(R)-(+)-1-(4-吡啶基)乙醇 | 27854-88-2

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (R)-(+)-1-(4-吡啶基)乙醇
• 中文别名: -4-羟乙基吡啶；(R)-(+)-α-甲基-4-吡啶甲醇；(R)-(+)-Alpha-甲基-4-吡啶甲醇
• 英文名称: (R)-1-(4-Pyridyl)ethanol
• 英文别名: (R)-1-(4-pyridinyl)ethanol；(R)-1-(pyridin-4-yl)ethan-1-ol；(R)-1-(pyridin-4-yl)ethanol；(1R)-1-pyridin-4-ylethanol
• CAS: 27854-88-2
• 化学式: C₇H₉NO
• mdl: MFCD00077865
• 分子量: 123.155
• InChiKey: HVOAMIOKNARIMR-ZCFIWIBFSA-N

物化性质

• 熔点：
  67-69 °C(lit.)
• 沸点：
  239.7±15.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933399090
• 储存条件：
  存放在2-8°C的阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-(4-吡啶基)乙醇 在 palladium on activated charcoal 正丁基锂 、 sodium azide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 2.08h， 生成 (S)-1-(4-吡啶基)乙胺
  参考文献：
  名称：

  3- and 4-Pyridylalkyl Adamantanecarboxylates:  Inhibitors of Human Cytochrome P450_17α (17α-Hydroxylase/C_17,20-Lyase). Potential Nonsteroidal Agents for the Treatment of Prostatic Cancer

  摘要：

  Various 3- and 4-pyridylalkyl 1-adamantanecarboxylates have been synthesized and tested for inhibitory activity toward the 17 alpha-hydroxylase and C-17,C-20-lyase activities of human testicular cytochrome P450(17 alpha). The 4-pyridylalkyl esters were much more inhibitory than their 3-pyridylalkyl counterparts. The most potent was (S)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate (3b; IC50 for lyase, 1.8 nM), whereas the (R)-enantiomer 3a was much less inhibitory (IC50 74 nM). Nearly as potent as 3b was the dimethylated counterpart, the 2-(4-pyridylpropan-2-yl) ester 5 (IC50 2.7 nM), which was also more resistant to degradation by esterases. In contrast to their 4-pyridyl analogs, the enantiomers of the 1-(3-pyridyl)ethyl ester were similarly inhibitory (IC50 for lyase; (R)-isomer 8a 150 nM, (S)-isomer 8b 230 nM). Amides corresponding to the 4-pyridylmethyl ester 1 and the (S)-1-(4-pyridyl)ethyl ester 3b, respectively 11 and 15b, were much less inhibitory than their ester counterparts. On the basis of a combination of inhibitory potency and resistance to esterases, the ester 5 was the best candidate for further development as a potential nonsteroidal inhibitor of cytochrome P450(17 alpha), for the treatment of prostate cancer.

  DOI：

  10.1021/jm950749y
• 作为产物：
  描述：

  (1R)-1-(3-吡啶基)乙酸乙酯 在 lipase Amano PS,potassium phosphate buffer 作用下， 反应 12.0h， 生成 (R)-(+)-1-(4-吡啶基)乙醇
  参考文献：
  名称：

  Reduction of β-Keto Esters with a Reductase: Construction of Plural Stereocenters Remote from the Reaction Center

  摘要：

  The reduction of sec-alkyl 2-methyl-3-oxobutyrate with a keto ester reductase from bakers' yeast (YKER-I) is accompanied by simultaneous dynamic and static resolution of chiral centers affording the corresponding (2R,3S,1'R)-hydroxy esters preferentially Thus, the enzyme discriminates three chiral centers simultaneously in high stereoselectivity producing useful chiral building blocks. To study the effect of the alcohol moiety which is located at a remote position from the reaction center, upon the interaction between the enzyme and a substrate, steady-state kinetic parameters, K-m and k(cat), of YKER-I for each (1'R)- and (1'S)-substrate have been determined. The results reveal that the stereochemistry at the alcohol moiety affects K-m rather than k(cat). (C) 1999 Academic Press.

