(2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate | 122445-36-7

• 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: (2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate
• 英文别名: [(2S,3R)-2-hydroxy-2-(hydroxymethyl)-3,7-dimethyloct-6-enyl] 2,2-dimethylpropanoate
• CAS: 122445-36-7
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: RXELGBPOSHUARB-CJNGLKHVSA-N

物化性质

• 沸点：
  400.9±45.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 camphor-10-sulfonic acid 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (4S)-4-Carbomethoxy-2,2-dimethyl-4-<(1R)-1,5-dimethyl-4-hexenyl>-1,3-dioxolane
  参考文献：
  名称：

  Stereoselective synthesis of the pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

  摘要：

  Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described. The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30. The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol. A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-beta-citronellol (36). This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid. A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2). This acid was coupled to the retronecine borane 82 and then lactonized to 2.

  DOI：

  10.1021/jo00034a017
• 作为产物：
  描述：

  在 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 cerium(III) chloride 、 (-)-diisopropyl tartrate 、 过氧化氢异丙苯 、 MS 3 Angstroem 、 碳酸氢钠 、 碘甲烷 作用下， 以 甲醇 、 苯 为溶剂， 反应 35.83h， 生成 (2S,3R)-3,7-Dimethyl-2-hydroxy-2-(hydroxymethyl)-6-octenyl Pivalate
  参考文献：
  名称：

  Stereoselective synthesis of the pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

  摘要：

  Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described. The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30. The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol. A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-beta-citronellol (36). This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid. A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2). This acid was coupled to the retronecine borane 82 and then lactonized to 2.

  DOI：

  10.1021/jo00034a017

文献信息

• Synthesis of the macrolactone alkaloid (+)-usaramine via necic acid coupling to a pyrrolizidine borane
  作者：James D. White、John C. Amedio、Samuel Gut、Lalith Jayasinghe

  DOI：10.1021/jo00279a005

  日期：1989.9
• WHITE, JAMES D.;AMEDIO, JOHN C. (JR);GUT, SAMUEL;JAYASINGHE, LALITH, J. ORG. CHEM., 54,(1989) N8, C. 4268-4270
  作者：WHITE, JAMES D.、AMEDIO, JOHN C. (JR)、GUT, SAMUEL、JAYASINGHE, LALITH

  DOI：——

  日期：——