(2Z)-4-methoxyoct-2-en-1-ol | 916758-25-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z)-4-methoxyoct-2-en-1-ol
• 英文别名: (Z)-4-methoxyoct-2-en-1-ol
• CAS: 916758-25-3
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: JOCWIUROBUGEHP-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2Z)-4-methoxyoct-2-en-1-ol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以66%的产率得到(2Z)-1-bromo-4-methoxyoct-2-ene
  参考文献：
  名称：

  A facile method for the stereoselective preparation of (1E,3E)-4-substituted-1-amino-1,3-dienes via 1,4-elimination

  摘要：

  The 1,4-elimination reaction of 1-amino-4-methoxy-(2Z) -alkenes is shown to proceed with high (1E,3E)-stereoselectivities to afford the corresponding 4-substituted-1-amino-1,3-dienes in good yield. The scope and stereochemical features of the synthetic method are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.140
• 作为产物：
  描述：

  (Z)-1-(2-ethoxyethoxy)-4-methoxyoct-2-ene 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (2Z)-4-methoxyoct-2-en-1-ol
  参考文献：
  名称：

  烯丙基1,3-二烯基醚的简便且立体选择性的合成方法

  摘要：

  1-烯丙氧基-4-甲氧基-（2 Z）-烯烃与正丁基锂的1,4-消除反应显示出明显优先于[2,3] Wittig重排以提供烯丙基（1 Z高立体选择性的，3 E）-二烯基醚。由此获得的二烯基醚的克莱森重排证明了该方法的合成效用。

  DOI：

  10.1016/j.tetlet.2006.08.100

文献信息

• Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for α-(N-Boc-2-pyrrolidinyl) aldehydes
  作者：Eiji Tayama、Seijun Otoyama、Wataru Isaka

  DOI：10.1039/b806492j

  日期：——

  The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines (1) is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines (2); the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (2) provides α-(N-Boc-2-pyrrolidinyl) aldehydes (3) in excellent yields with high α-regioselectivities.

  (Z)-N-Boc-2-(4-甲氧基-2-烯丙氧基)吡咯烷（1）的1,4-消除反应表现出高度的（1E,3E）-立体选择性，生成N-Boc-2-(1,3-二烯氧基)吡咯烷（2）；布朗斯特酸催化的N-Boc-2-(1,3-二烯氧基)吡咯烷（2）的氮杂-费里尔反应在优异的产率下提供了具有高α-区域选择性的α-(N-Boc-2-吡咯烷基)醛（3）。
• 1,4-Elimination/Brønsted acid catalyzed aza-Ferrier reaction sequence as an entry to β-amino-β,γ-unsaturated aldehydes
  作者：Eiji Tayama、Kouki Horikawa、Hajime Iwamoto、Eietsu Hasegawa

  DOI：10.1016/j.tet.2013.01.088

  日期：2013.4

  The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)amines with Bronsted acids catalyzed aza-Ferrier reaction of the 1,4-eliminated product, thus obtained, afforded various beta-amino-beta,gamma-unsaturated aldehydes. The scope and limitation of this sequential reaction are described. (C) 2013 Elsevier Ltd. All rights reserved.
• Regio- and Stereoselective Ferrier Reaction of <i>O</i>-1,3-Dienyl Acetals Promoted by Organoaluminum Complexes
  作者：Eiji Tayama、Wataru Isaka

  DOI：10.1021/ol062042j

  日期：2006.11.1

  The Ferrier reaction of O-1,3-dienyl acetals promoted by organoaluminum complexes such as methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) is shown to proceed with a high degree of regio- and stereoselectivity to afford the corresponding alpha-alkenyl-substituted beta-alkoxy aldehydes in good yields. The mechanistic origin of the high regiocontrolling ability of MAD is elucidated. This method, coupled with the easy availability of the requisite substrates, expands the synthetic scope of the Ferrier reaction.
• Regioselective synthesis of secondary 1,3-dienamides by successive eliminations
  作者：Eiji Tayama、Shun Saito

  DOI：10.1016/j.tet.2015.11.065

  日期：2016.2

  The regioselective synthesis of secondary 1,3-dienamides 3 (1-N-acylamino-1,3-dienes) is successfully demonstrated by regiospecific base -promoted 1,4 -elimination of (Z)- or (E)-N,N-di-Boc-4-methoxy-2-buten-1 -ylamine 1 followed by mono-Boc elimination in situ. (C) 2015 Elsevier Ltd. All rights reserved,