(R)-(-)-2-phenyl-2-(tetrahydropyranyloxy)ethanol | 109428-31-1

• 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: (R)-(-)-2-phenyl-2-(tetrahydropyranyloxy)ethanol
• 英文别名: (R)-2-phenyl-2-(tetrahydropyran-2-yloxy)ethanol；(R)-2-phenyl-2-(3,4,5,6-tetrahydro-[2H]-pyran-2-yloxy)ethanol；(2R)-2-(oxan-2-yloxy)-2-phenylethanol
• CAS: 109428-31-1
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: BCDVRNCZMZEOBT-UEWDXFNNSA-N

物化性质

• 沸点：
  360.1±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

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：

  (R)-(-)-2-phenyl-2-(tetrahydropyranyloxy)ethanol 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 (1R)-2-[(Z)-1-(furan-2-yl)ethylideneamino]oxy-1-phenylethanol
  参考文献：
  名称：

  硼氢化物介导的β-羟基-N-烷氧基胺合成中的锆阳离子配位

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(01)01862-7
• 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 、 苯 为溶剂， 反应 94.0h， 生成 (R)-(-)-2-phenyl-2-(tetrahydropyranyloxy)ethanol
  参考文献：
  名称：

  带有一氟甲基的旋光性结构单元的合成

  摘要：

  已经进行了通过相应的乙酸酯的微生物水解制备的具有一氟甲基的旋光分子的合成工具的研究。确定这些单氟甲基化的手性化合物的绝对构型。

  DOI：

  10.1016/s0022-1139(00)81995-8

文献信息

• Acetalsulfonate derivative, process for producing the same, and process for producing styrene oxide derivative
  申请人：Mitsubishi Rayon Co., Ltd.

  公开号：US06642395B1

  公开（公告）日：2003-11-04

  There are provided an acetalsulfonate derivative useful as an intermediate for medicines and agricultural chemicals, a process for industrially producing the derivative, and a process for industrially producing a styrene oxide derivative from the acetalsulfonate derivative or from a mandelic acid derivative. A process for producing an acetalsulfonate derivative which comprises a first step of esterifying a mandelic acid derivative to form a mandelic ester derivative, a second step of protecting the mandelic ester derivative by an acetal to form an acetal derivative, a third step of reducing the acetal derivative to form an ethanediol derivative and a fourth step of reacting the ethanediol derivative with a sulfonyl chloride derivative. A process for producing a styrene oxide derivative which comprises a deprotecting step of deacetalizing the acetalsulfonate derivative and a step of epoxidizing the sulfonate derivative obtained in the deprotecting step with the aid of a base catalyst.

  提供了一种醛基磺酸酯衍生物，可用作药品和农药的中间体，以及用于工业生产该衍生物的工艺，以及用于从醛基磺酸酯衍生物或苯甲酸衍生物中工业生产苯乙烯环氧衍生物的工艺。生产醛基磺酸酯衍生物的工艺包括以下步骤：第一步，将苯甲酸衍生物酯化以形成苯甲酸酯衍生物；第二步，通过缩醛将苯甲酸酯衍生物保护以形成缩醛衍生物；第三步，还原缩醛衍生物以形成乙二醇衍生物；第四步，将乙二醇衍生物与磺酰氯衍生物反应。生产苯乙烯环氧衍生物的工艺包括脱保护步骤，即去缩醛化醛基磺酸酯衍生物，并在去保护步骤中使用碱催化剂使磺酸酯衍生物环氧化。
• 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 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。
• Compositions and methods for separating amines and amino acids from their counter-enantiomers
  申请人：——

  公开号：US20040132998A1

  公开（公告）日：2004-07-08

  Diketo- and pyridine-containing chiral crown ligands having at least two chiral bulky groups attached to two different chiral carbon atoms of the crown that are covalently bonded to or coated on suitable solid supports, and further coated by hydrophobic organic solvents are disclosed. These compositions and associated methods are characterized by selectivity of several target amine or amino acid enantiomers over their counter-enantiomers and derivatives. The composition preferably has an &agr;-value greater than or equal to 4. This allows for the separation of such enantiomers with non-chromatographic resin bed separations of three separation stages or less.

  本发明揭示了至少具有两个手性笨重基团附着在皇冠的两个不同手性碳原子上的含二酮和吡啶的手性冠配体，这些基团与适当的固体支持体共价键合或涂覆，并进一步被疏水有机溶剂涂覆。这些组合物和相关方法的特征是在它们的对映异构体和衍生物中选择性地选择几个目标胺或氨基酸对映异构体。该组合物的α值最好大于或等于4。这允许通过三个或更少的非色谱树脂床分离阶段分离这些对映异构体。
• [EN] CHIRAL DOPANT WITH PHENYLETHANEDIOL FUNCTIONALITY<br/>[FR] DOPANT CHIRAL PRESENTANT UNE FONCTIONNALITE PHENYLETHANEDIOL
  申请人：KONINKL PHILIPS ELECTRONICS NV

  公开号：WO2004002935A1

  公开（公告）日：2004-01-08

  The invention pertains to a phenylethanediol derivative having at least one polymerizable group, characterized in that the phenylethanediol derivative further comprises at least one photo-convertible group for adjusting the helical twisting power of the phenylethanediol derivative. According to a preferred embodiment the phenylethanediol has the formulawherein A stands for a bond or a p-phenylene group; B and B' are independently (O)p-CoH2o-O-CO-CR'=CH2, o being 2-12, p being 0 or 1, and R' being H or CH3; P stands for a CH2 or a C=O group; Q and Q' are independently selected from H, C1-C3 alkyl, C1-C3 alkoxy, halogen, and CN;n is an integer from 1 to 3; andm is an integer from 0 to 2; and:wherein A stands for a bond or a p-phenylene group; B is (O)p-CoH2o-O-CO-CR'=CH2, o being 2-12, p is 1, and R' being H or CH3; P stands for a CH2 or a C=O group; Q is selected from H, C1-C3 alkyl, C1-C3 alkoxy, halogen, and CN; andm is an integer from 0 to 2.

  本发明涉及一种具有至少一个可聚合基团的苯乙二醇衍生物，其特征在于该苯乙二醇衍生物进一步包含至少一个光可转换基团，用于调节苯乙二醇衍生物的螺旋扭转功率。根据首选实施例，苯乙二醇的式子为其中A代表键或p-苯撑基；B和B'独立地为（O）p-CoH2o-O-CO-CR'=CH2，其中o为2-12，p为0或1，R'为H或CH3；P代表CH2或C=O基团；Q和Q'独立地选自H、C1-C3烷基、C1-C3烷氧基、卤素和CN；n为1至3的整数；m为0至2的整数；和：其中A代表键或p-苯撑基；B为（O）p-CoH2o-O-CO-CR'=CH2，其中o为2-12，p为1，R'为H或CH3；P代表CH2或C=O基团；Q选自H、C1-C3烷基、C1-C3烷氧基、卤素和CN；m为0至2的整数。