(R)-2-(4-bromophenyl)butan-2-ol | 58977-33-6

• 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)-2-(4-bromophenyl)butan-2-ol
• 英文别名: 2-(4-bromophenyl)butan-2-ol
• CAS: 58977-33-6
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: NJHFESJPVIPUEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  乙基溴化镁 、 4-溴苯乙酮 在 噻吩-2-甲酸亚铜(I) 、 C₅₀H₆₀ClNP₂ 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以72%的产率得到(R)-2-(4-bromophenyl)butan-2-ol
  参考文献：
  名称：

  W-Phos配体的合成及其在铜催化线性格氏试剂对酮选择性加成中的应用

  摘要：

  设计了一个新的 PNP 配体 ( W-Phos )家族，并将其应用于铜催化的线性格氏试剂与酮的不对称加成，从而能够以高产率和优异的对映选择性轻松获得多功能手性叔醇。

  DOI：

  10.1002/anie.202204443

文献信息

• Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative and mechanistic aspects
  作者：Beat Weber、Dieter Seebach

  DOI：10.1016/s0040-4020(01)90463-6

  日期：1994.1

  In the presence of equimolar amounts of the Mg alkoxide from α,α,α′,α′-tetraphenyl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (a TADDOL) primary Grignard reagents (Et, Pr, Bu, Oct, 3-butenyl) add to carbo- and heteroaromatic methyl ketones in THF at −100°C to give tertiary alcohols of enantiomeric excesses reaching values above 98%. The scope and limitation of the method are investigated. The reaction

  在等摩尔量的α，α，α'，α'-四苯基-2,2-二甲基-1,3-二氧戊环-4,5-二甲醇（TADDOL）伯碱试剂（Et， Pr，Bu，Oct，3-丁烯基）在-100°C下加到THF中的碳和杂芳族甲基酮中，得到对映体过量的叔醇，其值超过98％。研究了该方法的范围和局限性。在剧烈搅拌的非均质混合物中发生的反应在没有反应中心的空间位阻的情况下提供了最佳结果。由烷基溴制得的格氏试剂优于由氯化物制得的试剂。TADDOL的ee与2-苯基-2-癸醇的产品的ee之间存在完美的线性关系；那些大专绝对构型已知的醇是由酮羰基的Re面通过亲核攻击形成的。讨论了反应的立体化学过程的三种暂定机理模型。
• Asymmetric addition of Grignard reagents to ketones: culmination of the ligand-mediated methodology allows modular construction of chiral tertiary alcohols
  作者：Claudio Monasterolo、Ryan O'Gara、Saranna E. Kavanagh、Sadbh E. Byrne、Bartosz Bieszczad、Orla Murray、Michael Wiesinger、Rebecca A. Lynch、Kirill Nikitin、Declan G. Gilheany

  DOI：10.1039/d1sc06350b

  日期：——

  A new class of biaryl chiral ligands derived from 1,2-diaminocyclohexane (1,2-DACH) has been designed to enable the asymmetric addition of aliphatic and, for the first time, aromatic Grignard reagents to ketones for the preparation of highly enantioenriched tertiary alcohols (up to 95% ee). The newly developed ligands L12 and L12′ together with the previously reported L0 and L0′ define a set of complementary

  一种新的衍生自 1,2-二氨基环己烷 (1,2-DACH) 的联芳基手性配体已被设计用于将脂肪族和芳香族格氏试剂不对称加成到酮中，以制备高度对映体富集的叔酒精（高达 95% ee）。新开发的配体L12和L12'以及先前报道的L0和L0'定义了一组互补的手性启动子，它提供了对各种结构多样的非外消旋叔醇的模块化结构的访问，具有挑战性的季立体中心。目前的进展通过将范围扩展到芳族有机镁试剂来完成我们的不对称格氏方法，同时由于改进的合成路线可以直接获得手性配体而促进其在有机合成中的实施。该方法的合成效用已通过通过中间体 ( R ) -3a开发一种新型的、高度对映选择性的正式合成抗组胺药 API clemastine 得到证明. 利用格氏合成提供的 3-断开方法的力量，( R )- 3a与配体 ( R , R )- L12以 94% 的 ee 获得。本文描述的工作标志着我们为手性叔醇的不对称格氏合成建
• First enantioselective addition of diethylzinc and dimethylzinc to prostereogenic ketones catalysed by camphorsulfonamide-titanium alkoxide derivatives
  作者：Diego J Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(98)00236-1

  日期：1998.5

  The reaction of diethylzinc or dimethylzinc with prostereogenic ketones, in the presence of a stoichiometric amount of titanium tetraisopropoxide and a catalytic amount (20%) of camphorsulfonamide derivatives as chiral ligands leads to the formation of the corresponding enantioenriched tert-alcohols with enantiomeric ratios up to 94.5 : 5.5. The best results were obtained when phenones are used as substrates independently of the dialkylzinc reagent. The enantioselectivity shows a linear relationship with the enantiomeric excess of the ligand and seems to be independent of the reaction yield. A tentative catalytic cycle and mechanistic model are proposed for this new reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Weber, Beat; Seebach, Dieter, Angewandte Chemie, 1992, vol. 104, # 1, p. 96 - 97
  作者：Weber, Beat、Seebach, Dieter

  DOI：——

  日期：——
• Toward the continuous-flow synthesis of chiral tertiary alcohols by enantioselective addition of organozinc reagents to ketones using nanosize isoborneol ligands
  作者：Vicente J. Forrat、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tetasy.2008.02.002

  日期：2008.3

  The catalytic enantio selective addition of different organozinc reagents, such as alkyl or in situ generated phenylzinc derivatives to simple aryl ketones, was accomplished using titanium tetraisopropoxide and chiral ligands derived from trans-1-arenesulfonylamino-2-isoborneolsulfonylamidocyclohexane and Frechet-type dendrons with up to 2.5 nin of diameter, giving the corresponding tertiary alcohols with enantioselectivities up to >99%. A simple and efficient procedure for the synthesis of the ligands used is also described, involving the radical addition of the corresponding thiol dendron to the chiral styryl-isoborneol derivative. (C) 2008 Elsevier Ltd. All rights reserved.