Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide | 88730-62-5

• 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: Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide
• CAS: 88730-62-5
• 化学式: C₂₉H₃₄O₂P*I
• 分子量: 572.466
• InChiKey: SMDLUQYQIQSJDN-ODZAUARKSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (3Z,6Z)-Heptadeca-3,6-dien-1-ol
  参考文献：
  名称：

  Asymmetric hydroxylation with lipoxygenase: the role of group hydrophobicity on regioselectivity

  摘要：

  Changes in the regioselectivity for the lipoxygenase 1 catalyzed oxidation of the unnatural substrates 5a-f [(Z,-Z)-HOOC(CH2)4C( = O)O(CH = CHCH2CH = CHR; R, a-f = n-C5H11-n-C10H21[ to afford regioisomeric diols 3 ](Z,E)-HOCH2CH2CH = CHCH = CHCH(OH)R[ and 4 ](E,Z)-HOCH2CH2CH(OH)CH = CH = CHR] as a function of the hydrophobicity of the distal R group were investigated. The results demonstrate that the ratio of products 3/4 decreases steadily as the hydrophobicity of the distal group is increased incrementally from n-C5H11 to n-C10H21. Conversley, changes in the proximal group hydrophobicity by varying the prosthetic modifier for substrates 6a-e {(Z,Z)-HOOC(CH2)xC-(= O)O(CH2)2CH = CHCH2H = CHC8H17; X, a-e = 2-6) gave opposite changes in the regiospecificity of oxidation. For example, increasing the hydrophobicity of the proximal group from X = 4 = 6 led to an increase in the regioselective formation of diol 3. Decreasing the value of X led to preferential formation of diol 4. Hence, the regiochemical outcome of the enzyme-catalyzed reaction appears to be influenced by the hydrophobic differential between the proximal and distal groups. The data suggests that optimization of the regioselectivity for new substrates can be achieved by careful selection of modifier groups used in the design of substrate structure.

  DOI：

  10.1021/ja00001a039
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 60.0h， 生成 Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide
  参考文献：
  名称：

  Synthesis of .omega.-tritiated and .omega.-fluorinated analogs of the trail pheromone of subterranean termites

  摘要：

  DOI：

  10.1021/jo00181a023

文献信息

• Syntheses and NMR analyses of the eight geometric isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trail pheromone
  作者：Bryan K. Eya、Otsuka Toshikazu、Kubo Isao、David L. Wood

  DOI：10.1016/s0040-4020(01)88364-2

  日期：1990.1

  via a Wittig olefination reaction. The conver-gent syntheses of 1 consisted of a combination of two fragments, each containing an olefin with a fixed configuration, by formation of a third double bond to give a mixture of two geometric isomers. The mixtures of 1 were resolved by recycle high-performance liquid chromatography methods. 1H and 13C NMR peak assignments of the individual isomers were accomplished

  通过Wittig烯化反应合成了3,6,8-十二碳三烯-1-醇1的八个几何异构体，即地下白蚁的尾随信息素（sp。Banks ）。1的收敛合成由两个片段的组合组成，每个片段包含一个具有固定构型的烯烃，这是通过形成第三个双键给出的两种几何异构体的混合物。1的混合物通过循环高效液相色谱法分离。单个异构体的1 H和13 C NMR峰分配通过同核COSY和一键CH相关光谱法完成。
• Morikawa, Tsutomu; Nishiwaki, Tohru; Nakamura, Keiichi, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 3, p. 813 - 815
  作者：Morikawa, Tsutomu、Nishiwaki, Tohru、Nakamura, Keiichi、Kobayashi, Yoshiro

  DOI：——

  日期：——