(S)-1-胡椒基-2-丙醇 | 521097-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: (S)-1-胡椒基-2-丙醇
• 中文别名: (R)-1-(3,4-亚甲二氧基苯基)-2-丙醇
• 英文名称: (-)-1-benzo[1,3]dioxol-5-yl-2-propanol
• 英文别名: (R)-1-piperonyl-2-propanol；(R)-1-[3,4-(methylenedioxy)phenyl]propan-2-ol；(2R)-1-(1,3-benzodioxol-5-yl)propan-2-ol；(R)-1-(benzo[d][1,3]dioxol-5-yl)propan-2-ol；(2R)-1-(2H-1,3-benzodioxol-5-yl)propan-2-ol
• CAS: 521097-97-2
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD11111319
• 分子量: 180.203
• InChiKey: RVMKZYKJYMJYDG-SSDOTTSWSA-N

物化性质

• 沸点：
  292.1±9.0℃ (760 Torr)
• 密度：
  1.219±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  130.5±18.7℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (S)-1-胡椒基-2-丙醇 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (2S)-1-(1,3-苯并二氧戊环-5-基)-2-丙醇
  参考文献：
  名称：

  Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol: an efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (−)-talampanel

  摘要：

  (S)-(+)-alpha-Methyl-1,3-benzodioxole-5-ethanoI 5 is a chiral building block in the synthesis of the future drug (-)-talam-panel 1. Amano PS-induced enantioselective acylation of (+/-)-3 at 50degreesC using vinyl acetate as acyl donor furnished (+)-5 in 53% yield and 80% e.e., and the corresponding acetyl derivative (-)-(R)-alpha-methyl-1,3-benzodioxole-5-ethyl acetate 6 in 44% yield and 96% e.e. The base-catalysed methanolysis of (-)-6 followed by Mitsunobu inversion and subsequent methanolysis of the product, (+)-8 also gave the desired (+)-5 in 38% overall yield (four steps) and 96% e.e. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00836-4
• 作为产物：
  描述：

  [(2R)-1-(1,3-benzodioxol-5-yl)propan-2-yl] acetate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 生成 (S)-1-胡椒基-2-丙醇
  参考文献：
  名称：

  Kinetic and chemical resolution of different 1-phenyl-2-propanol derivatives

  摘要：

  Seven chiral target molecules containing a hydroxy group have been resolved by both biocatalytic and chemical means. The lipase-catalyzed acylation mainly yielded the acylated derivative of the (R)-alcohols with moderate enantiomeric excess and the enantiopure (S)-alcohols. In the course of the chemical resolution, first the dicarboxylic acid monoesters of the target molecules were synthesized and the resolution of these monoesters was attempted by different homochiral bases. By re-resolution and/or optimization of the reaction time and/or recrystallization, respectively, each molecule was produced in very high enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.019

文献信息

• Chemoenzymatic Synthesis of Enantiomerically Pure<i>syn</i>-Configured 1-Aryl-3-methylisochroman Derivatives
  作者：Robert C. Simon、Eduardo Busto、Nina Richter、Ferdinand Belaj、Wolfgang Kroutil

  DOI：10.1002/ejoc.201301429

  日期：2014.1

  A two-step synthesis of various enantiomerically pure 1-aryl3-methylisochroman derivatives was accomplished through asymmetric biocatalytic ketone reduction followed by an oxa-Pictet–Spengler reaction. The compounds were obtained in good to excellent yield (47–92%) in favor of the syn diastereomers [dr (syn/anti) up to 99:1]. Enantiopure arylpro

  通过不对称生物催化酮还原和氧杂-皮克泰-斯宾格勒反应，完成了各种对映体纯 1-芳基 3-甲基异色满衍生物的两步合成。这些化合物以良好到极好的收率 (47–92%) 获得，有利于顺式非对映异构体 [dr (syn/anti) 高达 99:1]。对映体纯芳基脯氨酸
• OPTICAL ISOMERS OF DIHYDRO-2,3-BENZODIAZEPINES AND THEIR STEREOSELECTIVE SYNTHESIS
  申请人：Ling Istvan

  公开号：US20090233913A1

  公开（公告）日：2009-09-17

  The present invention relates to dihydro-2,3-benzodiazepine compounds of high enantiomeric purity according to the general formula (I), which contain an asymmetric centre at the position 4 of the dihydro-2,3-benzodiazepine compound, and the preparation thereof and the used intermediates as well. These compounds have anti-convulsiveA muscle relaxant and neuroprotective effect due their non-competitive AMPA antagonistic properties.

