(S)-(2-methylphenyl)(4'-methylphenyl)methanol | 1005216-35-2

• 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)-(2-methylphenyl)(4'-methylphenyl)methanol
• 英文别名: (S)-(2-tolyl)-(4'-tolyl)methanol；(S)-(2-tolyl)(4-tolyl)methanol；(S)-(2-methylphenyl)-(4-methylphenyl)methanol
• CAS: 1005216-35-2
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: JPLCUCRENZBAHB-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (2-methylphenyl)(4-methylphenyl)methanone 在 C₈₄H₈₀Cl₄N₂O₂P₄Ru₃ 、 氢气 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 10.0 ℃ 、4.0 MPa 条件下， 以96 %的产率得到(S)-(2-methylphenyl)(4'-methylphenyl)methanol
  参考文献：
  名称：

  RuPHOX-Ru 催化不对称氢化合成手性二芳基甲醇

  摘要：

  已经建立了 RuPHOX-Ru 催化的二芳基酮不对称氢化，以高达 99% 的产率和 99% ee 提供相应的手性二芳基甲醇。该方案可以在催化剂负载量相对较低 (2000 S/C) 的克规模上进行，所得产品可进行多种有用的转化，特别是用于手性药物的合成，例如 ( S ) -Orphenadrine和( S )-新苯二甲酸。氘标记和对照实验表明，RuPHOX-Ru 催化的不对称氢化完全以 H 2作为唯一氢源进行氢化。

  DOI：

  10.1002/adsc.202300213

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。
• Development of Asymmetric Nickel-Catalyzed Arylation of Aromatic Aldehydes with Arylboron Reagents
  作者：Kazuhiro Kondo、Toyohiko Aoyama、Kana Yamamoto、Kaori Tsurumi、Fumie Sakurai

  DOI：10.1055/s-0028-1083216

  日期：2008.11

  described. This development allowed the asymmetric nickel-catalyzed 1,2-addition of arylboron reagents to aromatic aldehydes. The enantioselectivity is synthetically acceptable (up to 81% ee) using 1-naphthaldehyde and 2-substituted aromatic aldehydes as substrates. The results have enantioselectivity comparable to the best results reported by us for the rhodium-catalyzed arylation of aromatic aldehydes.

  描述了在膦配体存在下，镍催化的三芳基环硼氧烷与芳香醛的 1,2-加成反应。这一发展允许不对称镍催化的芳基硼试剂与芳香醛的 1,2-加成。使用 1-萘醛和 2-取代芳香醛作为底物，对映选择性在合成上是可接受的（高达 81% ee）。结果的对映选择性与我们报道的铑催化芳族醛芳基化的最佳结果相当。
• Catalytic enantioselective arylation of aryl aldehydes by chiral aminophenol ligands
  作者：Xiao-Feng Yang、Takuji Hirose、Guang-You Zhang

  DOI：10.1016/j.tetasy.2009.01.025

  日期：2009.3

  The catalytic enantioselective arylation of aryl aldehydes using boronic acids as the source of transferable aryl groups is described; the reaction is found to proceed in good yields and in good to high enantioselectivities (up to 99% ee) in the presence of a chiral aminophenol ligand.

  描述了使用硼酸作为可转移的芳基基团的芳族醛的催化对映选择性芳基化。发现在手性氨基酚配体存在下，该反应以高收率和高至高对映选择性（高达99％ee）进行。
• 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.
• 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.