(R)-2-benzyloxy-1-butanol | 84994-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-benzyloxy-1-butanol
• 英文别名: (R)-2-(benzyloxy)butan-1-ol；(2R)-2-(Benzyloxy)butan-1-ol；(2R)-2-phenylmethoxybutan-1-ol
• CAS: 84994-62-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: JRQIUTBHFLCSIT-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+)-(R)-2-(benzyloxy)butanal 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-benzyloxy-1-butanol
  参考文献：
  名称：

  Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

  摘要：

  Treatment of a range of O-protected glycolate derivatives of the chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with KHMDS in the presence of 18-crown-6 followed by addition of an alkyl halide generates alpha-substituted derivatives with very high levels of diastereoselectivity. Alternatively, reaction of the potassium enolate of a propanoate or O-protected glycolate derivative of N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine with a range of aldehydes gives syn-aldol products with high levels of diastereoselectivity. These adducts may be reductively cleaved with LiAlH(4) to give enantiopure alpha-alkoxy-, alpha-substituted-beta-alkoxy- and alpha,beta-dialkoxyaldehydes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.105

文献信息

• Studies toward the synthesis of pinnatoxins: the spiroimine fragment
  作者：Craig E. Stivala、Armen Zakarian

  DOI：10.1016/j.tetlet.2007.07.182

  日期：2007.9

  An enantioselective approach to the spiroimine fragment of pinnatoxins is described. The strategy is based on a recently developed diastereoselective Ireland–Claisen rearrangement to establish the challenging congested quaternary and tertiary stereocenters within the cyclohexene ring.

  描述了对pinnatoxins的spiroimine片段的对映选择性方法。该策略基于最近开发的非对映选择性爱尔兰-克莱森重排法，以在环己烯环内建立具有挑战性的拥挤的四级和三级立体中心。
• AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER—AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF<i>exo</i>-(+)-BREVICOMIN—
  作者：Masatoshi Asami、Teruaki Mukaiyama

  DOI：10.1246/cl.1983.93

  日期：1983.1.5

  α-Benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents. The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.

  通过用氢化二异丁基铝（DIBAL-H）和格氏试剂连续处理 2-甲氧基羰基-3-苯基-1,3-二氮杂双环[3.3.0]辛烷，合成出对映体过量的、在 α 碳原子上具有手性叔中心的 α-苄氧基醛。该不对称反应被用于外-(+)-brevicomin 的全合成。
• Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Asymmetric Hydrogenation of α-Aryloxy Aldehydes via Dynamic Kinetic Resolution
  作者：Zhang-Tao Zhou、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1002/adsc.200800634

  日期：2009.2

  Abstractmagnified imageA catalytic enantioselective hydrogenation of racemic α‐aryloxy aldehydes via dynamic kinetic resolution has been developed by using (diamine)(spirodiphosphine)ruthenium(II) chloride [RuCl2(SDPs)(diamine)] catalysts. Employing this new reaction system a variety of optically active β‐aryloxy primary alcohols were synthesized in high yields and moderate to good enantioselectivities.
• Helmchen, Guenter; Wierzchowski, Reiner, Angewandte Chemie, 1984, vol. 96, # 1, p. 59 - 60
  作者：Helmchen, Guenter、Wierzchowski, Reiner

  DOI：——

  日期：——
• HELMCHEN, G.;WIERZCHOWSKI, R., ANGEW. CHEM., 1984, 96, N 1, 59-60
  作者：HELMCHEN, G.、WIERZCHOWSKI, R.

  DOI：——

  日期：——