  本发明涉及高对映纯度的二氢-2,3-苯并二氮平化合物，其通式为(I)，其中在二氢-2,3-苯并二氮平化合物的4位含有不对称中心，以及其制备方法和用作中间体。这些化合物具有抗惊厥、肌肉松弛和神经保护作用，因为它们具有非竞争性AMPA拮抗作用。
• From Diazonium Salts to Optically Active 1‐Arylpropan‐2‐ols Through a Sequential Photobiocatalytic Approach
  作者：Laura Rodríguez‐Fernández、Jesús Albarrán‐Velo、Iván Lavandera、Vicente Gotor‐Fernández

  DOI：10.1002/adsc.202300245

  日期：2023.6.13

  The photocatalytic Meerwein arylation between aromatic diazonium salts and isopropenyl acetate under blue LED light irradiation in aqueous medium has been deeply investigated. Optimization of the reaction conditions in terms of substrate concentration, ester equivalents, cosolvent type and amount, reaction time and photocatalyst source, has allowed the access to a variety of 1-arylpropan-2-ones with

  已经深入研究了在水性介质中蓝色 LED 光照射下芳香重氮盐和乙酸异丙烯酯之间的光催化 Meerwein 芳基化。在底物浓度、酯当量、共溶剂类型和用量、反应时间和光催化剂来源方面优化反应条件，允许使用 9-mesityl 获得各种 1-arylpropan-2-ones，产率高达 95% -10-甲基吖啶高氯酸盐 ([Acr-Mes]ClO 4). 接下来，通过将 Meerwein 芳基化与相应酮中间体的生物还原相结合，完成了单锅顺序光生物催化线性方法的设计。因此，根据醇脱氢酶的立体偏好，总共获得了 19 对 1-arylpropan-2-ol 对映异构体。全球收率高达 76%，立体选择性高至极佳（90 至 >99% ee）。此外，通过一锅三步顺序光生物催化方案，可以从苯胺开始获得两种 1-苯基丙-2-醇对映体（51-53% 产率）。
• Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH)
  作者：Kousuke Inoue、Yoshihide Makino、Nobuya Itoh

  DOI：10.1016/j.tetasy.2005.06.036

  日期：2005.8

  Alcohol dehydrogenase (LSADH) isolated from Leifsonia sp. S749 was used to produce (R)-chiral alcohols. The enzyme with a broad substrate range reduced various prochiral ketones and keto esters to yield optically active secondary alcohols with a high enantiomeric excess. LSADH transferred the pro-S hydrogen of NADH to the carbonyl moiety of phenyl trifluoromethyl ketone 13 through its re face to give (S)-1-pheilyl-2,2,2-trifluoroethatiol 40. LSADH was able to efficiently reproduce NADH when 2-propanol was used as a hydrogen donor in the reaction mixture. (c) 2005 Elsevier Ltd. All rights reserved.
• [EN] OPTICAL ISOMERS OF DIHYDRO-2,3-BENZODIAZEPINES AND THEIR STEREOSELECTIVE SYNTHESIS<br/>[FR] ISOMERES OPTIQUES DE DIHYDRO-2,3-BENZODIAZEPINES ET LEUR SYNTHESE STEREOSELECTIVE
  申请人：EGIS GYOGYSZERGYAR NYRT

  公开号：WO2007077469A1

  公开（公告）日：2007-07-12

  [EN] The present invention relates to dihydro-2,3-benzodiazepine compounds of high enantiomeric purity according to the general formula (I), which contain an asymmetric centre at the position 4 of the dihydro-2,3-benzodiazepine compound, and the preparation thereof and the used intermediates as well. These compounds have anti-convulsiveA muscle relaxant and neuroprotective effect due their non-competitive AMPA antagonistic properties.
  [FR] La présente invention concerne des composés de dihydro-2,3-benzodiazépine de pureté énantiomérique élevée selon la formule générale (I), qui contiennent un centre asymétrique à la position 4 du composé de dihydro-2,3-benzodiazépine, et leur préparation ainsi que les intermédiaires utilisés. Ces composés ont un effet myorelaxant anticonvulsif neuroprotecteur en raison de leurs propriétés antagonistes d'AMPA non compétitives.