(S)-2-(benzyloxy)-2-phenyl-1-ethanol | 105581-82-6

• 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: (S)-2-(benzyloxy)-2-phenyl-1-ethanol
• 英文别名: (S)-(+)-2-benzyloxy-2-phenylethanol；(2S)-2-phenyl-2-phenylmethoxyethanol
• CAS: 105581-82-6
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: ISSNKZJYYDZTGR-OAHLLOKOSA-N

物化性质

• 沸点：
  359.9±27.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(benzyloxy)-2-phenyl-1-ethanol 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 反应 76.0h， 生成 (S)-(+)-1-苯基-1,2-乙二醇对甲苯磺酸酯
  参考文献：
  名称：

  有机锡磷酸酯缩合物催化醇与环氧乙烷的开环。在叔和苄基中心完全反转

  摘要：

  有机锡磷酸缩合物催化剂已实现手性环氧乙烷的区域和立体特异性开环。醇仅在叔和苄基位置上进攻。尽管就区域选择性而言，催化剂看似具有酸性特征，但手性中心是完全倒置的。该新方法学用于对映体纯的芳樟醇的合成，以及将市售的（R）-苯乙烯氧化物转化为（S）对应物的方法。

  DOI：

  10.1016/s0040-4020(01)88286-7
• 作为产物：
  描述：

  tert-butyl (2R)-2-[(S)-hydroxy(phenyl)methyl]-4,4-dimethyl-1,3-oxazolidine-3-carboxylate 在 sodium tetrahydroborate 、 水 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-(benzyloxy)-2-phenyl-1-ethanol
  参考文献：
  名称：

  Formation and reaction of 2-metalated N-Boc-4,4-dimethyl-1,3-oxazolidines in the presence of (−)-sparteine: new chiral formyl anion equivalents

  摘要：

  Lithiation of N-Boc-4,4-dimethyl-1,3-oxazolidine with s-BuLi and the following reaction with benzaldehyde was carried out in the presence of (-)-sparteine. The reaction was not diastereoselective (syn:anti=46:54), but each isomer of the adducts was obtained enantioselectively (syn: 90% ee, anti: 88% eel. Addition of MgBr2 to the reaction mixture increased the diastereoselectivity to syn:anti=90:10. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00319-x

文献信息

• A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes
  作者：Ankush Banerjee、Modhu Sudan Maji

  DOI：10.1002/chem.201902268

  日期：2019.9.2

  A Brønsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A

  已经开发出布朗斯台德酸催化的，操作简单的，可扩展的途径，以合成多种官能化的α-（3-吲哚基）酮，并且通过选择合适的羰基化合物消除了长期存在的区域异构问题。使用容易获得且便宜的瓶试剂作为催化剂。该方案也适用于高密度官能化的α-（3-吡咯基）酮的合成。详细的机理研究证实烯醇醚作为反应中间体。几种后合成修饰以及易于获得的β-咔啉，色胺，色胺醇和螺吲哚烯碱都证明了这种功能强大的构件的合成效用。基于这一概念，通过级联环化策略构建了功能化的咔唑。
• Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral <i>N</i>-Sulfonyl Imines
  作者：David A. Gutierrez、James Fettinger、K. N. Houk、Kaori Ando、Jared T. Shaw

  DOI：10.1021/acs.orglett.1c04219

  日期：2022.2.11

  to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon–carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers

  描述了路易斯酸促进前手性E-和Z-烯丙基亲核试剂与手性 α-烷氧基N-甲苯磺酰基亚胺的加成。烯烃几何结构选择性地转移到新形成的碳-碳键上，从而对所得 2-烷氧基-3- N-甲苯磺酰基-4-烷基-5-己烯产物的 C1、C2 和 C3 进行立体化学控制。还提出了阐明高选择性的计算分析。该方法用于合成两种天然存在的硫磺酰胺异构体。
• Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis
  作者：Martin Pawliczek、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1039/c7sc04854h

  日期：——

  Herein, we report the first alkylative kinetic resolution of vicinal alcohols realized by cooperative use of a chiral quaternary ammonium salt and an achiral borinic acid. In addition, a catalytic regioselective alkylation of a secondary alcohol in the presence of an unprotected primary one is presented, emphasizing the unique selectivity and potential of this ammonium borinate catalysis.

  在此，我们报告了通过手性季铵盐和非手性硼酸的协同使用实现的连位醇的第一次烷基化动力学拆分。此外，还介绍了在未保护的伯醇存在下仲醇的催化区域选择性烷基化，强调了这种硼酸铵催化的独特选择性和潜力。
• Asymmetric synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, and two of its stereoisomers
  作者：Kwang Youn Ko、Ernest L. Eliel

  DOI：10.1021/jo00376a056

  日期：1986.12
• One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1002/1521-3897(200009)342:7<654::aid-prac654>3.3.co;2-q

  日期：2000.9

  O-Allylations and O-benzylations of alpha -hydroxy esters (3a-3c) are performed without racemization. The reagents applied, O-allyl- and O-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.