(2E)1-苄氧基-2-甲基-2-丁烯-4-醇 | 62311-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2E)1-苄氧基-2-甲基-2-丁烯-4-醇
• 英文名称: (2E) 1-benzyloxy-2-methyl-2-buten-4-ol
• 英文别名: 4-benzyloxy-3-methyl-but-2-en-1-ol；4-benzyloxy-3-methylbut-2-en-1-ol；4-Benzyloxy-3-methyl-2-buten-1-ol；(E)-3-methyl-4-phenylmethoxybut-2-en-1-ol
• CAS: 62311-52-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: XMVUEHYAOORWLV-YRNVUSSQSA-N

物化性质

• 沸点：
  310.3±30.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)1-苄氧基-2-甲基-2-丁烯-4-醇 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 氢气 、 (+)-Weinsaeure-diethylester 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.25h， 生成 2-C-甲基-赤藓糖醇
  参考文献：
  名称：

  Simple and versatile synthesis of branched polyols: (+)-2-C-methylerythritol and (+)-2-C-methylthreitol

  摘要：

  The paper reports a new approach for the enantioselective synthesis of 2-C-methyl tetrols. The procedure has been utilized for preparing methylthreitol and methylerythritol, a putative intermediate in the mevalonate-independent biosynthesis of terpenoids in bacteria, algae and higher plants. The methodology offers straightforward access to related compounds and isotopically labeled derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01296-x
• 作为产物：
  描述：

  异戊烯醇 在 咪唑 、 叔丁基过氧化氢 、 selenium(IV) oxide 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.5h， 生成 (2E)1-苄氧基-2-甲基-2-丁烯-4-醇
  参考文献：
  名称：

  Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction

  摘要：

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.

  DOI：

  10.1021/ja068077w

文献信息

• Construction of a Chiral Quaternary Carbon Center via 1,2-Acyl Migration of an Optically Active α,β-Epoxy Ketone
  作者：Kunisuke Okada、Toshiyuki Katsura、Hideo Tanino、Hisae Kakoi、Shoji Inoue

  DOI：10.1246/cl.1994.157

  日期：1994.1

  The construction of a chiral building block with a quaternary carbon center is described, based on the Lewis acid-catalyzed acyl migration of α,β-epoxy ketone with alkyl and alkenyl substituents.

  基于具有烷基和烯基取代基的 α,β-环氧酮的路易斯酸催化酰基迁移，描述了具有季碳中心的手性构件的构建。
• IspG Converts an Epoxide Substrate Analogue to (<i>E</i>)-4-Hydroxy-3-methylbut-2-enyl Diphosphate: Implications for IspG Catalysis in Isoprenoid Biosynthesis
  作者：Rodney L. Nyland II、Youli Xiao、Pinghua Liu、Caren L. Freel Meyers

  DOI：10.1021/ja907470n

  日期：2009.12.16

  IspG is an intriguing enzyme in bacteria, parasite, and plant isoprenoid biosynthesis, and its catalytic mechanism remains elusive. We report here the synthesis of (2R,3R)-4-hydroxy-3-methyl-2,3-epoxybutanyl diphosphate (Epoxy-HMBPP), a proposed intermediate in one of the frequently cited mechanistic models. We have also demonstrated that this epoxide analogue is a catalytically competent IspG substrate. This study represents the first mechanistic study of this important enzyme.
• Convergent Enantioselective Synthesis of the Tricyclic Core of Phomactin A
  作者：Peter J. Mohr、Randall L. Halcomb

  DOI：10.1021/ol026159t

  日期：2002.7.1

  [GRAPHICS]The tricyclic core of phomactin A was synthesized from 6,6-dimethyl-2-cyclohexen-1-one. Key reactions include the addition of a cyclohexenyllithium reagent to an epoxyaldehyde and a regioselective intramolecular epoxide opening to install the oxadecalin core.
• Concise Synthesis of (+)-2-<i>C</i>-Methyl-<scp>d</scp>-erythritol-4-phosphate
  作者：Angelo Fontana

  DOI：10.1021/jo005732o

  日期：2001.4.1
• Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction
  作者：Jennifer M. Schomaker、Andrea R. Geiser、Rui Huang、Babak Borhan

  DOI：10.1021/ja068077w

  日期：2007.4.1

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.