6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol | 197219-15-1

• 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: 6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol
• 英文别名: 6-(4-methoxybenzyloxy)-2-hexyn-1-ol；6-[(4-Methoxyphenyl)methoxy]hex-2-yn-1-ol
• CAS: 197219-15-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: NNBMCSFSSVKIPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 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：

  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
• 作为产物：
  描述：

  4-甲氧基苄醇 在 正丁基锂 、 氢溴酸 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 62.34h， 生成 6-[(4-methoxyphenyl)methoxy]-2-hexyn-1-ol
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Swainsonine, (+)-1,2-Di-epi-swainsonine, and (+)-1,2,8-Tri-epi-swainsonine

  摘要：

  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.

  DOI：

  10.1021/jo025977w

文献信息

• Transformation of cis-Epoxy Compound to cis-2,3-Disubstituted Oxane and Investigation on Propagation Step in the Ring-Expansion Reactions of cis,trans-Diepoxy Systems
  作者：Nobuyuki Hayashi、Hiroko Noguchi、Sadao Tsuboi

  DOI：10.1016/s0040-4020(00)00622-0

  日期：2000.9

  Conversion of cis-epoxy compounds by successive ring-expansion reaction into trans-fused cyclic ethers was examined from both the initiation step and the propagation step. The ring-expansion reaction of cis-4,5-epoxy compounds containing a leaving group on C-1 was attempted as a unit process for the successive reaction. When a chloromesyl group was used as a leaving group, the ring expansion proceeded to give an oxane derivative (endo-type product) preferentially. On the other hand, investigation of the propagation step was carried out with respect to epoxy oxane derivatives. It was clarified that the ring-expansion reaction of cis-2,3-disubstituted oxane derivatives provided spiro acetals as products, not the desired trans-fused cyclic ethers, owing to the reaction pathway triggered by 1,2-hydride rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.
• The biomimetic construction of fused cyclic polyethers
  作者：Nobuyuki Hayashi、Kenshu Fujiwara、Akio Murai

  DOI：10.1016/s0040-4020(97)00780-1

  日期：1997.9

  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.
• Stereocontrolled synthesis of (+)-lycoperdic acid based on a palladium catalyzed reaction using a serine-derived organozinc reagent
  作者：Hidekazu Masaki、Tomoko Mizozoe、Tomoyuki Esumi、Yoshiharu Iwabuchi、Susumi Hatakeyama

  DOI：10.1016/s0040-4039(00)00719-x

  日期：2000.6

  An efficient stereocontrolled synthesis of (+)-lycoperdic acid has been achieved based on palladium catalyzed cross-coupling reaction of (Z)-1-(tert-butyldimethylsiloxy)-3-iodo-6-(p-methoxybenzyl)oxy-2-hexane with the organozinc reagent, prepared from N-Boc-beta-iodoalanine methyl eater. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.