(S)-acetic acid 2-(quinolin-4-yl)-3-(trityloxy)propyl ester | 526203-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-acetic acid 2-(quinolin-4-yl)-3-(trityloxy)propyl ester
• CAS: 526203-37-2
• 化学式: C₃₃H₂₉NO₃
• 分子量: 487.598
• InChiKey: BDYCMRLHXFTDHL-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-acetic acid 2-(quinolin-4-yl)-3-(trityloxy)propyl ester 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-4-[1-(p-methoxyphenoxymethyl)-2-(trityloxy)ethyl]quinoline
  参考文献：
  名称：

  O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines

  摘要：

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00711-5
• 作为产物：
  描述：

  三苯基氯甲烷 、 [(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(S)-acetic acid 2-(quinolin-4-yl)-3-(trityloxy)propyl ester
  参考文献：
  名称：

  O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines

  摘要：

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00711-5

文献信息

• Enzymatically Asymmetrised Chiral Building Blocks for the Synthesis of Complex Natural Product Analogues: The Synthesis of Dynemicin Analogues from 2-(Quinolin-4-yl)propane-1,3-diol
  作者：Renata Riva、Luca Banfi、Andrea Basso、Valentina Gandolfo、Giuseppe Guanti

  DOI：10.1002/ejoc.200901478

  日期：2010.5

  Full details of our synthetic approaches directed towards the enantioselective synthesis of new dynemicin analogues each containing a side-arm (a “handle”) incorporating a protected alcohol are reported.

  报告了我们的合成方法的全部细节，这些方法针对新动力霉素类似物的对映选择性合成，每个类似物都包含一个侧臂（“手柄”），并结合了受保护的醇。
• O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines
  作者：Giuseppe Guanti、Sara Perrozzi、Renata Riva

  DOI：10.1016/s0957-4166(02)00711-5

  日期：2002.12

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.