1-allyl-1H-indole-2-carboxylic acid 1-(2-allyloxyethyl)-3-(4-methoxybenzyloxy)propyl ester | 794588-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-allyl-1H-indole-2-carboxylic acid 1-(2-allyloxyethyl)-3-(4-methoxybenzyloxy)propyl ester
• 英文别名: [(3R)-1-[(4-methoxyphenyl)methoxy]-5-prop-2-enoxypentan-3-yl] 1-prop-2-enylindole-2-carboxylate
• CAS: 794588-64-0
• 化学式: C₂₈H₃₃NO₅
• 分子量: 463.574
• InChiKey: GIUQYEIKDRMLEB-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-allyl-1H-indole-2-carboxylic acid 1-(2-allyloxyethyl)-3-(4-methoxybenzyloxy)propyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 6.3h， 生成 12-[2-(4-methoxybenzyloxy)ethyl]-5,8,11,12-tetrahydro-10H-9,13-dioxa-4b-azacyclododeca[a]inden-14-one 、 12-[2-(4-methoxybenzyloxy)ethyl]-5,8,11,12-tetrahydro-10H-9,13-dioxa-4b-azacyclododeca[a]inden-14-one
  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 、 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 、 乙醇 为溶剂， 反应 25.75h， 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

文献信息

• Ring-closing metathesis: a powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors
  作者：Sylvain Lebreton、Xiao-Song Xie、Deborah Ferguson、Jef K. De Brabander

  DOI：10.1016/j.tet.2004.06.146

  日期：2004.10

  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.