(S)-(4-chlorophenyl)-(2'-methylphenyl)methanol

• 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: (S)-(4-chlorophenyl)-(2'-methylphenyl)methanol
• 英文别名: (S)-(4-chlorophenyl)(2'-methylphenyl)methanol；(S)-(p-chlorophenyl)(o-tolyl)methanol；(4-chlorophenyl)(2-tolyl)methanol；(S)-(4-chlorophenyl)-(2-methylphenyl)methanol
• 化学式: C₁₄H₁₃ClO
• 分子量: 232.71
• InChiKey: QWNMGIKDLZTPOI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tri-o-tolylboroxine 、 4-氯苯甲醛 在 diethylzinc 、 (2R,3S,3aS,4aR,6R,8aS)-2-isopropyl-6,9,9-trimethyl-3-phenyldecahydro-4aH-pyrrolo[2,1-b][1,3]benzoxazin-3-ol 作用下， 以 甲苯 为溶剂， 反应 0.75h， 生成 (4-chlorophenyl)(2-tolyl)methanol 、 (S)-(4-chlorophenyl)-(2'-methylphenyl)methanol
  参考文献：
  名称：

  Asymmetric additive-free aryl addition to aldehydes using perhydrobenzoxazines as ligands and boroxins as aryl source

  摘要：

  报道了一种高效的对映选择性芳基加成反应，利用硼氧烷作为芳基来源，并采用构象限制的过氢-1,3-苯并呋喃作为配体。通过合理组合硼氧烷和芳香醛，使用相同的配体可以获得手性芳基苯甲醇和1,1′-二取代二芳基甲醇的两种对映体，具有优异的产率和对映选择性。即使在有取代的硼氧烷存在时，对映控制也不受电子效应或空间位阻的显著影响。当使用取代芳基硼氧烷时，可以达到非常均匀的对映体过量，并且无需任何类型的添加剂或预处理。

  DOI：

  10.1039/c1ob05717k

文献信息

• Evaluation of Enantiopure <i>N</i>-(Ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol for Catalytic Asymmetric Addition of Organozinc Reagents to Aldehydes
  作者：Min-Can Wang、Qing-Jian Zhang、Wen-Xian Zhao、Xiao-Dan Wang、Xue Ding、Tao-Tao Jing、Mao-Ping Song

  DOI：10.1021/jo701943x

  日期：2008.1.1

  catalytic asymmetric addition of organozinc reagents to aldehydes. The asymmetric ethylation, methylation, arylation, and alkynylation of aldehydes achieved enantioselectivity of up to 98.4%, 94.1%, 99.0%, and 84.6% ee, respectively, in the presence of a catalytic amount of chiral N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol. Our results demonstrated further that the four-membered heterocycle-based

  从廉价且容易获得的1 -（+）-甲硫氨酸开发了一种简便实用的对映体纯的N-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇的制备方法。合成亮点包括手性氮杂环丁烷环的三步，一锅结构和一种改进的单步过程为关键中间体的合成的发展升-2-氨基-4-溴丁酸。对映纯N评估了-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇催化有机锌试剂向醛的催化不对称加成。在催化量的手性氮存在下，醛的不对称乙基化，甲基化，芳基化和炔基化分别实现了高达98.4％，94.1％，99.0％和84.6％ee的对映选择性。-（二茂铁基甲基）氮杂环丁烷-2-基（二苯基）甲醇。我们的结果进一步证明，基于四元杂环的骨架是催化不对称诱导反应的良好潜在手性单元，与苯基相比，笨重的二茂铁基的阻碍在对映选择性中发挥了重要作用。基于包括两个HOAc分子的手性配体3b的晶体结构和先前的研究，已经提出了催化不对称加成的可能过渡。
• Diarylmethanols by Catalyzed Asymmetric Aryl Transfer Reactions onto Aldehydes Using Boronic Acids as Aryl Source
  作者：Frank Schmidt、Jens Rudolph、Carsten Bolm

  DOI：10.1002/adsc.200600390

  日期：2007.3.5

  Using a planar-chiral ferrocene as catalyst and combinations of functionalized aldehydes and substituted arylboronic acids as starting materials, asymmetric aryl transfer reactions give access to structurally diverse, optically active diarylmethanols in high yields and enantioselectivities.

  使用平面手性二茂铁作为催化剂，并结合官能化的醛和取代的芳基硼酸作为起始原料，不对称的芳基转移反应可以以高收率和对映选择性获得结构多样的旋光性二芳基甲醇。
• A chiral Rh–phosphite complex displaying high activity in the enantioselective Rh-catalyzed addition of arylboronic acids to carbonyl compounds: when and why atropos is better than tropos
  作者：Varsha R. Jumde、Sarah Facchetti、Anna Iuliano

  DOI：10.1016/j.tetasy.2010.11.009

  日期：2010.12

  The use of deoxycholic acid derived tropos and atropoisomeric phosphites as chiral ligands in the Rh-catalyzed enantioselective addition of arylboronic acids to arylaldehydes and 2,2,2-trifluoroacetophenone is presented. Screening of these phosphites showed the high activity of the Rh-complex obtained starting from one of the two atropoisomeric ligands, which afforded complete conversion of the carbonyl compounds in short reaction times under mild reaction conditions and with ee's of up to 84%. A study aimed at getting information about the different behavior of tropos and atropoisomeric ligands is also reported. (C) 2010 Elsevier Ltd. All rights reserved.
• From Aryl Bromides to Enantioenriched Benzylic Alcohols in a Single Flask: Catalytic Asymmetric Arylation of Aldehydes
  作者：Jeung Gon Kim、Patrick J. Walsh

  DOI：10.1002/anie.200600741

  日期：2006.6.19
• Catalytic asymmetric aryl transfer: highly enantioselective preparation of (R)- and (S)-diarylmethanols catalyzed by the same chiral ferrocenyl aziridino alcohol
  作者：Min-Can Wang、Xiao-Dan Wang、Xue Ding、Zhi-Kang Liu

  DOI：10.1016/j.tet.2008.01.040

  日期：2008.3

  Highly enantioselective arylations of arylaldehydes using arylboronic acids as aryl resource were realized in the presence of a catalytic amount of (2S)-1-ferrocenylmethylaziridin-2-yl(diphenyl)methanol. In addition, the R or S enantiomers of a series of given diarylmethanols can be easily obtained in high yields with excellent enantioselectivities simply by the reverse combinations of both reaction partners. A possible transition state for the catalytic asymmetric addition has been proposed on the basis of previous studies. (c) 2008 Published by Elsevier Ltd.