(S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentan-1-ol | 794588-83-3

• 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: (S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentan-1-ol
• 英文别名: 3-(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)pentan-1-ol
• CAS: 794588-83-3
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: NFGKRTDSHGHAQP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentan-1-ol 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 25.0h， 生成 1-allyl-1H-indole-2-carboxylic acid 1-(2-allyloxyethyl)-3-(4-methoxybenzyloxy)propyl ester
  参考文献：
  名称：

  Ring-closing metathesis: a powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

  摘要：

  Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.146
• 作为产物：
  描述：

  (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]pentanal 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以92%的产率得到(S)-3-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)pentan-1-ol
  参考文献：
  名称：

  Ring-closing metathesis: a powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

  摘要：

  Based on our synthetic strategy developed for the total synthesis of the macrocyclic salicylate natural product salicylihalamide, we describe herein the synthesis of a series of simplified salicylihalamide-based analogs. Alterations in the aromatic fragment, the macrolactone scaffold and side-chain were evaluated for in vitro inhibition of V-ATPase activity and human tumor cell growth. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.146

文献信息

• Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level
  作者：Xin Gao、Yong Jian Zhang、Michael J. Krische

  DOI：10.1002/anie.201008296

  日期：2011.4.26

  α‐trifluoromethyl allyl benzoate to alcohols in the presence of an ortho‐cyclometalated iridium catalyst results in the generation of aldehyde–allyliridium intermediates to form enantiomerically enriched products of anti‐(α‐trifluoromethyl)allylation. An identical set of products is obtained from aldehydes under related transfer hydrogenation conditions employing isopropyl alcohol as terminal reductant.

  氟的繁荣：在邻位环金属化铱催化剂存在下，将 α-三氟甲基烯丙基苯甲酸酯暴露于醇中，导致生成醛-烯丙基铱中间体，形成富含对映异构体的反-（α-三氟甲基）烯丙基化产物。在使用异丙醇作为末端还原剂的相关转移氢化条件下，由醛获得一组相同的产物。