(1R)-endo-(+)-fenchylalcohol | 64439-31-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-endo-(+)-fenchylalcohol
• 英文别名: (+)-β-fenchyl alcohol；(+)-β-fenchol；(1R)-1,3,3-trimethyl-norbornan-2exo-ol；(1R:2S)-1.3.3-Trimethyl-norbornanol-(2)；(+/-)-1,3,3-Trimethyl-norbornan-2exo-ol；(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 64439-31-2
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: IAIHUHQCLTYTSF-QXFUBDJGSA-N

物化性质

• 物理描述：
  White to pale yellow crystals; Camphoraceous aroma
• 熔点：
  45.75 °C
• 溶解度：
  Soluble in vegetable oils; Very slightly soluble in water

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-endo-(+)-fenchylalcohol 在 aluminum oxide 、 palladium on activated charcoal 盐酸 、 氨 、 氢气 、 氯化铵 、 三氯氧磷 作用下， 以 甲醇 、 正庚烷 、 水 为溶剂， 25.0~200.0 ℃ 、196.12 kPa 条件下， 反应 23.0h， 生成 (7,7-dimethylnorborn-2R-yl)-(R,S)-alanine hydrochloride
  参考文献：
  名称：

  新型高强度人工甜味剂（S）-天冬氨酰-（7,7-二甲基降冰片-2R-基）-（S）-丙氨酸甲酯的合成方法的改进

  摘要：

  （S）-天冬氨酰-（7,7-二薄荷基降冰片烯-2R-基）-（S）-丙氨酸甲酯（1）由（+）-α-苯甲醇（3）作为手性合成子以九步合成。表现甜度所需的控制1的侧链立体化学的关键步骤是烯烃4的催化加氢甲酰化和使用酰基转移酶I的外消旋氨基酸9的酶促拆分。

  DOI：

  10.1016/s0040-4020(01)88486-6
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 lithium aluminium tetrahydride 作用下， 以 甲基叔丁基醚 为溶剂， 生成 (1R)-endo-(+)-fenchylalcohol
  参考文献：
  名称：

  新型环状醇三氧化氢热分解的合成及动力学规律

  摘要：

  通过一系列环醇的低温 (-78 °C) 臭氧分解合成环状三氧化二氢，并使用 1 H NMR 光谱进行鉴定。研究了合成的三氧化二氢的热分解动力学规律。以三氧化氢环己醇为例，首次得到了三氧化氢醇诱导分解的实验证明。显示了环状取代基对三氧化氢的热稳定性的影响。

  DOI：

  10.1007/s11172-016-1322-2

文献信息

• Method to separate stereoisomers
  申请人：Krsek R. George

  公开号：US20050171155A1

  公开（公告）日：2005-08-04

  A method to resolve the stereoisomers of an optically active compound comprising an amine moiety. The method provides a mixture comprising two stereoisomers of a compound comprising a amine moiety. The method supplies l-fenchyloxyacetic acid, treats the mixture of stereoisomers with that l-fenchyloxyacetic acid, and collects one of those two stereoisomers having greater than a 99 percent enantiomeric excess.

  一种用于解决含有胺基团的光学活性化合物的立体异构体的方法。该方法提供了一个包含一种胺基团的化合物的两个立体异构体的混合物。该方法供应l-芬基氧乙酸，用该l-芬基氧乙酸处理立体异构体的混合物，并收集其中一个具有大于99%对映体过量的立体异构体。
• Organic reactions in a solid matrix-VII sodium on alumina : A convenient reagent for reduction of ketones, esters and oximes
  作者：Satendra Singh、Sukh Dev

  DOI：10.1016/s0040-4020(01)80249-0

  日期：1993.1

  Sodium dispersed on alumina is described and evaluated as a convenient off-the-shelf reagent (in a wax-coated form) for reduction of ketones, esters and oximes. While isopropanol is the preferred proton donor for the reduction of ketones and oximes, t-butanol is the alcohol of choice for the reduction of esters.

