triphenylhept-2-ylphosphonium bromide | 13751-90-1

• 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: triphenylhept-2-ylphosphonium bromide
• 英文别名: Triphenyl-2-heptyl-phosphoniumbromid；Heptan-2-yl(triphenyl)phosphanium;bromide
• CAS: 13751-90-1
• 化学式: Br*C₂₅H₃₀P
• 分子量: 441.391
• InChiKey: OFSOLXIBTOSQKK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  triphenylhept-2-ylphosphonium bromide 、 丙烯醛 在 正丁基锂 作用下， 以 乙醚 为溶剂， 生成 (E)-4-methyl-1,3-nonadiene 、 (Z)-4-methyl-1,3-nonadiene
  参考文献：
  名称：

  Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents

  摘要：

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.

  DOI：

  10.1021/jo00007a055
• 作为产物：
  描述：

  2-溴庚烷 、 三苯基膦 生成 triphenylhept-2-ylphosphonium bromide
  参考文献：
  名称：

  四氢大麻酚类似物。2-（3-甲基-2-辛基）-3-羟基-6,6,9-三甲基-7,8,9,10-四氢二苯并（b，d）吡喃的合成

  摘要：

  由4-乙酰间苯二酚经七个步骤合成了标题化合物，该化合物为先前已知具有有效的“大麻样”活性的化合物（IV）的位置异构体（在酚环中）。令人惊讶地，发现它在生理上是无活性的。探索了一种替代的，潜在的通用的THC结构类似物合成路线，该路线涉及应用羟基四氢二苯并吡喃酮（XVIII）和-pyrans（XX）的酯进行弗里斯重排。

  DOI：

  10.1016/s0040-4020(01)83288-9

文献信息

• Alkylation of allylic derivatives. 17. Cross-coupling reactions of diallylic pivalates with butyl- and phenylcopper reagents
  作者：Ted L. Underiner、Harlan L. Goering

  DOI：10.1021/jo00007a055

  日期：1991.3

  Cross coupling (Z)-1-phenyl-1,4-pentadien-3-yl pivalate (cis-1-OPiv) with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph gives only the fully conjugated gamma-coupling product. With LiCuBu2, substantial loss of double-bond configuration occurs to give primarily the all-trans coupling product. With other cuprates, no detectable loss of double-bond configuration was observed. Cross coupling (Z)-3-(2-phenylethenyl)2-cyclohexen-1-yl pivalate (cis-18-OPiv) with LiCuBu2, LiCuPh2, and LiCu(CN) ph gives only alpha-coupling product; with LiCu(CN)Bu, a mixture of alpha, gamma, and epsilon coupling product was obtained. Cross coupling with LiCuBu2, results in loss of double-bond configuration in the alpha-alkylation product. With the other cuprates, no loss of double-bond configuration was detected in the alpha and gamma coupling product. These results have profound mechanistic implications, which are discussed. The relationship between structure and reactivity was also investigated. A variety of diallylic pivalates (1-5 OPiv) were prepared and cross coupled with LiCuBu2, LiCu(CN)Bu, LiCuPh2, and LiCu(CN)Ph. Generally, coupling occurs at the least-substituted allylic system; mechanistic implications are discussed.
• Tetrahydrocannabinol analogs. Synthesis of 2-(3-methyl-2-octyl)-3-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydrodibenzo(b,d)pyran
  作者：E.C. Taylor、K. Lenard、B. Loev

  DOI：10.1016/s0040-4020(01)83288-9

  日期：1967.1

  phenolic ring) of a compound (IV) previously known to possess potent “marijuana-like” activity, has been synthesized in seven steps from 4-acetylresorcinol; surprisingly, it was found to be physiologically inactive. An alternative, potentially versatile synthetic route to structural analogs of THC was explored which involved application of the Fries rearrangement of esters of hydroxytetrahydrodibenzopyrones

  由4-乙酰间苯二酚经七个步骤合成了标题化合物，该化合物为先前已知具有有效的“大麻样”活性的化合物（IV）的位置异构体（在酚环中）。令人惊讶地，发现它在生理上是无活性的。探索了一种替代的，潜在的通用的THC结构类似物合成路线，该路线涉及应用羟基四氢二苯并吡喃酮（XVIII）和-pyrans（XX）的酯进行弗里斯重排。