(3R,4R)-3-phenylmethoxyhexadec-1-en-4-ol | 1160163-77-8

• 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: (3R,4R)-3-phenylmethoxyhexadec-1-en-4-ol
• CAS: 1160163-77-8
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: BHJOPMQYRZMMFC-DHIUTWEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-phenylmethoxyhexadec-1-en-4-ol 、 溴乙酸 在 sodium hydride 、 硫酸 作用下， 以 四氢呋喃 、 mineral oil 、 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 0.5h， 以88%的产率得到2-(((3R,4R)-3-(benzyloxy)hexadec-1-en-4-yl)oxy)acetic acid
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w
• 作为产物：
  描述：

  (((3R,4R)-3-(benzyloxy)hexadec-1-en-4-yl)oxy)triethylsilane 在 氢氟酸 、 水 作用下， 以 乙腈 为溶剂， 以100%的产率得到(3R,4R)-3-phenylmethoxyhexadec-1-en-4-ol
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w

文献信息

• Asymmetric Total Synthesis of Pyranicin
  作者：Michael T. Crimmins、Danielle L. Jacobs

  DOI：10.1021/ol900814w

  日期：2009.6.18

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.