(1R*,2S*)-2-(2,4,6-trimethylphenyl)cyclohexanol | 112383-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R*,2S*)-2-(2,4,6-trimethylphenyl)cyclohexanol
• 英文别名: (-)-trans-2-mesitylcyclohexan-1-ol；(+/-)-trans-2-Mesitylcyclohexanol；(+)-trans-2-Mesitylcyclohexanol；(-)-trans-2-Mesitylcyclohexanol；trans-2-mesitylcyclohexanol；(1R,2S)-2-(2,4,6-trimethylphenyl)cyclohexan-1-ol
• CAS: 112383-47-8；127215-50-3；127304-93-2；127304-94-3
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: DGNWPCYLYBGOJB-ZIAGYGMSSA-N

物化性质

• 熔点：
  76.5 °C
• 沸点：
  352.2±31.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (1R*,2S*)-2-(2,4,6-trimethylphenyl)cyclohexanol 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、106.66 Pa 条件下， 反应 4.0h， 生成 1,3,5-trimethyl-2-[(1S,2R)-2-[(1E)-2-methylbuta-1,3-dienoxy]cyclohexyl]benzene
  参考文献：
  名称：

  Asymmetrische Diels-Alder-Reaktionen von chiralen Isoprenylethern mit reaktiven Dienophilen

  摘要：

  手性异戊烯基醚与反应性二烯烃的不对称 Diels-Alder 反应 手性醇 2 与 3-乙氧基-2-甲基丙烯醛 (1) 反应生成手性 3-烷氧基-2-甲基丙烯醛 3，然后通过 Wittig 甲烯化反应生成手性异戊烯基醚 5，收率很高。1,3-二烯 5 与马来酸酐（6）或 4-苯基-4H-1,2,4-三唑-3,5-二酮（PTAD，8）等活性二烯烃发生[4+2]环加成反应，得到手性环加成物 7 和 9，收率中等至良好，非对映过量。报告了反式-2-甲苯甲基环己醇 2d 外消旋醇的解析。

  DOI：

  10.1055/s-1989-27405
• 作为产物：
  描述：

  trans-2-mesitylcyclohexyl acetate 在 phosphate buffer 作用下， 以 乙醚 为溶剂， 反应 288.0h， 以84%的产率得到(1R*,2S*)-2-(2,4,6-trimethylphenyl)cyclohexanol
  参考文献：
  名称：

  Basavaiah, Deevi; Krishna, Peddinti Rama, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 131 - 134

  摘要：

  DOI：

文献信息

• Efficient Approaches to the Stereoselective Synthesis of Chiral 2-Alkoxydienes and Heterodienes
  作者：José Barluenga、Miguel Tomás、Luis A. López、Angel Suárez-Sobrino

  DOI：10.1055/s-1997-1294

  日期：1997.8

  Three approaches to dienes having a chiral alkoxy group at C-2 are shown. Alkoxypropenylphosphonium salts 3 undergo stereoselective Wittig reaction affording high yields of racemic and/or homochiral 2-menthyloxy-, 2-(8-phenylmenthyloxy)-, 2-trans-phnylcyclohexyloxy- and 2-trans-mesitylcyclohexyloxybuta-1,3-dienes 5a-j (Method A). Esters derived from chiral alcohols 6 are methylenated with dimethyltitanocene to yield chiral dienes 5a, e, 7 (Method B). Chiral α-alkoxyacroleins 8 are prepared by the aza-Wittig reaction of 3 followed by imine hydrolysis and utilized for synthesizing various types of activated chiral alkoxycarbodienes 10, 12 and 14 (Method C), as well as 3-alkoxy-1-azabutadiene derivatives 15.

  图示了三种在C-2位具有手性烷氧基团的二烯烃合成方法。烷氧基丙烯基膦盐3经过立体选择性的Wittig反应，以高产率得到外消旋或均旋的2-薄荷氧基-、2-(8-苯基薄荷氧基)-、2-反-苯基环己氧基-和2-反-苯基二甲苯环己氧基丁a-1,3-二烯5a-j（方法A）。由手性醇6衍生的酯通过二甲基钛茂进行亚甲基化反应，生成手性二烯烃5a、e和7（方法B）。手性α-烷氧基丙烯醛8通过3的Aza-Wittig反应，接着进行亚胺水解反应制备，并用于合成多种类型的活化手性烷氧基碳二烯10、12和14（方法C），以及3-烷氧基-1-氮杂丁二烯衍生物15。
• Boron fluoride promoted opening of epoxides by organocopper and cuprate reagents
  作者：A. Alexakis、D. Jachiet、J.F. Normant

