(E)-6-tert-butylocta-2,7-dienyl acetate | 868248-68-4

• 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: (E)-6-tert-butylocta-2,7-dienyl acetate
• 英文别名: [(2E)-6-tert-butylocta-2,7-dienyl] acetate
• CAS: 868248-68-4
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: DTQZXGYMITZBNT-VQHVLOKHSA-N

物化性质

• 沸点：
  284.5±19.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-tert-butylocta-2,7-dienyl acetate 在 四(三苯基膦)钯 偶氮二异丁腈 、 p-tolyl benzeneselenosulfonate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 1-[(2-tert-butyl-5-vinylcyclopentyl)methanesulfonyl]-4-methylbenzene
  参考文献：
  名称：

  Free-Radical-5-exo-Trig Cyclization of Chiral 3-Silylhepta-1,6-dienes:  Concise Approach to the A−B−C Ring Core of Hexacyclinic Acid

  摘要：

  Free-radical-mediated 5-exo-trig cyclization of hepta-1,6-dienes 6a-c incorporating an allylsilane moiety was shown to provide at low temperature exclusively the trans-cis cyclopentanes 7a-c in good yield. In contrast, the same reaction with the alkyl analogue 9a led to the formation of all four possible stereoisomers. Interestingly, extension of this sequence of radical processes to alkoxy analogues 12-14 provided the complementary cis-cis stereoisomers with modest to excellent stereoselectivity. It is noteworthy that under such conditions allylsilanes were found to be much more reactive than their alkyl and alkoxy analogues. Beckwith-Houk-type models were proposed that rationalize the stereochemical course of these 5-exo-trig cyclizations. Finally, an illustration of the value of this methodology was proposed with the synthesis of the A-B-C tricyclic unit of polyketide hexacyclinic acid 3a.

  DOI：

  10.1021/jo051062g
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-6-tert-butylocta-2,7-dienyl acetate
  参考文献：
  名称：

  Free-Radical-5-exo-Trig Cyclization of Chiral 3-Silylhepta-1,6-dienes:  Concise Approach to the A−B−C Ring Core of Hexacyclinic Acid

  摘要：

  Free-radical-mediated 5-exo-trig cyclization of hepta-1,6-dienes 6a-c incorporating an allylsilane moiety was shown to provide at low temperature exclusively the trans-cis cyclopentanes 7a-c in good yield. In contrast, the same reaction with the alkyl analogue 9a led to the formation of all four possible stereoisomers. Interestingly, extension of this sequence of radical processes to alkoxy analogues 12-14 provided the complementary cis-cis stereoisomers with modest to excellent stereoselectivity. It is noteworthy that under such conditions allylsilanes were found to be much more reactive than their alkyl and alkoxy analogues. Beckwith-Houk-type models were proposed that rationalize the stereochemical course of these 5-exo-trig cyclizations. Finally, an illustration of the value of this methodology was proposed with the synthesis of the A-B-C tricyclic unit of polyketide hexacyclinic acid 3a.

  DOI：

  10.1021/jo051062g