8-(2-hexyl-1,3-dioxolan-2-yl)octane-1,2-diol | 884330-53-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-(2-hexyl-1,3-dioxolan-2-yl)octane-1,2-diol
• CAS: 884330-53-4
• 化学式: C₁₇H₃₄O₄
• 分子量: 302.455
• InChiKey: ATXQEBVHUHSWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  21.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  8-(2-hexyl-1,3-dioxolan-2-yl)octane-1,2-diol 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以99%的产率得到7-(2-hexyl-1,3-dioxolan-2-yl)heptanal
  参考文献：
  名称：

  An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins

  摘要：

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.

  DOI：

  10.1021/jo052408q
• 作为产物：
  描述：

  pentadec-1-en-9-one 在 potassium osmate(VI) 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 33.75h， 生成 8-(2-hexyl-1,3-dioxolan-2-yl)octane-1,2-diol
  参考文献：
  名称：

  An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins

  摘要：

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.

  DOI：

  10.1021/jo052408q