4-azido-4-(4-chlorophenyl)butan-1-ol | 1462249-03-1

• 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: 4-azido-4-(4-chlorophenyl)butan-1-ol
• 英文别名: 4-Azido-4-(4-chlorophenyl)butan-1-ol
• CAS: 1462249-03-1
• 化学式: C₁₀H₁₂ClN₃O
• 分子量: 225.678
• InChiKey: HDZIWDMEVIROCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-chlorophenyl)tetrahydrofuran 在 iron(III) chloride 、 叠氮基三甲基硅烷 、 四丁基氟化铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到4-azido-4-(4-chlorophenyl)butan-1-ol
  参考文献：
  名称：

  Iron-Catalyzed Ring-Opening Azidation and Allylation of O-Heterocycles

  摘要：

  We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron bichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.

  DOI：

  10.1021/ol402511r

文献信息

• Dual Photoredox/Copper Catalysis for the Remote C(sp³ )−H Functionalization of Alcohols and Alkyl Halides by <i>N</i> -Alkoxypyridinium Salts
  作者：Xu Bao、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.201813356

  日期：2019.2.11

  Under mild dual photoredox/copper catalysis, the reaction of N‐alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded δ‐azido, δ‐cyano, and δ‐thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5‐hydrogen atom transfer (1,5‐HAT) and copper‐catalyzed functionalization of the resulting C‐centered

  在温和的双重光氧化还原/铜催化下，N-烷氧基吡啶鎓盐与易于获得的甲硅烷基试剂（TMSN 3，TMCSN，TMSNCS）的反应可高产率提供δ-叠氮基，δ-氰基和δ-硫氰基醇。该反应经历了一个多米诺骨牌过程，该过程涉及烷氧基自由基的产生，1,5-氢原子转移（1,5-HAT）以及铜催化的C中心自由基的官能化。还记录了催化对映选择性δ-C（sp 3）-H氰化的条件。
• Iron-Catalyzed Ring-Opening Azidation and Allylation of <i>O</i>-Heterocycles
  作者：Yoshinari Sawama、Kyoshiro Shibata、Yuka Sawama、Masato Takubo、Yasunari Monguchi、Norbert Krause、Hironao Sajiki

  DOI：10.1021/ol402511r

  日期：2013.10.18

  We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron bichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.