Triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium | 690949-10-1

• 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: Triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium
• 英文别名: 5-(Oxan-2-yloxy)pentyl-triphenylphosphanium
• CAS: 690949-10-1
• 化学式: C₂₈H₃₄O₂P
• 分子量: 433.551
• InChiKey: CGXVFXSPYJUNDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium 在 盐酸 、 potassium hexamethyldisilazane 、 水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (Z)-8-Pyridin-3-yloct-5-en-1-ol
  参考文献：
  名称：

  Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis

  摘要：

  The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels-Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH4 . This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis.

  DOI：

  10.1002/(sici)1521-3773(19981016)37:19<2661::aid-anie2661>3.0.co;2-d
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 5-Hydroxypentyltriphenylphosphonium 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以93%的产率得到Triphenyl-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phosphonium
  参考文献：
  名称：

  Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis

  摘要：

  The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels-Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH4 . This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis.

  DOI：

  10.1002/(sici)1521-3773(19981016)37:19<2661::aid-anie2661>3.0.co;2-d

文献信息

• Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis
  作者：Jack E. Baldwin、Timothy D. W. Claridge、Andrew J. Culshaw、Florian A. Heupel、Victor Lee、David R. Spring、Roger C. Whitehead、Robert J. Boughtflower、Ian M. Mutton、Richard J. Upton

  DOI：10.1002/(sici)1521-3773(19981016)37:19<2661::aid-anie2661>3.0.co;2-d

  日期：1998.10.16

  The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels-Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH4 . This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis.