(2Z,4E)-8-hydroxy-5,9-dimethyl-2-(1-methylethyl)deca-2,4,9-trienenitrile | 147458-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2Z,4E)-8-hydroxy-5,9-dimethyl-2-(1-methylethyl)deca-2,4,9-trienenitrile
• 英文别名: (2Z,4E)-8-hydroxy-5,9-dimethyl-2-propan-2-yldeca-2,4,9-trienenitrile
• CAS: 147458-69-3
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: OMPMXURVOLKFDL-HKAZRAOBSA-N

物化性质

• 沸点：
  383.2±42.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-8-hydroxy-5,9-dimethyl-2-(1-methylethyl)deca-2,4,9-trienenitrile 在 2,4-二硝基酚 、 葡萄糖 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (2Z,4E,8E,12R)-12,13-dihydroxy-5,9,13-trimethyl-2-propan-2-yltetradeca-2,4,8-trienenitrile
  参考文献：
  名称：

  Total syntheses of both enantiomers of sarcophytols A and T based on stereospecific [2,3]Wittig rearrangement

  摘要：

  Both enantiomers of sarcophytols A (1) and T (2), cembranolide diterpenes isolated from a soft coral, were synthesized from a common chiral intermediate, obtained by baker's yeast reduction, using a stereospecific [2,3]Wittig rearrangement as the key step.

  DOI：

  10.1016/s0040-4039(00)61357-6
• 作为产物：
  描述：

  (E)-3,7-二甲基-2,6-辛二烯醛 在 aluminum isopropoxide 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 生成 (2Z,4E)-8-hydroxy-5,9-dimethyl-2-(1-methylethyl)deca-2,4,9-trienenitrile
  参考文献：
  名称：

  Total syntheses of both enantiomers of sarcophytols A and T based on stereospecific [2,3]Wittig rearrangement

  摘要：

  Both enantiomers of sarcophytols A (1) and T (2), cembranolide diterpenes isolated from a soft coral, were synthesized from a common chiral intermediate, obtained by baker's yeast reduction, using a stereospecific [2,3]Wittig rearrangement as the key step.

  DOI：

  10.1016/s0040-4039(00)61357-6

文献信息

• Highly Stereoselective Synthesis of Trisubstituted<i>γ</i>,<i>δ</i>-Unsaturated Acid and Aldehyde<i>via</i>Ketal Claisen Rearrangement
  作者：Hisao Takayanagi、Yasuhiro Morinaka

  DOI：10.1246/cl.1995.565

  日期：1995.7

  A new sequence for the highly stereoselective (E>99%) synthesis of a trisubstituted γ,δ-unsaturated acid (3), which consists of a ketal Claisen rearrangement of a terpene allylic alcohol with 2,2-dimethoxy-3-methyl-3-butanol and a subsequent oxidative cleavage of the resulting α-ketol, is applicable even to the preparation of 3 which is difficult to synthesize by traditional methods. The related procedure

  三取代 γ,δ-不饱和酸 (3) 的高立体选择性 (E>99%) 合成新序列，该序列由萜烯烯丙醇与 2,2-二甲氧基-3-甲基-的缩酮克莱森重排组成3-丁醇和随后产生的α-酮醇的氧化裂解甚至适用于传统方法难以合成的3的制备。还描述了制备相应醛的相关程序。
• Takayanagi, Hisao; Sugiyama, Shigeo; Morinaka, Yasuhiro, Journal of the Chemical Society. Perkin transactions I, 1995, # 7, p. 751 - 756
  作者：Takayanagi, Hisao、Sugiyama, Shigeo、Morinaka, Yasuhiro

  DOI：——

  日期：——
• Total syntheses of both enantiomers of sarcophytols A and T based on stereospecific [2,3]Wittig rearrangement
  作者：Mitsuaki Kodama、Suzuyo Yoshio、Shinji Yamaguchi、Yoshiyasu Fukuyama、Hisao Takayanagi、Yasuhiro Morinaka、Shuji Usui、Yoshimasa Fukazawa

  DOI：10.1016/s0040-4039(00)61357-6

  日期：1993.1

  Both enantiomers of sarcophytols A (1) and T (2), cembranolide diterpenes isolated from a soft coral, were synthesized from a common chiral intermediate, obtained by baker's yeast reduction, using a stereospecific [2,3]Wittig rearrangement as the key step.