(S)-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol | 1572476-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol
• CAS: 1572476-88-0
• 化学式: C₁₈H₁₆O₃S
• 分子量: 312.389
• InChiKey: DAHMJADGJQUGRP-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanone 在 Ru(OTf)(TsDPEN)(η6-p-cymene) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、4.05 MPa 条件下， 反应 24.0h， 以94%的产率得到(S)-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol
  参考文献：
  名称：

  手性阳离子钌二胺催化剂对β-酮磺酰胺和β-酮砜的不对称加氢反应

  摘要：

  AbstractOptically active β‐hydroxy sulfonamides and β‐hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of β‐keto sulfonamides and β‐keto sulfones has been developed using the phosphine‐free chiral ruthenium complex Ru(OTf)(TsDPEN)(η6‐p‐cymene) as the catalyst, to afford the corresponding β‐hydroxy sulfonamides and β‐hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic β‐keto sulfonamides and β‐keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic β‐hydroxy sulfonamides and β‐hydroxy sulfones in good yields with excellent enantio‐ and diastereoselectivities.magnified image

  DOI：

  10.1002/adsc.201300331

文献信息

• Highly Enantioselective One-Pot Synthesis of Chiral β-Hydroxy Sulfones via Asymmetric Transfer Hydrogenation in an Aqueous Medium
  作者：Dacheng Zhang、Tanyu Cheng、Qiankun Zhao、Jianyou Xu、Guohua Liu

  DOI：10.1021/ol502832a

  日期：2014.11.7

  A mild transformation in an aqueous medium for the one-pot synthesis of optically active β-hydroxy sulfones is described. The intermediates of β-keto sulfones obtained via a nucleophilic substitution reaction of α-bromoketones and sodium sulfinates in H2O/MeOH (1:3, v/v) at 50 °C were reduced through Ru-catalyzed asymmetric transfer hydrogenation in one-pot using HCOONa as a hydrogen source providing

  描述了在水性介质中的温和转化，用于一锅合成旋光性β-羟基砜。在50°C下通过Ru催化的不对称转移加氢还原反应，通过α-溴代酮和亚磺酸钠在H 2 O / MeOH（1：3，v / v）中的亲核取代反应获得的β-酮砜中间体使用HCOONa作为氢源的高电位锅，可提供高收率和出色的对映选择性的各种手性β-羟基砜。
• One-pot synthesis of optically pure β-hydroxy sulfones via a heterogeneous ruthenium/diamine-promoted nucleophilic substitution-asymmetric transfer hydrogenation tandem process
  作者：Jinyu Wang、Liang Wu、Xiaoying Hu、Rui Liu、Ronghua Jin、Guohua Liu

  DOI：10.1039/c7cy01262d

  日期：——

  silica-based ruthenium/diamine-functionalized heterogeneous catalyst is prepared through the co-condensation of chiral 4-((trimethoxysilyl)ethyl)phenylsulfonyl-1,2-diphenylethylene-diamine and tetraethoxysilane, followed by complexation with a ruthenium/diamine complex. Its solid-state carbon cross-polarization/magic angle spinning NMR spectrum demonstrates well-defined single-site ruthenium/diamine species

  介孔二氧化硅基钌/二胺官能化多相催化剂是通过手性4-（（三甲氧基甲硅烷基）乙基）苯基磺酰基-1，2-二苯基乙二胺与四乙氧基硅烷的共缩合反应，然后与钌/二胺配合物络合制备的。 。它的固态碳交叉极化/魔角旋转NMR光谱显示出明确定义的单中心钌/二胺物种，而扫描电子显微镜和透射电子显微镜图像证实了均匀介孔结构的纳米颗粒上钌的活性中心高度分布。这种多相催化剂在α-溴代酮和磺酸钠的亲核取代-不对称转移氢化一锅对映选择性串联反应中显示出高催化和对映选择性性能，产生各种手性β-羟基砜，对映选择性高达99％。此外，再循环的非均相催化剂可以重复使用至少六次，为在环境友好的介质中一锅法制备手性β-羟基砜提供了一种实用的方法。