(S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol | 94199-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol
• 英文别名: (2S)-2-phenyl-2-tetrahydropyran-2-yloxyethanol；(2S)-2-(oxan-2-yloxy)-2-phenylethanol
• CAS: 94199-20-9
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: BCDVRNCZMZEOBT-PZORYLMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 为溶剂， 生成 (S)-2-mercapto-1-phenylethanol
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of enantiopure 1-methoxy-3-(phenyl-2-hydroxyethylsulfinyl)-1,3-butadienes

  摘要：

  Enantiopure 1-methoxy-3-(1-phenyl- and 2-phenyl-2-hydroxyethylsulfinyl)-1,3-butadienes were prepared from ethyl maudelate. Diets-Alder reactions with methyl acrylate proceeded with complete regioselectivity and high diastereoselectivity.

  DOI：

  10.1016/s0957-4166(00)86232-1
• 作为产物：
  描述：

  D-扁桃酸 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol
  参考文献：
  名称：

  Asymmetric radical reaction in the coordination sphere. 2. Asymmetric addition of alkane- and arenesulfonyl chlorides to olefins catalyzed by a ruthenium(II)-phosphine complex with chiral ligands

  摘要：

  DOI：

  10.1021/jo00391a025

文献信息

• Zirconium cation coordination in the borohydride-mediated synthesis of β-hydroxy-N-alkoxylamines
  作者：David R Williams、John W Benbow、Thomas R Sattleberg、David C Ihle

  DOI：10.1016/s0040-4039(01)01862-7

  日期：2001.12

  Hydride reductions of oxime ethers to hydroxylamine derivatives are facilitated by the participation of neighboring hydroxyl groups. Precomplexation with zirconium cation in ether–methylene chloride solutions is effective for selective CN bond reduction. The course for stereochemical control is dictated by Lewis acid coordination complexes of E- and Z-oximino ethers which lead to the preferred diastereofacial

  邻近羟基的参与促进了肟醚的氢化物还原为羟胺衍生物。在乙醚-二氯甲烷溶液中与锆阳离子进行预络合可有效地选择性还原CN键。立体化学控制的过程由E-和Z-肟基醚的路易斯酸配位配合物决定，这导致优选的非对映体外部氢化物传递。
• Preparation of homochiral azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
  作者：Koichiro Naemura、Kazuko Ogasahara、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(96)00472-7

  日期：1997.1

  Enantiomerically pure azophenolic crown ethers 1–4 containing (S)- or (R)-1-phenylethane-1,2-diol moieties and (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol moiety as a chiral subunit were prepared; crown ethers (S,S,S,S)-1 showed high chiral recognition behaviour in complexation with 2-substituted 2-aminoethanol derivatives.

  对映体纯的偶氮酚冠醚1-4，含有（S）-或（R）-1-苯基乙烷-1,2-二醇部分和（2 S，4 S）-2,4-二甲基-3-氧杂戊烷-1,5制备了作为手性亚基的-二醇部分；冠醚（S，S，S，S）-1在与2-取代的2-氨基乙醇衍生物络合中显示出高手性识别行为。
• Preparation of homochiral phenolic crown ethers containing para-substituted phenol moiety and chiral subunits derived from (S)-1-phenylethane-1,2-diol: their chiral recognition behaviour in complexation with neutral amines
  作者：Koichiro Naemura、Yasushi Nishikawa、Junichi Fuji、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/s0957-4166(97)00047-5

  日期：1997.3

  Crown ethers 1–6 containing two chiral subunits derived from (S)-1-phenylethane-1,2-diol and a phenol moiety bearing an intra-annular OH group and an additional para-substituent have been prepared in enantiomerically pure forms and their enantiomer recognition behaviour in complexation with neutral amines has been examined by the 1H n.m.r. spectroscopic method.

  已制备对映体纯形式的冠醚1-6，它们含有两个衍生自（S）-1-苯基乙烷-1,2-二醇的手性亚基和一个带有环内OH基的酚部分以及一个额外的对位取代基，通过1 H nmr光谱法检查了与中性胺络合时对映体的识别行为。
• Enantioselective protonation of samarium enolates derived from α-heterosubstituted ketones and lactone by SmI2-mediated reduction
  作者：Yutaka Nakamura、Seiji Takeuchi、Yoshiaki Ohgo、Makoto Yamaoka、Akihiro Yoshida、Koichi Mikami

  DOI：10.1016/s0040-4020(99)00143-x

  日期：1999.4

  SmI2-mediated reductive cleavage of α-hetero substituents of α-alkyl or α-aryl ketones and lactone gave the corresponding “thermodynamic samarium enolates”. Enantioselective protonation of the samarium enolates with C2-symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.

  SmI 2介导的α-烷基或α-芳基酮的α-杂取代基和内酯的还原裂解产生相应的“热力学sa烯醇盐”。用C 2对称手性二醇对烯醇盐进行对映选择性质子化，可得到中等至高对映选择性的相应酮和内酯。
• Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines 1
  作者：Kazuko Ogasahara、Keiji Hirose、Yoshito Tobe、Koichiro Naemura

  DOI：10.1039/a703452k

  日期：——

  With (2S,4S)-2,4-dimethyl-3-oxapentane-1,5-diol and (S)- or (R)-1-phenylethane-1,2-diol as chiral subunits, optically active azophenolic crown ethers (S,S,S,S)-1, (R,S,S,R)-2, (S,S,S,S)-3 and (R,S,S,R)-4 possessing two phenyl and two methyl substituents together with the p-(2,4-dinitrophenylazo)phenol moiety have been prepared in enantiomerically pure forms. Temperature-dependent enantiomer selectivity in the complexation of these crown ethers with chiral amines has been studied by the UV–visible spectroscopic method in chloroform and from the observed association constants, thermodynamic parameters for the complexation have been calculated.

  采用(2S,4S)-2,4-二甲基-3-氧戊烷-1,5-二醇和(S)-或(R)-1-苯乙烷-1,2-二醇作为手性子单元，合成了具有两个苯基和两个甲基取代基以及p-(2,4-二硝基苯基偶氮)酚基团的光学活性偶氮酚类冠醚(S,S,S,S)-1、(R,S,S,R)-2、(S,S,S,S)-3和(R,S,S,R)-4，并且这些化合物以对映体纯形式制备。通过在氯仿中采用紫外-可见光光谱法研究了这些冠醚与手性胺的复合过程中温度依赖的对映选择性，并根据观察到的结合常数计算了复合的热力学参数。