(R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester | 133867-57-9

• 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: (R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester
• 英文别名: methyl (2R)-2-(oxan-2-yloxy)-2-phenylacetate
• CAS: 133867-57-9
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: OIODXZPBINGTGA-ZGTCLIOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester 在 lithium aluminium tetrahydride 、 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 氢气 作用下， 生成 (R)-Phenyl-[(tetrahydro-pyran-2-yloxy)]-acetic acid methyl ester
  参考文献：
  名称：

  配位球中的不对称自由基反应。四、钌 (II) 催化磺酰氯与 1-苯基丙烯的不对称加成

  摘要：

  在 Ru2Cl4[(-)-diop]3 催化下，甲烷和对甲苯磺酰氯与 1-苯基丙烯的不对称加成得到光学活性 1:1 的加合物，(+)-(1R,2RS)-1-chloro-2-甲基磺酰基-1-苯基丙烷 (2) 和 (+)-(1R,2RS)-1-chloro-1-phenyl-2-tosylpropane (3)，约 13–19%ee。类似地，当使用 Ru2Cl4[(+)-diop]3 时，得到 (-)-(1S,2RS)-2 和 (-)-(1S,2RS)-3。对映体分化被认为发生在从钌 (III) 物种到配位球中的碳自由基的氯原子转移步骤中。

  DOI：

  10.1246/bcsj.62.648

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。
• trans-1,3-Dithiane-1,3-dioxide, a new chiral acyl anion equivalent for the preparation of masked activated acids: application to the synthesis of α-hydroxy acid derivatives
  作者：Varinder K. Aggarwal、Abraham Thomas、Richard J. Franklin

  DOI：10.1039/c39940001653

  日期：——

  trans-1,3-Dithiane-1,3-dioxide reacts with high diastereoselectivity with aromatic aldehydes and the 1,3-dithiane-1,3-dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily transformed into acids, esters, amides, ketones and aldehydes.

  反式-1，3-二噻吩-1，3-二氧化物与芳族醛具有高的非对映选择性，并且通过进行Pummerer反应可以容易地将1，3-二噻吩-1，3-二氧化物部分转化为巯基酯，而没有外消旋化。硫醇酯是可以容易地转化成酸，酯，酰胺，酮和醛的基团。
• Recognition by new symmetrically substituted chiral diphenyl- and di-tert-butylpyridino-18-crown-6 and asymmetrically substituted chiral dimethylpyridino-18-crown-6 ligands of the enantiomers of various organic ammonium perchlorates
  作者：Peter Huszthy、Jerald S. Bradshaw、Cheng Y. Zhu、Reed M. Izatt、Shneior Lifson

  DOI：10.1021/jo00010a028

  日期：1991.5

  Three new chiral pyridino-18-crown-6 ligands have been prepared. These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms. The chiral di-tert-butyl-substituted diester crown analogue was also prepared. The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt. A high degree of chiral recognition in CD2Cl2 of the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of activation (DELTA-G(c) double-ended-dagger) values determined by temperature-dependent H-1 NMR spectroscopy. The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct H-1 NMR technique.
• 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
  作者：Masayuki Kameyama、Nobumasa Kamigata、Michio Kobayashi

  DOI：10.1021/jo00391a025

  日期：1987.7
• Enantioselective protonation of samarium enolates by a C2-symmetric chiral diol
  作者：Seiji Takeuchi、Akiko Ohira、Norikazu Miyoshi、Hajime Mashio、Yoshiaki Ohgo

  DOI：10.1016/0957-4166(94)80086-3

  日期：1994.9

  High enantioselectivity (up to 97%ee) have been achieved in the protonation of samarium enolates which were generated by SmI2-mediated cross-coupling reaction between unsymmtrical dialkylketene and allyl iodide, using a C-2-symmetric chiral diol as a proton source. The stereochemistry of enolate formation and of the enantioselective protonation is discussed.