(S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanol | 718629-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanol
• 英文别名: (3S)-4-[tert-butyl(dimethyl)silyl]oxy-3-quinolin-4-ylbutan-1-ol
• CAS: 718629-28-8
• 化学式: C₁₉H₂₉NO₂Si
• 分子量: 331.53
• InChiKey: AFXZAAMQOFFEBB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanol 在 正丁基锂 、 草酰氯 、 氢氟酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle

  摘要：

  The new simplified dynemicin analogue 16 was prepared enantio- and diastereoselectively in 17 steps starting from monoacetate (S) 7. It is equipped with a side arm containing a protected primary alcoholic function ('handle'), which can be used for conjugation with DNA-complexing agents or for devising new types of trigger. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.029
• 作为产物：
  描述：

  (S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanenitrile 在 二异丁基氢化铝 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以62%的产率得到(S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanol
  参考文献：
  名称：

  Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle

  摘要：

  The new simplified dynemicin analogue 16 was prepared enantio- and diastereoselectively in 17 steps starting from monoacetate (S) 7. It is equipped with a side arm containing a protected primary alcoholic function ('handle'), which can be used for conjugation with DNA-complexing agents or for devising new types of trigger. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.029

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。
• Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle
  作者：Luca Banfi、Andrea Basso、Valentina Gandolfo、Giuseppe Guanti、Renata Riva

  DOI：10.1016/j.tetlet.2004.04.029

  日期：2004.5

  The new simplified dynemicin analogue 16 was prepared enantio- and diastereoselectively in 17 steps starting from monoacetate (S) 7. It is equipped with a side arm containing a protected primary alcoholic function ('handle'), which can be used for conjugation with DNA-complexing agents or for devising new types of trigger. (C) 2004 Elsevier Ltd. All rights reserved.