(R)-(p-chlorophenyl)phenylmethyl acetate | 501427-14-1

• 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: (R)-(p-chlorophenyl)phenylmethyl acetate
• 英文别名: (R)-p-chlorophenyl phenyl methanol acetate ester；(R)-4-chlorobenzhydrol acetate；(R)-(4-chlorophenyl)(phenyl)methyl acetate；[(R)-(4-chlorophenyl)-phenylmethyl] acetate
• CAS: 501427-14-1
• 化学式: C₁₅H₁₃ClO₂
• 分子量: 260.72
• InChiKey: FLBMKFDKDSWBQG-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(p-chlorophenyl)phenylmethyl acetate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以18 g的产率得到(R)-4-氯二苯基甲醇
  参考文献：
  名称：

  신규한 Ｌ-클로페라스틴의 중간체 및 그 제조 방법

  摘要：

  该专利涉及一种药用价值高的L-克洛佩拉斯汀（cloperastine）的新型中间体及其制备方法，更详细地说，涉及具有以下化学结构1的L-克洛佩拉斯汀中间体以及利用酶进行立体选择性合成的方法。化学结构1中，R代表C1~C3的烷基基团。

  公开号：

  KR101510637B1
• 作为产物：
  描述：

  二苯锌 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 (R)-3,3'-bis(2'',4''-dihexyloxyphenyl)-1,1'-binaphthol 、 diethylzinc 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 (R)-(p-chlorophenyl)phenylmethyl acetate
  参考文献：
  名称：

  From Highly Enantioselective Monomeric Catalysts to Highly Enantioselective Polymeric Catalysts:  Application of Rigid and Sterically Regular Chiral Binaphthyl Polymers to the Asymmetric Synthesis of Chiral Secondary Alcohols

  摘要：

  A 1,1'-binaphthyl-based polymeric chiral catalyst with the most general enantioselectivity for the alkylzinc addition to a broad range of aldehydes has been obtained. This polymer can be easily recovered, and the recycled polymer shows the same catalytic properties as the original polymer. A highly enantioselective catalytic diphenylzinc addition to aldehydes has also been achieved by using the chiral binaphthyl monomer and polymer catalysts. Particularly, the excellent enantioselectivity observed for the addition of diphenylzinc to aromatic aldehydes allows the preparation of optically active diaryl carbinols that are synthetically useful but difficult to access by asymmetric catalysis. A novel asymmetric reduction of ketones catalyzed by the mono- and polybinaphthyl zinc complexes has been discovered. Our work on the asymmetric organozinc addition to aldehydes and the asymmetric reduction of ketones catalyzed by the zinc complexes of chiral binaphthyl monomer (R)-12 and polybinaphthyl (R)-43 has not only provided new methods to prepare optically active secondary alcohols but also demonstrated that incorporation of an enantioselective monomeric catalyst into a rigid and sterically regular polymer structure could almost completely preserve the catalytic properties of the monomeric catalyst. This strategy may find general application in converting existing highly enantioselective monomer catalysts into polymer catalysts of similar enantioselectivity provided that the catalytically active species of the monomer catalysts contain only the monomeric units rather than the aggregates of the monomers. By using this strategy, it is possible to overcame the drawbacks associated with the traditional approach to preparing polymeric chiral catalysts where the microenvironments of the catalytic sites in the polymers are often significantly altered from those in the monomeric catalysts due to the flexible and sterically irregular polymer chains.

  DOI：

  10.1021/jo990992v

文献信息

• Alkylation of Active Methylenes via Benzhydryl Cations
  作者：Giovanni Poli、Fabrice Bisaro、Guillaume Prestat、Maxime Vitale

  DOI：10.1055/s-2002-34884

  日期：——

  The acid mediated reaction between active methylenes and benzhydryl alcohols, or their derivatives, is reported. Ethyl acetoacetate, acetylacetone, and N,N-dibenzyl-malonamic acid methyl ester are benzhydrylated in quantitative yields in the presence of molar amounts of BF 3 .OEt 2 in CH 2 Cl 2 at r.t. TMSOTf and H 2 SO 4 appear to be equally efficient. Use of benzhydryl acetate in place of the starting

  报道了活性亚甲基和二苯甲醇或其衍生物之间的酸介导反应。在室温下 CH 2 Cl 2 中存在摩尔量的 BF 3 .OEt 2 时，乙酰乙酸乙酯、乙酰丙酮和 N,N-二苄基-丙二酸甲酯以定量产率二苯甲基化。 TMSOTf 和 H 2 SO 4 似乎是相同的高效的。使用乙酸二苯甲酯代替起始游离醇可以将路易斯酸降低到催化量。介绍了这种几乎没有研究的 CC 键形成的一般机制。由于醇相对于卤化物更容易获得，该方法可以与更经典的基于卤化物的碱性条件进行比较。
• A novel lipase enzyme panel exhibiting superior activity and selectivity over lipase B from Candida antarctica for the kinetic resolution of secondary alcohols
  作者：Maeve O’Neill、Denis Beecher、David Mangan、Andrew S. Rowan、Agnieszka Monte、Stefan Sroka、Jan Modregger、Bhupinder Hundle、Thomas S. Moody

  DOI：10.1016/j.tetasy.2012.03.013

  日期：2012.4

  A novel, commercially available lipase enzyme panel performing kinetic bioresolutions of a number of secondary alcohols is reported. The secondary alcohols that have been chosen are known from the literature to be particularly challenging substrates to resolve. Following initial screening, four co-solvents were investigated for each lead enzyme in an effort to assess their tolerance to common organic solvents. The superiority of these novel enzymes over lipase B from Candida antarctica (CALB) has been demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.
• Kinetic resolution of diarylmethanols using a mutated variant of lipase CALB
  作者：Karin Engström、Michaela Vallin、Karl Hult、Jan-E. Bäckvall

  DOI：10.1016/j.tet.2012.06.040

  日期：2012.9

  An enzymatic kinetic resolution of diarylmethanols via acylation has been developed. This was achieved by the use of a mutated variant of CALB that accepts larger substrates compared to the wild type. By the use of diarylmethanols with two differently sized aryl groups, enantioselective transformations were achieved. A larger size-difference led to a higher enantioselectivity. In addition, substrates with electronically different aryl groups, such as phenyl and pyridyl, also gave an enantioselective reaction. The highest E value was observed with a substrate where steric and electronic effects were combined. (C) 2012 Elsevier Ltd. All rights reserved.