(1S)-1-(3-吡啶基)-3-丁烯-1-醇 | 144635-03-0

• 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: (1S)-1-(3-吡啶基)-3-丁烯-1-醇
• 英文名称: (S)-1-(3-pyridyl)-3-buten-1-ol
• 英文别名: (S)-1-(3-pyridyl)but-3-en-1-ol；(S)-1-(pyridin-3-yl)but-3-en-1-ol；(S)-1-(3-Pyridinyl)-3-butene-1-ol；(1S)-1-pyridin-3-ylbut-3-en-1-ol
• CAS: 144635-03-0
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: NRXCONFJQGCIBF-VIFPVBQESA-N

物化性质

• 沸点：
  276.2±25.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S)-1-(3-吡啶基)-3-丁烯-1-醇 在 lithium aluminium tetrahydride 、 sodium azide 、 bis(cyclohexanyl)borane 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 D-(+)-尼古丁
  参考文献：
  名称：

  A short and efficient synthesis of unnatural (R)-nicotine

  摘要：

  A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01675-0
• 作为产物：
  描述：

  1-(pyridin-3-yl)but-3-en-1-ol 在 (+)-β-chlorodiisopinocampheylborane 、 邻苯二甲酸二甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (1S)-1-(3-吡啶基)-3-丁烯-1-醇
  参考文献：
  名称：

  对映选择性还原杂芳族β，γ-不饱和酮，作为醛的烯丙基硼化的替代方法。：应用：SIB-1508Y的不对称合成

  摘要：

  发现杂芳族β，γ-不饱和酮的对映选择性还原是相应醛的烯丙基硼化的有效和方便的替代方法。该新方法用于SIB-1508Y 2的形式不对称合成。

  DOI：

  10.1016/s0040-4020(02)00819-0

文献信息

• Efficient Enantiomeric Synthesis of Pyrrolidine and Piperidine Alkaloids from Tobacco
  作者：Felpin、Sandrine Girard、Giang Vo-Thanh、Richard J. Robins、Jean Villiéras、Jacques Lebreton

  DOI：10.1021/jo010386b

  日期：2001.9.1

  An enantiomeric synthesis of six piperidine and pyrrolidine alkaloids, (S)-nornicotine 1, (S)-nicotine 2, (S)-anatabine 3, (S)-N-methylanatabine 4, (S)-anabasine 5, and (S)-N-methylanabasine 6, known as natural products in tobacco, was established from a common chiral homoallylic (S)-3-(1-azido-but-3-enyl)-pyridine 15. An intramolecular hydroboration-cycloalkylation of the homoallylic azide intermediate

  对映体的六个哌啶和吡咯烷生物碱，（S）-去甲烟碱1，（S）-烟碱2，（S）-安那他滨3，（S）-N-甲基安那他滨4，（S）-天麻碱5和（S ）-N-甲基天麻碱6，是烟草中的天然产物，是由一种常见的手性均聚物（S）-3-（1-叠氮基-丁-3-烯基）-吡啶15建立的。该均聚物的分子内氢硼化-环烷基化叠氮化物中间体15是吡咯烷环形成中的关键步骤。二亚乙基胺中间体（S）-烯丙基-（1-吡啶-3-基-丁-3-烯基）-氨基甲酸苄酯20的闭环复分解反应（RCM）是哌啶环形成中的关键步骤。从市售的3-吡啶甲醛13中，描述了一种简便，简便的烟草生物碱对映体合成方法：（S）-去甲烟碱1（5个步骤，
• Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols
  作者：Satwinder Singh、Subodh Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0957-4166(02)00743-7

  日期：2002.12

  A chemoenzymatic methodology has been developed using indium-mediated allylation of heterocyclic aldehydes under aqueous conditions followed by Pseudomonas cepacia lipase-catalyzed enantioselective acylation of racemic homoallylic and homopropargylic alcohols in organic media. It is observed that the lipase immobilized on ceramic particles (PS-C Amano II) catalyzes the resolution in a highly enantioselective

  已开发出一种化学酶学方法，该方法是在水性介质中使用铟介导的杂环醛的烯丙基化烯丙基化，然后在有机介质中假单胞菌cepcia脂肪酶催化外消旋均烯丙基和均炔丙醇的对映选择性酰化。观察到，与天然酶（PS Amano）相比，固定在陶瓷颗粒上的脂肪酶（PS-C Amano II）以更少的时间以高对映选择性的方式催化拆分。该方法提供了新的功能化手性合成子，可用于合成天然和假天然产物。
• Diversity-Oriented Synthesis of Pochonins and Biological Evaluation against a Panel of Kinases
  作者：Emilie Moulin、Sofia Barluenga、Frank Totzke、Nicolas Winssinger

  DOI：10.1002/chem.200600553

  日期：2006.11.24

  14-membered resorcylic acid lactones. As there are a high number of ATPase and kinase inhibitors among natural resorcylic lactones, a library based on the pochonin scaffold, with five points of diversity, was prepared which includes diversity beyond that of the natural analogues. The library was synthesized by using solid-supported reagents amenable to automation. Testing the library for its inhibition

  Pochonins AF最近被表征为自然存在的14元间苯二酸内酯家族的6个新成员。由于天然间苯二酚内酯中存在大量的ATPase和激酶抑制剂，因此建立了基于软骨素支架的文库，该文库具有五个多样性点，其中包括超出天然类似物的多样性。该文库是通过使用适合自动化的固体支持试剂合成的。测试该文库在10 microM下对一组24种激酶的抑制作用后，命中率> 14％。这些结果证明了间苯二酚对抑制治疗相关激酶的潜力。
• An efficient route for the allylation of arylaldehydes to give enantiopure homoallylic alcohols
  作者：Prashant B. Thorat、Santosh V. Goswami、Sudhakar R. Bhusare

  DOI：10.1016/j.tetasy.2013.08.016

  日期：2013.10

  An efficient asymmetric synthesis of homoallylic alcohols is described by the allylation of carbonyl compounds using organocatalysts as chiral directors in the presence of tin metal. The effect of chiral environment is also studied on the allylation reactions. This method allows us to obtain two different enantiomers of homoallylic alcohol in the presence of the corresponding chiral compound. The protocol is applied to various aldehydes to obtain high yields and excellent enantioselectivities for the corresponding homoallylic alcohols. (C) 2013 Elsevier Ltd. All rights reserved.
• Chiral synthesis via organoboranes. 36. Exceptionally enantioselective allylborations of representative heterocyclic aldehydes at -100 .degree.C under salt-free conditions
  作者：Uday S. Racherla、Yi Liao、Herbert C. Brown

  DOI：10.1021/jo00050a045

  日期：1992.11

  Chiral terpenyl-based allylborane reagents (Ter2*BCH2CH=CH2, 1-3) undergo facile condensation with representative heterocyclic aldehydes (HetCHO) at -100-degrees-C (in the absence of Mg2+ salts) and afford the corresponding homoallylic alcohols (HetCH*(OH)CH2CH=CH2,12-19) in enantiomeric purities approaching 100% ee. A new workup procedure involving 8-hydroxyquinoline (8-HQ) has been utilized for the convenient isolation of the product alcohols.