-阿尔德反应的第一个例子。随后用碱性过氧化氢对环加合物进行原位氧化，有效地提供了醇。
• Evaluation of the use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of secondary cyclohexenols
  作者：Ariel M. Sarotti、Pablo L. Pisano、Silvina C. Pellegrinet

  DOI：10.3998/ark.5550190.0012.728

  日期：——

  The use of mandelate derivatives to determine the enantiomeric purity and the absolute configuration of isomeric mixtures of bicyclic and monocyclic secondary cyclohexenols was investigated. Synthesis, NMR and conformational analyses of the derivatives were performed and Gauge-Independent Atomic Orbital (GIAO) 1 H NMR Boltzmann weighted average chemical shifts were computed. The studied methodology

  研究了使用扁桃酸衍生物来确定双环和单环仲环己烯醇的异构混合物的对映体纯度和绝对构型。进行了衍生物的合成、NMR 和构象分析，并计算了与规范无关的原子轨道 (GIAO) 1 H NMR 玻尔兹曼加权平均化学位移。所研究的方法被证明对大多数所研究的系统具有实用价值。