(S)-1,4-diphenylbutan-2-ol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (S)-1,4-diphenylbutan-2-ol
• 英文别名: (2S)-1,4-diphenylbutan-2-ol
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: IJOUEDMZEULIJL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  phenethyl(p-tolyl)sulfane 在 bis(acetylacetonate)oxovanadium N-氯代丁二酰亚胺 、 双氧水 、 叔丁基锂 、 potassium carbonate 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 、 正戊烷 为溶剂， 反应 174.0h， 生成 (S)-1,4-diphenylbutan-2-ol
  参考文献：
  名称：

  Iterative Stereospecific Reagent-Controlled Homologation of Pinacol Boronates by Enantioenriched α-Chloroalkyllithium Reagents

  摘要：

  Reaction of pinacol boronates with putative enantioenriched alpha-chloroalkyllithium species, generated in situ from homochiral alpha-chloroalkylsulfoxides by sulfoxide ligand exchange with t-BuLi in PhMe at -78 degrees C, gave chain-extended boronic ester products with generally excellent stereochemical fidelity. Iteration of this stereospecific reagent-controlled homologation (StReCH) process enabled the programmed synthesis of all four stereoisomers of a stereodiad-containing model system (4-benzyl-1,6-diphenylhexan-2-ol) with er >= 97:3 in all cases.

  DOI：

  10.1021/ja068808s

文献信息

• Reagent-Controlled Asymmetric Homologation of Boronic Esters by Enantioenriched Main-Group Chiral Carbenoids
  作者：Paul R. Blakemore、Stephen P. Marsden、Huw D. Vater

  DOI：10.1021/ol053055k

  日期：2006.2.1

  and (S)-1-chloro-2-phenylethyllithium (26), generated in situ by sulfoxide ligand exchange from (-)-(R(S),R)-1-chloro-2-phenylethyl p-tolyl sulfoxide (8), effected the stereocontrolled homologation of boronic esters. sec-Alcohols derived from the product boronates by oxidation with basic hydrogen peroxide exhibited % ee closely approaching that of sulfoxide 8 in examples employing Li-carbenoid 26.

  [反应：参见正文]通过亚砜配体交换从原位生成的推定对映体富集类胡萝卜素物质（R）-1-氯-2-苯基乙基氯化镁（9）和（S）-1-氯-2-苯基乙基锂（26） （-）-（R（S），R）-1-氯-2-苯基乙基对甲苯基亚砜（8）实现了硼酸酯的立体控制同源性。在使用Li-类胡萝卜素26的实例中，通过用碱性过氧化氢氧化衍生自硼酸盐产物的仲醇所显示的ee百分数接近于亚砜8的百分数。
• Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine
  作者：Tadashi Ema、Norichika Ura、Masataka Yoshii、Toshinobu Korenaga、Takashi Sakai

  DOI：10.1016/j.tet.2009.09.058

  日期：2009.11

  We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure. and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products Could be predicted correctly in most cases (28 out of 30) (C) 2009 Elsevier Ltd All rights reserved
• Chiral vinyl dioxazaborocines in synthesis: asymmetric cuprate additions to β-boronyl acrylates and vinyl sulfones
  作者：Christopher N Farthing、Stephen P Marsden

  DOI：10.1016/s0040-4039(00)00572-4

  日期：2000.5

  The first examples of the addition of organometallic reagents to electron deficient boron-substituted olefins are reported. Thus, copper catalysed addition of Grignard reagents to chiral acryloyl and vinylsulfonyl dioxazaborocines, followed by oxidative removal of the boron, gives beta-hydroxy esters and sulfones with asymmetric inductions up to 81 and 95% ee, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration
  作者：Zhonglin Tao、Kevin A. Robb、Jesse L. Panger、Scott E. Denmark

  DOI：10.1021/jacs.8b10288

  日期：2018.11.21

  A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give exclusively anti carbosulfenylation products. A broad scope of aryl groups migrate with good yield and excellent enantioselectivity (up to 99:1 e.r.). Similarly, a range of di- and trisubstituted alkenylboronic esters are competent reaction partners. This method provides access to both secondary and tertiary chiral alkylboronic esters.