(Z)-4,8-dimethylnona-3,7-dienenitrile | 74582-94-8

• 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: (Z)-4,8-dimethylnona-3,7-dienenitrile
• 英文别名: neryl cyanide；Geranylcyanid；(3Z)-4,8-dimethylnona-3,7-dienenitrile
• CAS: 74582-94-8
• 化学式: C₁₁H₁₇N
• 分子量: 163.263
• InChiKey: FRTXHDQZMMZCOJ-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-4,8-dimethylnona-3,7-dienenitrile 、 三甲基硅烷化重氮甲烷 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.3h， 以75%的产率得到4-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-5-trimethylsilanyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  Aoyama, Toyohiko; Sudo, Kimio; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 10, p. 3849 - 3851

  摘要：

  DOI：
• 作为产物：
  描述：

  Phosphoric acid, (2Z)-1-cyano-3,7-dimethyl-2,6-octadien-1-yl diethyl ester 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-4,8-dimethylnona-3,7-dienenitrile
  参考文献：
  名称：

  Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles

  摘要：

  Cyanohydrin diethyl phosphates, readily obtained from various ketones and aldehydes by reaction with diethyl phosphorocyanidate and lithium cyanide, reacted chemoselectively with samarium(II) iodide in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to alpha,beta-unsaturated carbonyl compounds via cyano phosphates to give beta,gamma-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds.

  DOI：

  10.1021/jo00005a031

文献信息

• Reaction of Allyl Diphenyl Phosphates with Soft Bases
  作者：Shuki Araki、Kazuhiro Minami、Yasuo Butsugan

  DOI：10.1246/bcsj.54.629

  日期：1981.2

  The title phosphates were found to react with a variety of soft bases to give nucleophilic substitution products in high yields. The reaction proceeded regiospecifically under mild reaction conditions with preservation of the double bond geometry.

  磷酸酯与多种软碱发生反应，生成高产率的亲核取代产物。该反应在温和的反应条件下进行，具有区域选择性，并保持双键几何形状。
• New Methods and Reagents in Organic Synthesis; 6¹. A Simple One-Pot Conversion of Primary Alcohols to Nitriles having One C-Atom more
  作者：Akira Mizuno、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1055/s-1980-29300

  日期：——
• Cyanation of allylic carbonates and acetates using trimethylsilyl cyanide catalyzed by palladium complex
  作者：Yasushi Tsuji、Naoaki Yamada、Shinsuke Tanaka

  DOI：10.1021/jo00053a007

  日期：1993.1

  Allylic carbonates and acetates are cyanated with trimethylsilyl cyanide in the presence of a catalytic amount (5 mol % based on the allylic substrates) of Pd(PPh3)4 or Pd(CO)(PPh3)3 in THF under reflux to afford beta,gamma-unsaturated nitriles in high yields.
• YONEDA, RYUJI;HARUSAWA, SHINYA;KURIHARA, TAKUSHI, J. ORG. CHEM., 56,(1991) N, C. 1827-1832
  作者：YONEDA, RYUJI、HARUSAWA, SHINYA、KURIHARA, TAKUSHI

  DOI：——

  日期：——
• MIZUNO AKIRA; HAMADA YASUMASA; SHIOIRI TAKAYUKI, SYNTHESIS, 1980, NO 12, 1007-1009
  作者：MIZUNO AKIRA、 HAMADA YASUMASA、 SHIOIRI TAKAYUKI

  DOI：——

  日期：——