  DOI：

  10.1006/bioo.1998.1106

文献信息

• Purification and Characterization of an NADH-Dependent Alcohol Dehydrogenase from<i>Candida maris</i>for the Synthesis of Optically Active 1-(Pyridyl)ethanol Derivatives
  作者：Shigeru KAWANO、Miho YANO、Junzo HASEGAWA、Yoshihiko YASOHARA

  DOI：10.1271/bbb.100528

  日期：2011.6.23

  A novel (R)-specific alcohol dehydrogenase (AFPDH) produced by Candida maris IFO10003 was purified to homogeneity by ammonium sulfate fractionation, DEAE-Toyopearl, and Phenyl-Toyopearl, and characterized. The relative molecular mass of the native enzyme was found to be 59,900 by gel filtration, and that of the subunit was estimated to be 28,900 on SDS-polyacrylamide gel electrophoresis. These results suggest that the enzyme is a homodimer. It required NADH as a cofactor and reduced various kinds of carbonyl compounds, including ketones and aldehydes. AFPDH reduced acetylpyridine derivatives, β-keto esters, and some ketone compounds with high enantioselectivity. This is the first report of an NADH-dependent, highly enantioselective (R)-specific alcohol dehydrogenase isolated from a yeast. AFPDH is a very useful enzyme for the preparation of various kinds of chiral alcohols.

  一种由Candida maris IFO10003产生的新型（R）-特异性醇脱氢酶（AFPDH）通过硫酸铵分级、DEAE-Toyopearl和Phenyl-Toyopearl纯化至均一，并进行了表征。通过凝胶过滤法测得该酶的原分子质量为59,900，而在SDS-聚丙烯酰胺凝胶电泳中亚基的估计分子质量为28,900。这些结果表明该酶为同源二聚体。它需要NADH作为辅因子，并能还原包括酮和醛在内的多种羰基化合物。AFPDH能高对映选择性地还原乙酰吡啶衍生物、β-酮酯和某些酮化合物。这是首例从酵母中分离出的依赖NADH的高对映选择性（R）-特异性醇脱氢酶的报道。AFPDH对于制备多种手性醇是非常有用的酶。
• Asymmetric synthesis of both enantiomers of secondary alcohols by reduction with a single microbe
  作者：Kaoru Nakamura、Keishi Takenaka、Mikio Fujii、Yoshiteru Ida

  DOI：10.1016/s0040-4039(02)00649-4

  日期：2002.5

  Both enantiomers of secondary alcohols were prepared by reduction of the corresponding ketones with a single microbe. Thus, reduction of aromatic ketones with Geotrichum candidum IFO 5767 afforded the corresponding (S)-alcohols in an excellent ee when amberlite™ XAD-7, a hydrophobic polymer, was added to the reaction system and the same microbe afforded (R)-alcohols also in an excellent ee when the

  通过用单个微生物还原相应的酮来制备仲醇的两种对映异构体。因此，还原芳族酮的白地霉IFO 5767，得到相应的（小号）时AMBERLITE™XAD-7，疏水性聚合物，加入到反应体系时，可以得到相同的微生物（ -醇在一个极好EE - [R ）-醇当在有氧条件下进行反应时，在优异的ee中也是如此。
• [EN] NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE THIÉNOPYRIMIDINE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2015097123A1

  公开（公告）日：2015-07-02

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

  式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如描述中所述。
• Highly enantioselective carbonyl reduction with borane catalyzed by chiral spiroborate esters derived from chiral beta-aminoalcohols
  申请人：Ortiz-Marciales Margarita

  公开号：US20080200672A1

  公开（公告）日：2008-08-21

  Novel spiroborate esters derived from non-recemic 1,2-amino alcohols were examined as chiral catalyst in the borane reduction of acetophenone and other aromatic ketones at room temperature. The optically active alcohols were obtained in excellent chemical yields and up to 99% ee with less than 10% catalyst.

  从非手性1,2-氨基醇衍生的新型螺环硼酸酯作为手性催化剂在室温下用于苯乙酮和其他芳香酮的硼氢化还原反应。光学活性醇以极高的化学产率获得，ee值高达99%，催化剂用量不到10%。
• Chiral Imidazo[1,5-<i>a</i>]pyridine–Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones
  作者：Chinna Ayya Swamy P、Andrii Varenikov、Graham de Ruiter

  DOI：10.1021/acs.organomet.9b00526

  日期：2020.1.27

  report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The

  本文中，我们报告了基于咪唑并[1,5- a]的一类多用途的N-杂环卡宾配体的合成和应用融合到手性恶唑啉助剂上的]吡啶-3-吡啶骨架。这些配体合成的关键步骤涉及通过氰基偶氮盐与各种2-氨基醇的微波辅助缩合来安​​装恶唑啉官能团。所得手性双齿NHC-恶唑啉配体与铑（I）形成稳定的络合物，铑是有效的催化剂，用于结构多样的酮的对映选择性氢化硅烷化。分离出相应的仲醇，收率好（通常> 90％），对映选择性好（极好）（80-93％ee）。报道的氢化硅烷化发生在环境温度（40°C）下，具有出色的官能团耐受性。甚至带有杂环取代基的酮（例如，