(2Z,4E,8E,12E)-14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenal | 130675-21-7

• 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,8E,12E)-14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenal
• 英文别名: (2Z,4E,8E,12E)-14-chloro-5,9,13-trimethyl-2-(1-methylethyl)tetradeca-2,4,8,12-tetraenal；(2Z,4E,8E,12E)-14-chloro-5,9,13-trimethyl-2-propan-2-yltetradeca-2,4,8,12-tetraenal
• CAS: 130675-21-7
• 化学式: C₂₀H₃₁ClO
• 分子量: 322.919
• InChiKey: HKBRZDHGAPVVEV-UIHRRHQOSA-N

物化性质

• 沸点：
  445.6±45.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z,4E,8E,12E)-14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenal 在 potassium cyanide 、 18-冠醚-6 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2Z,4E,8E,12E)-2-(1-Methylethyl)-5,9,13-trimethyl-1-<(trimethylsilyl)oxy>-2,4,8,12-cyclotetradecatetraene-1-carbonitrile
  参考文献：
  名称：

  Stereo- and enantioselective total synthesis of sarcophytol-A

  摘要：

  DOI：

  10.1016/s0040-4039(00)89053-x
• 作为产物：
  描述：

  2-(二乙氧基次膦酰基)-3-甲基丁酸乙酯 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 正丁基锂 、 selenium(IV) oxide 、 二异丁基氢化铝 、 水杨酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 (2Z,4E,8E,12E)-14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenal
  参考文献：
  名称：

  Total Synthesis of Sarcophytol A, an Anticarcinogenic Marine Cembranoid

  摘要：

  A highly stereo- and enantioselective total synthesis of sarcophytol A (1), a marine cembranoid promising as a cancer chemopreventive agent, is described. The nitrile 10 obtained Z-selectively (Z:E = >35:1) by the Horner-Emmons reaction of (E,E)-farnesal (5) with the phosphononitrile 9 in 91% yield was converted to the conjugated 2(Z),4(E)-dienal 3 in which the terminal (E)-methyl group was functionalized. Intramolecular alkylation of the cyanohydrin TMS ether of 3 provided the macrocyclic ketone 2 in 79% of overall yield from 3 without isolation of the cyclic cyanohydrin 20 as well as its TMS ether 19. Reduction of 2 with several chiral LiAlH4 reagents afforded 1 highly enantioselectively (87-93% ee) in 78-97% yield, from which enantiomerically pure 1 (>99% ee) was readily obtained upon a single recrystallization.

  DOI：

  10.1021/jo00089a011

文献信息

• 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：——
• Stereo- and enantioselective total synthesis of sarcophytol-A
  作者：Hisao Takayanagi、Yasunori Kitano、Yasuhiro Morinaka

  DOI：10.1016/s0040-4039(00)89053-x

  日期：1990.1
• Total Synthesis of Sarcophytol A, an Anticarcinogenic Marine Cembranoid
  作者：Hisao Takayanagi、Yasunori Kitano、Yasuhiro Morinaka

  DOI：10.1021/jo00089a011

  日期：1994.5

  A highly stereo- and enantioselective total synthesis of sarcophytol A (1), a marine cembranoid promising as a cancer chemopreventive agent, is described. The nitrile 10 obtained Z-selectively (Z:E = >35:1) by the Horner-Emmons reaction of (E,E)-farnesal (5) with the phosphononitrile 9 in 91% yield was converted to the conjugated 2(Z),4(E)-dienal 3 in which the terminal (E)-methyl group was functionalized. Intramolecular alkylation of the cyanohydrin TMS ether of 3 provided the macrocyclic ketone 2 in 79% of overall yield from 3 without isolation of the cyclic cyanohydrin 20 as well as its TMS ether 19. Reduction of 2 with several chiral LiAlH4 reagents afforded 1 highly enantioselectively (87-93% ee) in 78-97% yield, from which enantiomerically pure 1 (>99% ee) was readily obtained upon a single recrystallization.