(2E)-6-(4-methoxybenzyloxy)-2-hexen-1-ol | 197219-35-5

• 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: (2E)-6-(4-methoxybenzyloxy)-2-hexen-1-ol
• 英文别名: 6-(4-methoxybenzyloxy)hex-2-en-1-ol；6-(4-methoxybenzyloxy)-trans-hex-2-en-1-ol；6-[(4-methoxyphenyl)methoxy]-(E)-2-hexen-1-ol；(E)-6-(4-methoxybenzyloxy)hex-2-en-1-ol；(E)-6-[(4-methoxyphenyl)methoxy]hex-2-en-1-ol
• CAS: 197219-35-5
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: WLUMDRZGAKRQFU-DUXPYHPUSA-N

物化性质

• 沸点：
  365.9±42.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-6-(4-methoxybenzyloxy)-2-hexen-1-ol 在 正丁基锂 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.58h， 生成 (5E)-9-(4-methoxybenzyloxy)-1-(oxan-2-yloxy)-5-nonen-2-yne
  参考文献：
  名称：

  The biomimetic construction of fused cyclic polyethers

  摘要：

  The formation of fused cyclic ethers by biomimetic synthesis was demonstrated. The one-pot successive ring-expansion reactions of bromo diepoxides were investigated by regarding the epoxy groups as the nucleophiles for the intramolecular cationic carbons to obtain the fused cyclic ethers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00780-1
• 作为产物：
  描述：

  6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以100%的产率得到(2E)-6-(4-methoxybenzyloxy)-2-hexen-1-ol
  参考文献：
  名称：

  The biomimetic construction of fused cyclic polyethers

  摘要：

  The formation of fused cyclic ethers by biomimetic synthesis was demonstrated. The one-pot successive ring-expansion reactions of bromo diepoxides were investigated by regarding the epoxy groups as the nucleophiles for the intramolecular cationic carbons to obtain the fused cyclic ethers. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00780-1

文献信息

• An improved two-step synthetic route to primary allylic alcohols from aldehydes
  作者：Zheng Liu、Yaqiong Gong、Hoe-Sup Byun、Robert Bittman

  DOI：10.1039/b9nj00710e

  日期：——

  An improved two-step synthetic route to allylic alcohols from aldehydes has been developed. A modification of the HWE reaction in H2O–2-PrOH (1 ∶ 1) and a convenient protocol to prepare AlH3 in THF from LiAlH4 and n-BuBr are the key factors in the improvement.

  开发出一种从醛合成烯丙醇的改进两步合成路线。在H2O–2-PrOH（1∶1）中对HWE反应的改良，以及从LiAlH4和n-BuBr在THF中制备AlH3的简便方案，是改进的关键因素。
• Asymmetric Synthesis of Both the Enantiomers of <i>trans</i>-3-Hydroxypipecolic Acid
  作者：Pradeep Kumar、Mandar S. Bodas

  DOI：10.1021/jo0485381

  日期：2005.1.1

  Both the enantiomers of trans-3-hydroxypipecolic acid have been synthesized employing the Sharpless asymmetric dihydroxylation and epoxidation as the key steps starting from a commercially available starting material 1,4-butanediol.

  反式-3-羟基哌酸的两种对映异构体均以Sharpless不对称二羟基化和环氧化为关键步骤，从市售的原料1，4-丁二醇开始合成。
• Studies toward the Total Synthesis of Vinigrol. Synthesis of the Octalin Ring
  作者：Louis Morency、Louis Barriault

  DOI：10.1021/jo051318i

  日期：2005.10.1

  Herein, we disclose our results regarding various strategies toward the assembly of the octanyl ring of vinigrol. Attempts to generate the problematic eight-membered ring through a ring expansion or via unification of the terminal olefins using the ring-closing metathesis were not successful. The cyclooctane ring was created via a sequential hydroxy Diels−Alder/Claisen rearrangement reaction of diene

  在本文中，我们公开了有关长春新酚辛烷环组装的各种策略的结果。通过开环或通过使用闭环易位的末端烯烃的统一来产生有问题的八元环的尝试是不成功的。环辛烷环是通过二烯55和N-苄基马来酰亚胺的连续羟基Diels-Alder / Claisen重排反应生成的。
• Asymmetric Synthesis of (−)-Swainsonine, (+)-1,2-Di-<i>epi</i>-swainsonine, and (+)-1,2,8-Tri-<i>epi</i>-swainsonine
  作者：Karl B. Lindsay、Stephen G. Pyne

  DOI：10.1021/jo025977w

  日期：2002.11.1

  The asymmetric synthesis of H-swainsonine via a nonchiral pool route that involves the Sharpless epoxidation to induce chirality is reported. The key steps involve vinyl epoxide aminolysis, ring-closing metathesis, and intramolecular N-alkylation to prepare the indolizidine ring and a highly diastereoselective cis-dihydroxylation using AD-mix-cc. This synthetic strategy also allowed for the diastereoselective synthesis of (+)-1,2-di-epi-swainsonine and (+)-1,2,8-tri-epi-swainsonine.
• An efficient protocol for the preparation of MOM ethers and their deprotection using zirconium(IV) chloride
  作者：G.V.M. Sharma、K. Laxma Reddy、P. Sree Lakshmi、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2004.10.091

  日期：2004.12

  An efficient protocol for the preparation of MOM ethers from alcohols and formaldehyde dimethyl acetal (DMFA) using ZrCl4 (10 mol%) at room temperature under solvent free conditions has been developed. Similarly, the same Lewis acid, ZrCl4 (50 mol%), in isopropanol at reflux was utilised for the deprotection of MOM ethers. (C) 2004 Elsevier Ltd. All rights reserved.