  描述并分散在氧化铝上的钠是一种方便的现成试剂（蜡包衣形式），用于还原酮，酯和肟。异丙醇是用于还原酮和肟的优选质子供体，而叔丁醇是用于还原酯的选择的醇。
• Selective ruthenium-catalyzed epimerization of chiral sec-alcohols
  作者：Otto Långvik、Denys Mavrynsky、Reko Leino

  DOI：10.1016/j.cattod.2014.05.006

  日期：2015.3

  Extension of secondary alcohol racemization catalyzed by homogeneous half-sandwich ruthenium complexes to the epimerization of natural products containing additional non-functionalized stereo-centers has been investigated. Ruthenium-catalysed epimerization of the sec-alcohols (-)-menthol, (-)-isopulegol, (+)-borneol, (+)-fenchol and cholesterol under mild reaction conditions and low catalyst loadings (2 mol%) provides rapid access to their less abundant diastereoisomers (+)-neomenthol, (+)-neoisopulegol, isoborneol, beta-fenchol and epicholesterol in admixture with the parent diastereomers in ratios ranging from 1:4.9 to 1:2.4 (epimer: parent). (C) 2014 Elsevier B.V. All rights reserved.
• Substrate flexibility and reaction specificity of tropinone reductase-like short-chain dehydrogenases
  作者：Nicole Reinhardt、Juliane Fischer、Ralph Coppi、Elke Blum、Wolfgang Brandt、Birgit Dräger

  DOI：10.1016/j.bioorg.2014.01.004

  日期：2014.4

  Annotations of protein or gene sequences from large scale sequencing projects are based on protein size, characteristic binding motifs, and conserved catalytic amino acids, but biochemical functions are often uncertain. In the large family of short-chain dehydrogenases/reductases (SDRs), functional predictions often fail. Putative tropinone reductases, named tropinone reductase-like (TRL), are SDRs annotated in many genomes of organisms that do not contain tropane alkaloids. SDRs in vitro often accept several substrates complicating functional assignments. Cochlearia officinalis, a Brassicaceae, contains tropane alkaloids, in contrast to the closely related Arabidopsis thaliana. TRLs from Arabidopsis and the tropinone reductase isolated from Cochlearia (CoTR) were investigated for their catalytic capacity. In contrast to CoTR, none of the Arabidopsis TRLs reduced tropinone in vitro. NAD(H) and NADP(H) preferences were relaxed in two TRLs, and protein homology models revealed flexibility of amino acid residues in the active site allowing binding of both cofactors. TRLs reduced various carbonyl compounds, among them terpene ketones. The reduction was stereospecific for most of TRLs investigated, and the corresponding terpene alcohol oxidation was stereoselective. Carbonyl compounds that were identified to serve as substrates were applied for modeling pharmacophores of each TRL. A database of commercially available compounds was screened using the pharmacophores. Compounds identified as potential substrates were confirmed by turnover in vitro. Thus pharmacophores may contribute to better predictability of biochemical functions of SDR enzymes. (C) 2014 Elsevier Inc. All rights reserved.
• Synthesis and Sweetness Characteristics of <scp>l</scp>-Aspartyl-<scp>d</scp>-Alanine Fenchyl Esters
  作者：Yoshifumi Yuasa、Akira Nagakura、Haruki Tsuruta

  DOI：10.1021/jf010344o

  日期：2001.10.1

  Four isomers of the L-aspartyl-D-alanine fenchyl esters were prepared as potential peptide sweeteners. L-Aspartyl-D-alanine (+)-alpha -fenchyl ester and L-aspartyl-D-alanine (-)-beta -fenchyl ester showed sweetness with potencies 250 and 160 times higher than that of sucrose, respectively. In contrast, L-aspartyl-D-alanine (+)-beta -fenchyl ester and L-:aspartyl-D-alanine (-)-alpha -fenchyl ester had the highest sweetness potencies at 5700 and 1100 times that of sucrose, respectively. In particular, L-aspartyl-D-alanine (-)-alpha -fenchyl ester had an excellent sweetness quality; but L-,aspartyl-D-alanine (+)-beta -fenchyl ester did not have an excellent quality of sweetness because it displayed an aftertaste caused by the strong sweetness.