3-甲基-5-苯基-2-戊醇 | 36748-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲基-5-苯基-2-戊醇
• 英文名称: 3-methyl-5-phenyl-2-pentanol
• 英文别名: 3-methyl-5-phenylpentan-2-ol；α,β-dimethylbenzenebutanol；alpha,beta-Dimethylbenzenebutanol
• CAS: 36748-82-0
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: PRCGAVVRFUPYKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  乙酸乙烯酯 、 3-甲基-5-苯基-2-戊醇 在 lipase B (Candida antarctica, Chirazyme L-2)-Florisil 作用下， 反应 3.0h， 生成 (1RS,2RS)-1,2-dimethyl-4-phenylbutyl acetate 、 (2S,3S)-3-methyl-5-phenylpentan-2-ol 、 (2R,3S)-3-methyl-5-phenylpentan-2-ol 、 (1RS,2SR)-1,2-dimethyl-4-phenylbutyl acetate
  参考文献：
  名称：

  Chemoenzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-propanediol Mono(p-Methoxybenzyl Ether)

  摘要：

  In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acylation has been elaborated. Candida antarctica lipase-catalyzed hydrolysis of the corresponding racemic acetate proceeded with high enantioselectivity (E 35). During the studies, a curious phenomenon was observed, namely, that the enantioselectivity gradually declined accompanying the progress of the hydrolysis. This was due to inhibition of the enzyme-catalyzed reaction caused by the accumulation of the resultant alcohol. The rate of reaction of the more reactive enantiomer became lower. This situation prompted a new process, which would minimize the contamination or the undesired enantiomer, prior to the enzyme-catalyzed hydrolysis. This was successfully achieved with the aid of another Pseudomonas cepacia lipase-catalyzed desymmetrization, taking advantage of the prochiral nature of the starting material, 2-methyl-1,3-propanediol, and the subsequent p-methoxybenzylation under mild conditions.

  DOI：

  10.1002/1615-4169(200108)343:6/7<624::aid-adsc624>3.3.co;2-h
• 作为产物：
  描述：

  α-甲基苯丁酸 在 乙酰氯 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 3-甲基-5-苯基-2-戊醇
  参考文献：
  名称：

  氢芳烃的碳 13 磁共振。二、四氢萘和四氢蒽及其甲基衍生物的构象

  摘要：

  已获得 36 种甲基化四氢萘和四氢蒽的碳 13 化学位移数据。对明确构象的化合物的环碳进行了最小二乘回归分析，以确定两个不同脂肪族位置的甲基取代参数，结果已用于估计构象移动化合物的平衡位置。得出的结论是，1-甲基萘满在室温下以基本相同的构象异构体存在，但 2-甲基衍生物主要由具有赤道甲基的构象支配。将取代基参数与先前为甲基化环己烷确定的参数进行比较。对甲基化学位移的类似分析没有成功，部分原因是饱和环的高度柔性。

  DOI：

  10.1021/ja00350a042

文献信息

• Sustainable radical reduction through catalyzed hydrogen atom transfer reactions (CHAT-reactions)
  作者：Andreas Gansäuer、Matthias Otte、Frederik Piestert、Chun-An Fan

  DOI：10.1016/j.tet.2009.03.088

  日期：2009.6

  system with coupled catalytic cycles is described that allows radical reduction by catalyzed hydrogen atom transfer (CHAT) from transition metal hydrides. These intermediates are generated through H2 activation. Radical generation is carried out by titanocene catalyzed electron transfer to epoxides. The reaction provides a novel entry into the atom-economical reduction of radicals that has long been

  描述了具有耦合的催化循环的系统，其允许通过从过渡金属氢化物催化的氢原子转移（CHAT）进行自由基还原。这些中间体是通过H 2活化而产生的。自由基的产生是通过钛茂催化的电子转移到环氧化物上进行的。该反应为自由基的原子经济还原提供了新的途径，长期以来一直将其视为自由基化学工业应用的关键问题。
• Palladium-Catalyzed Isomerization of<i>exo</i>-Methylenic Allylic Alcohols
  作者：Paul S. Fordred、D. Gangani Niyadurupola、Richard Wisedale、Steven D. Bull

  DOI：10.1002/adsc.200900309

  日期：2009.10

  Treatment of allylic alcohols containing a 1,1-disubstituted alkene with a palladium catalyst and hydrogen gas (1 bar) results in facile isomerization to their corresponding trisubstituted (E)-allylic alcohols, along with small amounts of the corresponding hydrogenated products.

  用钯催化剂和氢气（1bar）处理含有1，1-二取代的烯烃的烯丙基醇，以及少量的相应的氢化产物，容易地异构化为它们相应的三取代的（E）-烯丙基醇。
• Friedel-Crafts cyclialkylations of certain mono- and diphenyl-substituted alcohols and alkyl chlorides
  作者：Ali Ali. Khalaf、Royston M. Roberts

  DOI：10.1021/jo00799a001

  日期：1972.7.29
• Chemoenzymatic Approach toward the Pure Enantiomers of 2-Methyl-1,3-propanediol Mono(p-Methoxybenzyl Ether)
  作者：Tomohiro Akeboshi、Yoshikazu Ohtsuka、Takashi Ishihara、Takeshi Sugai

  DOI：10.1002/1615-4169(200108)343:6/7<624::aid-adsc624>3.3.co;2-h

  日期：2001.8

  In a route towards the enantiomerically pure 2-methylpropane-1,3-diol mono(p-methoxybenzyl ether), which is an important starting material for natural product synthesis, a kinetic resolution approach by means of lipase-catalyzed hydrolysis as well as acylation has been elaborated. Candida antarctica lipase-catalyzed hydrolysis of the corresponding racemic acetate proceeded with high enantioselectivity (E 35). During the studies, a curious phenomenon was observed, namely, that the enantioselectivity gradually declined accompanying the progress of the hydrolysis. This was due to inhibition of the enzyme-catalyzed reaction caused by the accumulation of the resultant alcohol. The rate of reaction of the more reactive enantiomer became lower. This situation prompted a new process, which would minimize the contamination or the undesired enantiomer, prior to the enzyme-catalyzed hydrolysis. This was successfully achieved with the aid of another Pseudomonas cepacia lipase-catalyzed desymmetrization, taking advantage of the prochiral nature of the starting material, 2-methyl-1,3-propanediol, and the subsequent p-methoxybenzylation under mild conditions.
• Carbon-13 magnetic resonance of hydroaromatics. II. Conformation of Tetralin and tetrahydroanthracene and their methyl derivatives
  作者：Frederick G. Morin、W. James Horton、David M. Grant、Don K. Dalling、Ronald J. Pugmire

  DOI：10.1021/ja00350a042

  日期：1983.6

  Carbon-13 chemical shift data have been acquired for 36 methylated tetralins and tetrahydroanthracenes. A least-squares regression analysis has been undertaken on the ring carbons of compounds of unequivocal conformation to determine methyl substituent parameters for the two distinct aliphatic positions and the results have been used to estimate the position of equilibrium of conformationally mobile

  已获得 36 种甲基化四氢萘和四氢蒽的碳 13 化学位移数据。对明确构象的化合物的环碳进行了最小二乘回归分析，以确定两个不同脂肪族位置的甲基取代参数，结果已用于估计构象移动化合物的平衡位置。得出的结论是，1-甲基萘满在室温下以基本相同的构象异构体存在，但 2-甲基衍生物主要由具有赤道甲基的构象支配。将取代基参数与先前为甲基化环己烷确定的参数进行比较。对甲基化学位移的类似分析没有成功，部分原因是饱和环的高度柔性。