(R)-methoxy(1-naphthyl)acetic acid | 156942-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-methoxy(1-naphthyl)acetic acid
• 英文别名: (2R)-2-methoxy-2-naphthalen-1-ylacetic acid
• CAS: 156942-66-4
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: MIQWXVUTCSGZIZ-GFCCVEGCSA-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(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  冰片 、 (R)-methoxy(1-naphthyl)acetic 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 (R)-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 (R)-methoxy(1-naphthyl)acetic 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。
• Absolute configurational assignment of 3-hydroxycarotenoids
  作者：Thomas Andersson、Babak Borhan、Nina Berova、Koji Nakanishi、Jarle Andre Haugan、Synnøve Liaaen-Jensen

  DOI：10.1039/b002088p

  日期：——

  Attempts were made to develop an exciton chirality method applicable to the unique cases represented by 3-hydroxycarotenoids. However, this approach has so far not been successful. The 3-hydroxy configurations were therefore determined by the extended Mosher 1H-NMR method. Nine carotenoids with seven different end groups and of known 3-hydroxy configurations were derivatized with (R)- and (S)-methoxyphenylacetic acid (MPA); they all gave the expected shift differences. Three other auxiliary reagents with naphthalene and anthracene nuclei gave larger and consistent NMR shift differences, but they are not yet commercially available.

  人们试图开发一种适用于 3-羟基类胡萝卜素所代表的独特情况的激子手性方法。然而，这种方法至今尚未成功。因此，3-羟基构型是通过扩展的 Mosher 1H-NMR 方法确定的。用(R)-和(S)-甲氧基苯乙酸（MPA）对九种具有七个不同末端基团和已知 3- 羟基构型的类胡萝卜素进行了衍生化；它们都产生了预期的位移差异。另外三种具有萘核和蒽核的辅助试剂产生了更大且一致的核磁共振位移差异，但这些试剂尚未在市场上销售。
• Structures and Absolute Stereochemistry of Five New Secospatanes and a Spatane Isolated from the Brown Alga Dilophus okamurai Dawson.
  作者：Hiroshi YAMASE、Kimie UMEMOTO、Takashi OOI、Takenori KUSUMI

  DOI：10.1248/cpb.47.813

  日期：——

  Five new secospatane diterpenoids, secospatacetal A, B, C, D, and E have been isolated from the brown alga Dilophus okamurai DAWSON, and their structures as well as absolute configurations have been elucidated by means of NMR spectroscopy and chemical transformations Also, the structure of a known spatane diterpene has been revised.

  从褐藻 Dilophus okamurai DAWSON 中分离得到 5 种新的 secospatane 二萜化合物 secospatacetal A、B、C、D 和 E，并通过核磁共振波谱和化学转化阐明了它们的结构和绝对构型。已知的spatane二萜的结构已被修改。
• 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.