(1S)-1-[6-[(1R)-1-hydroxybut-3-enyl]pyridin-2-yl]but-3-en-1-ol | 184896-41-1

• 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: (1S)-1-[6-[(1R)-1-hydroxybut-3-enyl]pyridin-2-yl]but-3-en-1-ol
• CAS: 184896-41-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: XAJDSIMFYUMAHF-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 (1S)-1-[6-[(1R)-1-hydroxybut-3-enyl]pyridin-2-yl]but-3-en-1-ol 在 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 以33%的产率得到2,16-Bis(prop-2-enyl)-3,6,9,12,15-pentaoxa-21-azabicyclo[15.3.1]henicosa-1(21),17,19-triene
  参考文献：
  名称：

  New Pyridino-18-crown-6 Ligands Containing Two Methyl, Two tert-Butyl, or Two Allyl Substituents on Chiral Positions Next to the Pyridine Ring

  摘要：

  Chiral 2,16-diallyl-, 2,16-dimethyl-, and 2,16-di-tert-butylpyridino-18-crown-6 Ligands have been. prepared by treating the appropriate chiral alpha,alpha'-disubstituted pyridinedimethanol with tetraethylene glycol ditosylate in the presence of base. In these reactions, chiral 2:2 dimers (dipyridino-36-crown-12 derivatives) were also obtained. The log K values for the interaction of these chiral ligands with the enantiomers of (alpha-phenylethyl)ammonium perchlorate (PhEt) and (alpha-(1-naphthyl)ethyl)-ammonium perchlorate (NapEt) were measured using an H-1 NMR titration method in a CDCl3/CD3OD (1/1) solvent mixture. The log K values indicate that these chiral pyridino-18-crown-6 ligands have high complexing abilities and some enantiomeric recognition for the chiral organic ammonium perchlorates. The H-1 NMR titration experiments also show that the phenyl ring of the guest PhEt is approximately parallel to the pyridine ring in the chiral diallyl- and dimethyl-substituted Ligand complexes with chiral PhEt and the phenyl ring is perpendicular to the pyridine ring in the chiral di-tert-butyl-substituted ligand complex with PhEt. These results were supported by MM2 calculations.

  DOI：

  10.1021/jo960474+
• 作为产物：
  描述：

  吡啶-2,6-二甲醛 、 (-)-B-二异松莰烯基烯丙基硼 以 四氢呋喃 为溶剂， 生成 (1S)-1-[6-[(1R)-1-hydroxybut-3-enyl]pyridin-2-yl]but-3-en-1-ol 、 (S,S)-α,α'-diallyl-2,6-pyridinedimethanol
  参考文献：
  名称：

  通过有机ob酸酯的手性合成。46.从对映体纯的C（2）-对称的吡啶-和噻吩二醇（1）高效制备手性吡啶和噻吩-18-皇冠-6配体。

  摘要：

  与B-chlorodiisopinocampheylborane不对称还原2,6-二酰基吡啶提供非常高的de和ee中相应的C（2）对称二醇。2，6-吡啶二甲醛和2，5-噻吩二甲醛的不对称烯丙基硼化以非常高的de和ee提供了相应的双均烯丙基醇。将这些旋光纯的二醇转化为二钠盐或二钾盐，并用四（乙二醇）二甲苯磺酸酯处理以获得相应的手性吡啶基和噻吩-18-冠-6配体。但是，全氟烷基二醇不能提供大环。

  DOI：

  10.1021/jo980899r

文献信息

• Efficient Synthesis of Enantiomerically Pure C2-Symmetric Diols via the Allylboration of Appropriate Dialdehydes
  作者：P.Veeraraghavan Ramachandran、Guang-Ming Chen、Herbert C. Brown*

  DOI：10.1016/s0040-4039(97)00414-0

  日期：1997.4

  The reaction of the enantiomers of B-allyidiisopinocampheylborane with 1,2-, 1,3-, and 1,4-benzenedialdehydes, 2,6-pyridinedicarboxaldehyde, glyoxal, and glutaric dialdehyde, provides the corresponding enantiomers of the bis-homoallylic alcohols in 88-98% de, and greater than or equal to 98% ee. (C) 1997 Elsevier Science Ltd.
• Chiral Synthesis via Organoboranes. 46. An Efficient Preparation of Chiral Pyridino- and Thiopheno-18-crown-6 Ligands from Enantiomerically Pure <i>C</i>₂-Symmetric Pyridine- and Thiophenediols¹
  作者：Guang-Ming Chen、Herbert C. Brown、P. Veeraraghavan Ramachandran

  DOI：10.1021/jo980899r

  日期：1999.2.1

  high de and ee. Asymmetric allylboration of 2,6-pyridinedicarboxaldehyde and 2,5-thiophenedicarboxaldehyde provides the corresponding bis-homoallylic alcohols in very high de and ee. These optically pure diols were converted to the disodium or dipotassium salts and treated with tetra(ethylene glycol) ditosylate to obtain the corresponding chiral pyridino and thiopheno-18-crown-6 ligands. However, the

  与B-chlorodiisopinocampheylborane不对称还原2,6-二酰基吡啶提供非常高的de和ee中相应的C（2）对称二醇。2，6-吡啶二甲醛和2，5-噻吩二甲醛的不对称烯丙基硼化以非常高的de和ee提供了相应的双均烯丙基醇。将这些旋光纯的二醇转化为二钠盐或二钾盐，并用四（乙二醇）二甲苯磺酸酯处理以获得相应的手性吡啶基和噻吩-18-冠-6配体。但是，全氟烷基二醇不能提供大环。
• New Pyridino-18-crown-6 Ligands Containing Two Methyl, Two <i>tert</i>-Butyl, or Two Allyl Substituents on Chiral Positions Next to the Pyridine Ring
  作者：Yoichi Habata、Jerald S. Bradshaw、J. Jolene Young、Steven L. Castle、Peter Huszthy、Tongjin Pyo、Milton L. Lee、Reed M. Izatt

  DOI：10.1021/jo960474+

  日期：1996.1.1

  Chiral 2,16-diallyl-, 2,16-dimethyl-, and 2,16-di-tert-butylpyridino-18-crown-6 Ligands have been. prepared by treating the appropriate chiral alpha,alpha'-disubstituted pyridinedimethanol with tetraethylene glycol ditosylate in the presence of base. In these reactions, chiral 2:2 dimers (dipyridino-36-crown-12 derivatives) were also obtained. The log K values for the interaction of these chiral ligands with the enantiomers of (alpha-phenylethyl)ammonium perchlorate (PhEt) and (alpha-(1-naphthyl)ethyl)-ammonium perchlorate (NapEt) were measured using an H-1 NMR titration method in a CDCl3/CD3OD (1/1) solvent mixture. The log K values indicate that these chiral pyridino-18-crown-6 ligands have high complexing abilities and some enantiomeric recognition for the chiral organic ammonium perchlorates. The H-1 NMR titration experiments also show that the phenyl ring of the guest PhEt is approximately parallel to the pyridine ring in the chiral diallyl- and dimethyl-substituted Ligand complexes with chiral PhEt and the phenyl ring is perpendicular to the pyridine ring in the chiral di-tert-butyl-substituted ligand complex with PhEt. These results were supported by MM2 calculations.