<5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide | 79734-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide
• 英文别名: ((2E,4E)-5-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dien-1-yl)triphenylphosphonium bromide；(4R,2ZE,4Z)-[5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide；[5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide；[5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl]triphenylphosphonium bromide；[(2E,4E)-5-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3-methylpenta-2,4-dienyl]-triphenylphosphanium;bromide
• CAS: 79734-41-1
• 化学式: Br*C₃₃H₃₈OP
• 分子量: 561.542
• InChiKey: VRQWQXGLQRBPOW-UHYZDGIKSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide 在 1,2-环氧丁烷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 7.33h， 生成 3-hydroxy-β-apo-10'-carotenoic acid
  参考文献：
  名称：

  Synthesis and Characterization of Quantum Dot Nanoparticles Bound to the Plant Volatile Precursor of Hydroxy-apo-10′-carotenal

  摘要：

  This study is focused on the synthesis and characterization of hydroxy-apo-10'-carotenal/quantum dot (QD) conjugates aiming at the in vivo visualization of β-ionone, a carotenoid-derived volatile compound known for its important contribution to the flavor and aroma of many fruits, vegetables, and plants. The synthesis of nanoparticles bound to plant volatile precursors was achieved via coupling reaction of the QD to C27-aldehyde which was prepared from α-ionone via 12 steps in 2.4% overall yield. The formation of the QD-conjugate was confirmed by measuring its fluorescence spectrum to observe the occurrence of fluorescence resonance energy transfer.

  DOI：

  10.1021/jo500605c
• 作为产物：
  描述：

  (E)-4-((1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-but-3-en-2-one 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 3.5h， 生成 <5-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide
  参考文献：
  名称：

  Synthesis and Characterization of Quantum Dot Nanoparticles Bound to the Plant Volatile Precursor of Hydroxy-apo-10′-carotenal

  摘要：

  This study is focused on the synthesis and characterization of hydroxy-apo-10'-carotenal/quantum dot (QD) conjugates aiming at the in vivo visualization of β-ionone, a carotenoid-derived volatile compound known for its important contribution to the flavor and aroma of many fruits, vegetables, and plants. The synthesis of nanoparticles bound to plant volatile precursors was achieved via coupling reaction of the QD to C27-aldehyde which was prepared from α-ionone via 12 steps in 2.4% overall yield. The formation of the QD-conjugate was confirmed by measuring its fluorescence spectrum to observe the occurrence of fluorescence resonance energy transfer.

  DOI：

  10.1021/jo500605c

文献信息

• Carotenoids and Related Compounds. Part 36.. Further syntheses of zeaxanthin and rhodoxanthin
  作者：Peter R. Ellis、A. Erol Faruk、Gerard P. Moss、Basil C. L. Weedon

  DOI：10.1002/hlca.19810640414

  日期：1981.6.10

  A modification of a previously reported synthesis of zeaxanthin (1), and routes to both zeaxanthin and rhodoxanthin (2) from α-ionone, are described.

  描述了对先前报道的玉米黄质（1）合成方法的修改，以及从α-紫罗兰酮制得玉米黄质和rhodoxanthin（2）的途径。
• Catalytic hydrogenation
  申请人：Hoffmann-La Roche Inc.

  公开号：US04544770A1

  公开（公告）日：1985-10-01

  Compounds of the formula: ##STR1## wherein R.sup.1 is a 2,6,6-trimethyl-1-cyclohexen-1-yl or 2,3,6-trimethylphenyl group, either of which may be unsubstituted or substituted by a hydroxy group or a protected hydroxy group, R.sup.2 is aryl, and X.sup.- is an anion are manufactured by hydrogenating a compound of the formula: ##STR2## wherein R.sup.1, R.sup.2 and X.crclbar. are as above, in an organic solvent or aqueous-organic solvent in the presence of a nickel-, palladium-, platinum-, cobalt-, rhodium-, iridium-, or ruthenium-containing catalyst. The process is suitable as an intermediate step in carotenoid and retinoid syntheses.

  化合物的公式：## STR1 ##其中R.sup.1是2,6,6-三甲基-1-环己烯-1-基或2,3,6-三甲基苯基基团，两者均可为未取代或取代羟基或保护羟基，R.sup.2为芳基，X.sup.-为阴离子，通过在有机溶剂或水-有机溶剂中，在含有镍、钯、铂、钴、铑、铱或钌的催化剂存在下，氢化公式的化合物制造而成：## STR2 ##其中R.sup.1，R.sup.2和X.crclbar.如上所述。该过程适用于类胡萝卜素和视黄醇合成的中间步骤。
• The Longest Polyene
  作者：Muhammad Zeeshan、Hans-Richard Sliwka、Vassilia Partali、Ana Martínez

  DOI：10.1021/ol302577d

  日期：2012.11.2

  A microwave assisted Wittig reaction allowed the synthesis, in good yields, of the longest polyene so far recorded with 27 conjugated double bonds. The synthesis of this stable, well-soluble polyene represents a noteworthy step in the direction of ultimate lambda(max).