1-azido-1-methoxydecane | 111238-40-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-1-methoxydecane
• CAS: 111238-40-5
• 化学式: C₁₁H₂₃N₃O
• 分子量: 213.323
• InChiKey: ZQFFKBJZZQITJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-1-methoxydecane 、 乙醇 、 迭氮酸 、 二氯甲烷 、 四氯化钛 以6%的产率得到
  参考文献：
  名称：

  HASSNER, ALFRED;FIBIGER, RICHARD;AMARASEKARA, ANANDA S., J. ORG. CHEM., 53,(1988) N 1, 22-27

  摘要：

  DOI：
• 作为产物：
  描述：

  1,1-二甲氧基癸烷 在 2,4,6-三甲基吡啶 、 三乙基硅基三氟甲磺酸酯 、 sodium azide 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到1-azido-1-methoxydecane
  参考文献：
  名称：

  Organic Chemistry Using Weakly Electrophilic Salts:  Efficient Formation of O,O-Mixed, O,S- and N,O-Acetals

  摘要：

  A mild and efficient method for the preparation of O,O-mixed, O,S- and N,O-acetals from symmetrical O,O-acetals has been developed. Thus, the treatment of symmetrical O,O-acetals with TESOTf and 2,4,6-collidine formed weakly electrophilic collidinium salts. The addition of nucleophiles, such as an alcohol, lithium thioxide, and sodium azide, to the salts afforded the corresponding O,O-mixed, O,S- and N,O-acetals in good yields. The reaction proceeded under weakly basic conditions. No overreaction then occurred and many acid-labile functional groups could remain intact.

  DOI：

  10.1021/jo071187g

文献信息

• Synthetic methods. 25. Titanium tetrachloride-catalyzed addition of hydrazoic acid to aldehydes and ketones. Thermolysis and photolysis of .alpha.-azido ethers
  作者：Alfred Hassner、Richard Fibiger、Ananda S. Amarasekara

  DOI：10.1021/jo00236a006

  日期：1988.1
• HASSNER, ALFRED;FIBIGER, RICHARD;AMARASEKARA, ANANDA S., J. ORG. CHEM., 53,(1988) N 1, 22-27
  作者：HASSNER, ALFRED、FIBIGER, RICHARD、AMARASEKARA, ANANDA S.

  DOI：——

  日期：——
• Organic Chemistry Using Weakly Electrophilic Salts:  Efficient Formation of <i>O</i>,<i>O</i>-Mixed, <i>O</i>,<i>S</i>- and <i>N</i>,<i>O</i>-Acetals
  作者：Hiromichi Fujioka、Takashi Okitsu、Takuya Ohnaka、Ruichuan Li、Ozora Kubo、Kazuhisa Okamoto、Yoshinari Sawama、Yasuyuki Kita

  DOI：10.1021/jo071187g

  日期：2007.10.1

  A mild and efficient method for the preparation of O,O-mixed, O,S- and N,O-acetals from symmetrical O,O-acetals has been developed. Thus, the treatment of symmetrical O,O-acetals with TESOTf and 2,4,6-collidine formed weakly electrophilic collidinium salts. The addition of nucleophiles, such as an alcohol, lithium thioxide, and sodium azide, to the salts afforded the corresponding O,O-mixed, O,S- and N,O-acetals in good yields. The reaction proceeded under weakly basic conditions. No overreaction then occurred and many acid-labile functional groups could remain intact.