trans(C₁₀)allofarnesene | 26560-15-6

• 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: trans(C₁₀)allofarnesene
• 英文别名: (2Z,4E,6E)-allofarnesene；allofarnesene, Z,E,E-；(2Z,4E,6E)-3,7,11-trimethyl-dodeca-2,4,6,10-tetraene；trans(C10)-Allofamesen；allo-Farnesen；(Z)2,(E)4,(E)6-Allofarnesene；(2Z,4E,6E)-3,7,11-trimethyldodeca-2,4,6,10-tetraene
• CAS: 26560-15-6
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: JEKGHHPMLRLCIW-PTXCUWFCSA-N

物化性质

• 沸点：
  283.4±10.0 °C(Predicted)
• 密度：
  0.817±0.06 g/cm3(Predicted)
• 保留指数：
  1600;1600

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  反式,反式-金合欢醇 在 rhodium(II) chloride potassium hydrogensulfate 作用下， 以 乙醇 为溶剂， 生成 trans(C₁₀)allofarnesene
  参考文献：
  名称：

  Synthesis of trans, trans-.alpha.-farnesene

  摘要：

  DOI：

  10.1021/jo01264a011

文献信息

• Stereospecific Synthesis of (2<i>Z</i>,4<i>E</i>,6<i>E</i>)-3,7,11-Trimethyl-2,4,6,10-dodecatetraene [<i>trans</i>(C₁₀)-Allofarnesene]
  作者：Norio Miyaura、Hiroshi Suginome、Akira Suzuki

  DOI：10.1246/bcsj.55.2221

  日期：1982.7

  The stereospecific synthesis of the title acyclic sesquiterpene, isolated from Perilla frutscens f. viridis Makino (Japanese name, Aojiso) by the palladium-catalyzed cross-coupling of 2-(4,8-dimethyl-1,3,7-nonatrienyl)-1,3,2-benzodioxaborole with (Z)-2-bromo-2-butene, is described. The benzodioxaborole was prepared by the hydroboration of 4,8-dimethyl-3,7-nonadien-1-yne, newly prepared via three steps from geranial, with 1,3,2-benzodioxaborole.

  本文描述了从紫苏（Perilla frutscens f. viridis Makino，日本名Aojiso）中分离出的标题为无环倍半萜的立体选择性合成，该合成是通过钯催化2-(4,8-二甲基-1,3,7-壬三烯基)-1,3,2-苯并二氧硼烷与(Z)-2-溴-2-丁烯的交叉偶联反应实现的。苯并二氧硼烷是通过4,8-二甲基-3,7-壬二烯-1-炔的氢硼化反应制备的，该反应是通过从香叶醛到1,3,2-苯并二氧硼烷的三个步骤新制备的。
• Synthesis and purification of the allofarnesenes
  作者：Howard J. Williams、Michael R. Strand、S.Bradleigh Vinson

  DOI：10.1016/s0040-4020(01)92343-9

  日期：1981.1
• The biosynthetic pathway to abscisic acid via ionylideneethane in the fungus Botrytis cinerea
  作者：Masahiro Inomata、Nobuhiro Hirai、Ryuji Yoshida、Hajime Ohigashi

  DOI：10.1016/j.phytochem.2004.08.025

  日期：2004.10

  The biosynthetic pathway to abscisic acid (ABA) from isopentenyl diphosphate in the fungus, Botrytis cinerea, was investigated. Labeling experiments with O-18(2) and (H2O)-O-18 indicated that all oxygen atoms at C1, -1, -1' and -4' of ABA were derived from molecular oxygen, and not from water. This finding was inconsistent not only with the known carotenoid pathway via oxidative cleavage of carotenoids, but also with the classical direct pathway via cyclization of farnesyl diphosphate. The fungus produced new C-15-compounds, 2E,4E-alpha-ionylideneethane and 2Z,4E-alpha-ionylideneethane, along with 2E,4E,6E-allofarnesene and 2Z,4E,6E-allofarnesene, but did not apparently produce carotenoids except for a trace of phytoene. The C-15-compounds labeled with C-13 were converted to ABA by the fungus, and the incorporation ratio of 2Z,4E-alpha-ionylideneethane was higher than that of 2E,4E-alpha-ionylideneethane. From these results, it was concluded that farnesyl diphosphate was reduced at C-1, desaturated at C-4, and isomerized at C-2 to form 2Z,4E,6E-allofarnesene before being cyclized to 2Z,4E-alpha-ionylideneethane; the ionylideneethane was then oxidized to ABA with molecular oxygen. This direct pathway via ionylideneethane means that the biosynthetic pathway to fungal ABA, not only before but also after isopentenyl diphosphate, differs from that to ABA in plants, since plant ABA is biosynthesized using the non-mevalonate and carotenoid pathways. (C) 2004 Elsevier Ltd. All rights reserved.
• ISHIYAMA TATSUO; MIYAURA NORIO; SUZUKI AKIRA, CHEM. LETT.,(1987) N 1, 25-28
  作者：ISHIYAMA TATSUO、 MIYAURA NORIO、 SUZUKI AKIRA

  DOI：——

  日期：——
• Synthesis of trans, trans-.alpha.-farnesene
  作者：Gottfried Brieger、Terry J. Nestrick、Charles McKenna

  DOI：10.1021/jo01264a011

  日期：1969.12