  DOI：10.1016/s0040-4020(01)88165-5

  日期：1986.1

  BF3 the reaction rate of organocopper and cuprate reagents with poorly reactive epoxides is dramatically enhanced. Lithium organocuprates are the best choice among the various organocopper and cuprate reagents tested. Even the dimesityl cyanocuprate is able to react with cyclohexene oxide in excellent yield. No products of cationic rearrangements are observed. The reaction with various epoxides shows

  在BF 3的存在下，有机铜和铜酸盐试剂与反应性较弱的环氧化物的反应速率大大提高。有机铜锂是测试的各种有机铜和铜酸盐试剂中的最佳选择。甚至氰基二甲双胍也能够以优异的产率与环己烯氧化物反应。没有观察到阳离子重排的产物。与各种环氧化物的反应显示出完全的立体化学（纯粹的防开裂）和区域化学控制（在环氧化物受阻较小的一侧发生的攻击）。
• Chiral 2-alkoxy-1,3-butadienes: synthesis and face-selectivity in Diels–Alder reactions
  作者：José Barluenga、Miguel Tomás、Angel Suárez-Sobrino、Luis A. López

  DOI：10.1039/c39950001785

  日期：——

  Chiral 2-alkoxy-1,3-butadienes are prepared from chiral alcohols, prop-2-ynyltriphenylphosphonium bromide and aldehydes; they undergo [4 + 2] cycloadditions to carbo- and hetero-dienophiles with moderate to high face-selectivity.

  手性 2-烷氧基-1,3-丁二烯由手性醇类、丙-2-炔基三苯基溴化鏻和醛类制备而成；它们与碳水化合物和杂二烯烃发生[4 + 2]环加成反应，具有中等到较高的面选择性。
• Investigating the π-Facial Discrimination Phenomenon in the Conjugate Addition of Amines to Chiral Crotonates:  A Convenient Basis for the Rational Design of Chiral Auxiliaries
  作者：Françoise Dumas、Brahim Mezrhab、Jean d'Angelo、Claude Riche、Angèle Chiaroni

  DOI：10.1021/jo951414r

  日期：1996.1.1

  This paper is concerned with the nature of the chiral inducer in the high pressure-induced conjugate addition of amines to auxiliary-tethered crotonates. Almost complete stereocontrol was obtained in the addition of diphenylmethanamine to crotonates derived from the ''arylmenthol'' auxiliaries 18a, 18c, and 4 bearing an o-methoxyphenyl, p-phenoxyphenyl, or beta-naphthyl substituent, respectively. This high efficiency has been attributed to the predominance of stacked conformations in such crotonates, a hypothesis supported by the H-1 NMR spectra, calculated energy of conformational optima of the corresponding crotonates, and X-ray crystal structure of 5a. The arene and enoate appendages are roughly coplanar, separated by 3.4-4 Angstrom. In contrast, only moderate selectivities could be achieved using various trans-2-arylcyclohexanols (27, 28, 2c, 29) as auxiliaries. In these cases the efficiency appears to be seriously compromised by the ''widening V'' arrangement exhibited by the two pi-systems, as shown in the X-ray crystal structures of crotonates 5 h and 5 k. The sense of stereochemical induction of this conjugate addition has been determined by condensing diphenylmethanamine with enantiopure crotonate (+)-5a. The adduct 9a was converted to amino alcohol (S)-11, of known configuration. This correlation is consistent with the preferential attack of the amine to the less sterically hindered enoate pi-face of(+)-5a, in its s-trans conformation. Finally, the stereochemistry of the proton transfer was determined by adding N,N-dideuteriodiphenylmethanamine to crotonate (+/-)-5a. The stereochemical outcome of this addition is consistent with the anti-addition of the incoming nitrogen nucleophile and the deuterium atom.
• Enzymatic resolution of trans-2-arylcyclohexan-1-ols using crude chicken liver esterase (CCLE) as biocatalyst
  作者：Deevi Basavaiah、Polisetti Dharma Rao

  DOI：10.1016/s0957-4166(00)86177-7

  日期：1994.1

  Homochiral trans-2-arylcyclohexan-1-ols were synthesized via crude chicken liver esterase (CCLE) mediated enantioselective hydrolysis of the corresponding racemic acetates.