(S)-α-methoxynaphthalen-1-ylacetic acid | 160727-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-α-methoxynaphthalen-1-ylacetic acid
• 英文别名: (S)-methoxy-(1-naphthyl)acetic acid；(S)-1-NMA；(S)-alpha-Methoxy-2-naphthylacetic acid；(2S)-2-methoxy-2-naphthalen-1-ylacetic acid
• CAS: 160727-80-0
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: MIQWXVUTCSGZIZ-LBPRGKRZSA-N

物化性质

• 熔点：
  113.2-114.4 °C
• 沸点：
  396.2±22.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  冰片 、 (S)-α-methoxynaphthalen-1-ylacetic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 (-)-bornyl (S)-α-methoxy-α-(1-naphthyl)acetate
  参考文献：
  名称：

  Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions

  摘要：

  The factors governing the efficiency of arylmethoxyacetic acids (AMAAs) For the determination of the absolute configuration of alcohols by NMR, have been identified and their influence studied. The largest Delta delta(RS) values are obtained either increasing the size of the aryl ring (i.e. alpha-(9-anthryl)-alpha-methoxyacetic acid, 5), or the population of the most stable conformer (i.e. reagent 3 at low temperature). The use of 5 to induce useful shifts on remote protons of complex molecules (i.e. androsterone) is described.

  DOI：

  10.1016/s0040-4020(97)00512-7
• 作为产物：
  描述：

  2-甲氧基-2-萘-1-基乙酸 生成 (S)-α-methoxynaphthalen-1-ylacetic acid
  参考文献：
  名称：

  （R）-和（S）-α-甲氧基-（1-萘基）乙酸：通过分步结晶进行拆分，并用于烷基亚砜的NMR立体化学分析

  摘要：

  α-甲氧基-（1-萘基）乙酸（1-NMA）的两种对映体都可以通过使用1-（1-萘基）乙胺的对映体进行分步结晶而方便地获得。1-NMA被证明对区分准对称脂肪族亚砜的对映体信号非常有效。

  DOI：

  10.1016/s0957-4166(98)00077-9

文献信息

• 13C NMR as a general tool for the assignment of absolute configuration
  作者：Iria Louzao、José Manuel Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1039/c0cc02774j

  日期：——

  (13)C NMR, alone or in combination with (1)H NMR, allows the assignment of the absolute configuration of chiral alcohols, amines, carboxylic acids, thiols, cyanohydrins, sec,sec-diols and sec,sec-aminoalcohols, derivatized with appropriate chiral auxiliaries. This extends the assignment possibilities of NMR to fully deuterated and to nonproton containing compounds.

  （13）C NMR单独或与（1）H NMR结合使用，可以确定衍生化的手性醇，胺，羧酸，硫醇，氰醇，仲，仲二醇和仲，仲氨基醇的绝对构型与适当的手性助剂。这将NMR的赋值可能性扩展到了完全氘代和不含质子的化合物。
• Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton-Part 2
  作者：Ko Yasumoto、Akinori Nishigami、Hiroaki Aoi、Chise Tsuchihashi、Fumie Kasai、Takenori Kusumi、Takashi Ooi

  DOI：10.1248/cpb.56.129

  日期：——

  4,8-Dimethylnonyl sulfate (1) and 3-methyl-4E-decenyl sulfate (2) were isolated from Daphnia pulex as the Daphnia kairomones that induced morphological defense of a freshwater phytoplankton Scenedesmus gutwinskii var. heterospina (NIES-802). The absolute configuration at C4 of 1 was determined by Ohrui's method applied to alcohol 3. The absolute stereochemistry at C3 of 2 was determined by 1H-NMR analysis of the (R)-1NMA ester of alcohol 11.

  4,8-二甲基壬基硫酸酯（1）和3-甲基-4E-癸烯基硫酸酯（2）是从水蚤Daphnia pulex中分离得到的两种信息素，能够诱导淡水浮游植物Scenedesmus gutwinskii var. heterospina（NIES-802）产生形态防御反应。根据Ohrui的方法对醇3的应用，确定了化合物1在C4位的绝对构型。通过分析醇11的（R）-1NMA酯的1H-NMR，确定了化合物2在C3位的绝对立体化学。
• Isolation and Absolute Configuration Determination of Aliphatic Sulfates as the Daphnia Kairomones Inducing Morphological Defense of a Phytoplankton
  作者：Ko Yasumoto、Akinori Nishigami、Fumie Kasai、Takenori Kusumi、Takashi Ooi

  DOI：10.1248/cpb.54.271

  日期：——

  2,6-Dimethylheptyl sulfate (1) and 6-methyloctyl sulfate (3) were isolated from Daphnia pulex as the Daphnia kairomones that induced morphological defense of a freshwater phytoplankton Scenedesmus gutwinskii var. heterospina (NIES-802). The absolute stereochemistry at C2 of 1 was determined by 1H-NMR analysis of the (R)-MTPA ester of alcohol 2. The absolute configuration at C6 of 3 was determined by Ohrui's method applied to alcohol 4.

  从水溞中分离出 2,6-二甲基庚基硫酸盐 (1) 和 6-甲基辛基硫酸盐 (3)，作为水蚤利他素诱导淡水浮游植物 Scenedesmus gutwinskii var. 的形态防御。异脊柱（NIES-802）。通过对醇 2 的 (R)-MTPA 酯进行 1 H-NMR 分析来确定 1 的 C2 处的绝对立体化学。通过应用于醇 4 的 Ohrui 方法来确定 3 的 C6 处的绝对构型。
• Enantioselective synthesis of arylmethoxyacetic acid derivatives
  作者：F.Javier Moreno-Dorado、Francisco M. Guerra、Marı́a J. Ortega、Eva Zubı́a、Guillermo M. Massanet

  DOI：10.1016/s0957-4166(03)00023-5

  日期：2003.2

  The preparation of several arylmethoxyacetic acids by a sequence of asymmetric dihydroxylation and further oxidation of the resulting glycol with TEMPO/NaClO/NaClO2 is described. The scope and limitations of the reaction are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Conformational Structure and Dynamics of Arylmethoxyacetates: DNMR Spectroscopy and Aromatic Shielding Effect
  作者：Sh. K. Latypov、J. M. Seco、E. Quinoa、R. Riguera

  DOI：10.1021/jo00108a008

  日期：1995.2

  The ground state conformational geometry and energy of esters of (R)- and (S)-arylmethoxyacetic acids were evaluated from low temperature H-1 and C-13 NMR spectra and by means of MM, AM1, and aromatic shielding effect calculations. In solution, the title compounds are constituted by two rotamers in equilibrium. Rotamer ap has the C-alpha-O and C=O bonds antiperiplanar and rotamer sp (lower in energy by 0.4-1.1 kcal/mol) has these bonds synperiplanar. In both the ap and the sp the aryl ring is ca. perpendicular to the C=O bond and coplanar with the CalphaH bond. Their relative populations and its temperature dependence evaluated by DNMR spectra are in agreement with the stereoselectivity reported for Diels-Alder reactions of dienyl-AMAA esters and support the ''perpendicular model'' proposed to account for that stereoselectivity. For conformations in which the aryl ring shields the alcohol moiety of the ester, calculated ring current shielding increments compare well with experimental shift values obtained from low-temperature NMR spectra and agree with the conformational model used in the Mislow-Dale-Mosher-Trost method for chiral recognition by NMR.