(S)-1-(2-pyridyl)propanol | 18209-34-2

• 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
• 英文名称: (S)-1-(2-pyridyl)propanol
• 英文别名: (S)-2-(1-hydroxypropyl)pyridine；1-(2'-pyridyl)-1-propanol；(S)-1-(2-pyridyl)-1-propanol；(S)-1-(pyridine-2-yl)propan-1-ol；(S)-1-(pyridin-2-yl)propan-1-ol；1-(pyridin-2-yl)propan-1-ol；(S)-1-pyridin-2-ylethanol；(1S)-1-(pyridin-2-yl)propan-1-ol；(1S)-1-pyridin-2-ylpropan-1-ol
• CAS: 18209-34-2
• 化学式: C₈H₁₁NO
• mdl: MFCD18427800
• 分子量: 137.181
• InChiKey: OBUPVPZCSVEBQN-QMMMGPOBSA-N

物化性质

• 沸点：
  214.5±0.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氰基吡啶 在 C₆₀H₆₀P₂Rh⁽¹⁺⁾*BF₄^(1-) 、 氢气 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0 ℃ 、810.65 kPa 条件下， 反应 24.0h， 生成 (S)-1-(2-pyridyl)propanol
  参考文献：
  名称：

  Rhodium Catalyzed Asymmetric Hydrogenation of 2-Pyridine Ketones

  摘要：

  Catalyzed by [Rh(COD)Binapine]BF4, the asymmetric hydrogenation of 2-pyridine ketones has been achieved with excellent enantioselectivities (enantiomeric excesses up to 99%) under mild conditions. This method is suitable for various kinds of 2-pyridine ketones and their derivatives. A number of enantiomerically pure chiral 2-pyridine-aryl/alkyl alcohols were prepared through hydrogenation, which can be used directly in organic synthesis.

  DOI：

  10.1021/acs.orglett.5b01878

文献信息

• Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
  作者：Ömer Dilek、Mustafa A. Tezeren、Tahir Tilki、Erkan Ertürk

  DOI：10.1016/j.tet.2017.11.054

  日期：2018.1

  Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the

  高效和模块化的手性2-（2-羟基芳基）醇（HAROLs）的合成，带有一个酚和一个醇羟基的新型1,4-二醇已被开发出来，这导致在对映异构体中生成结构多样的HAROLS小文库纯形式。在考察的不同HAROL中，基于茚满骨架的HAROL在Ti（O i Pr）4（y高达97％， 88％ee）并在三田膦的促进下在Morita-Baylis-Hillman反应中作为氢键供体有机催化剂发挥作用。
• Synthesis of New Chiral Aliphatic Amino Diselenides and Their Application as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Antonio L. Braga、Marcio W. Paixão、Diogo S. Lüdtke、Claudio C. Silveira、Oscar E. D. Rodrigues

  DOI：10.1021/ol034773e

  日期：2003.7.1

  [reaction: see text] A set of chiral aliphatic amino diselenides have been synthesized from readily available starting materials in a straightforward synthetic route via the ring-opening reaction of the parent aziridines. These ligands have been tested as catalysts for the enantioselective addition of diethylzinc to aldehydes. The influence of the alkyl group substituents on the stereoselectivity has

  [反应：见正文]通过母体氮丙啶的开环反应，以简单的合成路线由容易获得的起始原料合成了一组手性脂肪族氨基二硒化物。这些配体已经作为二乙基锌对醛的对映选择性加成的催化剂进行了测试。已经研究了烷基取代基对立体选择性的影响，并且在最佳情况下，通过仅使用0.5mol％的手性二硒化物3a可以得到高达99％的对映体过量。
• A Catalytic and Mechanistic Investigation of Optically Active Helical Poly[3-(9-alkylfluoren-9-yl)propylene oxide]s in the Enantioselective Addition of Ethylmagnesium Bromide to Aldehydes
  作者：Anlin Zhang、Nianfa Yang、Liwen Yang、Dan Peng

  DOI：10.1246/cl.131101

  日期：2014.4.5

  Optically active helical poly[(S)-3-(9-alkylfluoren-9-yl)propylene oxide]s (poly-(S)-AFPOs) without additional stereogenic units were used to induce the enantioselective addition of ethylmagnesium bromide to aldehydes, giving up to 53% ee of the products. It is the helically chiral environment rather than the point chirality that governs the enantioselective inducement of the addition reaction. Poly-(S)-AFPOs could be recovered simply, post-treated conveniently and used repeatedly.

  光学活性的螺旋聚[(S)-3-(9-烷基芴-9-基)丙烯氧化物]（聚-(S)-AFPOs）在没有额外立体中心的情况下用于诱导乙基溴化镁对醛的选择性加成，产物的对映体过量可达53%。在该加成反应的选择性诱导中，主导因素是螺旋手性环境而非点手性。聚-(S)-AFPOs可以简单回收，方便后处理并可重复使用。
• Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes
  作者：Semistan Karabuga、Murat Cakici、Cavit Kazaz、Ertan Sahin、Hamdullah Kilic、Sabri Ulukanli

  DOI：10.1039/c1ob06205k

  日期：——

  A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.

  一系列亚砜通过铅四醋酸盐的氧化加成反应与3-氨基喹唑啉酮进行硫氧化胺化。在六甲基二硅氮的存在下，它们首次应用于对芳香醛的催化对映选择性加成，在2-甲氧基苯甲醛的情况下，产物的对映体纯度（ee）达到92%。
• α-Pinene-Based New Chiral Ionic Liquids and their Application as Phase Transfer Catalysts in Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Sanjay Malhotra、Yun Wang、Vineet Kumar

  DOI：10.2174/157017809787893073

  日期：2009.4.1

  Amino alcohol functionalized new chiral ionic liquids have been synthesized from (+)-α-pinene, an easily available natural product. The effectiveness of these CILs as phase transfer catalysts (PTC) in enantioselective C-C bond formation has been demonstrated through the addition of diethylzinc to representative aldehydes, and the corresponding chiral alcohols with good yields and enantiomeric excess

  由（+）-α-pine烯（一种容易获得的天然产物）合成了氨基醇官能化的新型手性离子液体。这些CIL作为对映选择性CC键形成相转移催化剂（PTC）的有效性已通过将二乙基锌添加到代表性的醛中得到证明，并且获得了具有良好收率和对映体过量的相应手性醇。