4-氨基-2-甲基-3-己醇 | 63765-80-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-氨基-2-甲基-3-己醇
• 英文名称: 4-Amino-2-methyl-hexan-3-ol
• 英文别名: 3-Hexanol, 4-amino-2-methyl-；4-amino-2-methylhexan-3-ol
• CAS: 63765-80-0
• 化学式: C₇H₁₇NO
• 分子量: 131.218
• InChiKey: KHRLRJPSKWLLPI-UHFFFAOYSA-N

物化性质

• 熔点：
  -12.63°C (estimate)
• 沸点：
  242.56°C (rough estimate)
• 密度：
  0.8662 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

制备方法与用途

类别：有毒物品
毒性分级：高毒
急性毒性：腹腔-小鼠LD50：25毫克/公斤
可燃性危险特性：可燃；燃烧产生有毒氮氧化物烟雾
储运特性：库房通风、低温干燥
灭火剂：干粉、泡沫、砂土、二氧化碳，雾状水

反应信息

• 作为反应物：
  描述：

  氯甲酸苄酯 、 4-氨基-2-甲基-3-己醇 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 anti-4-<(Benzyloxycarbonyl)amino>-2-methyl-3-hexanol 、 syn-4-<(Benzyloxycarbonyl)amino>-2-methyl-3-hexanol
  参考文献：
  名称：

  Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

  摘要：

  Preparation of an isocyanide having a removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide was prepared from commercially available 3,5-xylenol. The isocyanide underwent a samarium iodide-mediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-(arylamino) alcohols, which were then deprotected to the corresponding 2-(primary amino) alcohols via desilylation with TBAF followed by oxidation with DDQ. A ceramide was successfully synthesized by use of the present stereoselective synthetic method for 2-amino alcohols, demonstrating a new synthetic utility of the isocyanide as an aminomethylene equivalent.

  DOI：

  10.1021/jo00076a042
• 作为产物：
  描述：

  4-<<4-(tert-Butyldimethylsiloxy)-2,6-xylyl>amino>-2-methyl-3-hexanol 在 盐酸 、 四丁基氟化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 4-氨基-2-甲基-3-己醇
  参考文献：
  名称：

  Stereoselective synthesis of 2-amino alcohols by use of an isocyanide as an aminomethylene equivalent

  摘要：

  Preparation of an isocyanide having a removable N-substituent and its application to the stereoselective synthesis of 2-amino alcohols are described. 4-(tert-Butyldimethylsiloxy)-2,6-xylyl isocyanide was prepared from commercially available 3,5-xylenol. The isocyanide underwent a samarium iodide-mediated coupling reaction with organic halides and carbonyl compounds. Reduction of the reaction mixture with NaBH4 selectively afforded anti 2-(arylamino) alcohols, which were then deprotected to the corresponding 2-(primary amino) alcohols via desilylation with TBAF followed by oxidation with DDQ. A ceramide was successfully synthesized by use of the present stereoselective synthetic method for 2-amino alcohols, demonstrating a new synthetic utility of the isocyanide as an aminomethylene equivalent.

  DOI：

  10.1021/jo00076a042

文献信息

• SEEBACH D.; BECK A. K.; LEHR F.; WELLER T.; COLVIN E. W., ANGEW. CHEM., 1981, 93, NO 4, 422-424
  作者：SEEBACH D.、 BECK A. K.、 LEHR F.、 WELLER T.、 COLVIN E. W.

  DOI：——

  日期：——