(R)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol | 943859-09-4

• 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)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol
• 英文别名: (3R)-6-[(4-methoxyphenyl)methoxy]hex-1-yn-3-ol
• CAS: 943859-09-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: XNLBTHWUTYRZFL-ZDUSSCGKSA-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：
  7
• 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：

  (R)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol 在 咪唑 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 10.75h， 生成 (R)-((S)-1-((4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)octyl) 4-hydroxyhex-5-ynoate
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

  摘要：

  Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful exploration of a ring closing metathesis (RCM) reaction. 2-Propylthiophene was used as a masked synthon for n-heptyl glycoside, which served as main source for one of the RCM precursors and accessed by reductive desulfurization (Mozingo type reduction) of an appropriately substituted thiophene ribofuranoside. The other RCM precursor was accessed by applying an enzymatic kinetic resolution/Mitsunobu inversion sequence to an alkyne alcohol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.001
• 作为产物：
  描述：

  4-[(4-甲氧基苯基)甲氧基]丁醛 在 甲醇 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 Candida antarctica lipase immobilizedon acrylic resin 、 potassium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 异丙醚 为溶剂， 反应 23.67h， 生成 (R)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

  摘要：

  Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful exploration of a ring closing metathesis (RCM) reaction. 2-Propylthiophene was used as a masked synthon for n-heptyl glycoside, which served as main source for one of the RCM precursors and accessed by reductive desulfurization (Mozingo type reduction) of an appropriately substituted thiophene ribofuranoside. The other RCM precursor was accessed by applying an enzymatic kinetic resolution/Mitsunobu inversion sequence to an alkyne alcohol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.001

文献信息

• Total Synthesis of Citrafungin A
  作者：Susumi Hatakeyama、Mumen F. A. Amer、Keisuke Takahashi、Jun Ishihara

  DOI：10.3987/com-06-s(k)44

  日期：——
• New marine prostanoids, preclavulone lactones, from the Okinawan soft coral Clavularia viridis
  作者：Makoto Iwashima、Kinzo Watanabe、Kazuo Iguchi

  DOI：10.1016/s0040-4039(97)10211-8

  日期：1997.12

  Two new marine prostanoids, preclavulone lactones I (1) and II (2) were isolated from the Okinawan soft coral, Clavularia viridis. Their structures were determined based on spectroscopic analysis and chemical synthesis from (S)-malic acid. Preclavulone Lactones with side chains having absolute configurations opposite to those of mammalian prostanoids could be recognized as key intermediates in biosynthesis of clavulones. (C) 1997 Elsevier Science Ltd.