(4S,6S,8R,10R,12R)-4,6,8,10,12-pentamethoxy-1-heptadecene | 127999-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6S,8R,10R,12R)-4,6,8,10,12-pentamethoxy-1-heptadecene
• 英文别名: (4S,6S,8S,10R,12R)-4,6,8,10,12-pentamethoxy-1-heptadecene；(4S,6S,8R,10R,12R)-4,6,8,10,12-pentamethoxyheptadec-1-ene
• CAS: 127999-45-5
• 化学式: C₂₂H₄₄O₅
• 分子量: 388.588
• InChiKey: XPAYTAWZHRFGBD-PPGORRQASA-N

物化性质

• 沸点：
  430.2±45.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4S,6S,8R,10R,12R)-4,6,8-trimethoxy-1-heptadecene-10,12-diol 、 碘甲烷 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到(4S,6S,8R,10R,12R)-4,6,8,10,12-pentamethoxy-1-heptadecene
  参考文献：
  名称：

  Isotactic polymethoxy 1-alkenes from blue-green algae. Synthesis and absolute stereochemistry

  摘要：

  Novel isotactic polymethoxy-1-alkenes 1-4 were isolated from tolytoxin-producing blue-green algae belonging to the family Scytonemataceae. Scytonema mirabile produced 1 and 2, whereas 3 and 4 were isolated from S. burmanicum. The gross structures and relative stereochemistries were determined by mass and NMR spectral analyses. The absolute configurations of 1-4 were established by direct comparison with optically active synthetic samples.

  DOI：

  10.1021/jo00002a027

文献信息

• A Butyrolactone → 1,3-diol Strategy for the Obtention ofTolypothrix Polyethers – Total Synthesis of theTolypothrix Pentaether from Enantiomerically EnrichedS-Glycidol
  作者：Henning Priepke、Reinhard Brückner

  DOI：10.1002/jlac.199719970805

  日期：1997.8

  Permethyl ether 1 from Tolypothrix conglutinata was synthesized following the retrosynthetic analysis of Scheme 1. According to it, we combined aldehyde 3 [prepared from S-glycidol (7); cf. Schemes 2, 3] and lactone 4 (also prepared from S-glycidol (7); cf. the preceding communication[2] and Scheme 4) to the enantiopure and diastereopure trimethoxy lactone 2 (Scheme 5). The CO group of this lactone

  的Permethyl醚1从Tolypothrix conglutinata合成根据它，我们结合醛方案1的逆合成分析以下3 [制备自小号-缩水甘油（7）; cf. 方案2、3]和内酯4（也由S-缩水甘油（7）制备；参见前述说明[2]和方案4）对映体和非对映体三甲氧基内酯2（方案5）。该内酯的CO基团通过衍生出的过氧乳糖醇内酯的Criegee重排而被除去（方案6）。因此，内酯2的CCO键被完全保留的构型替换为所得的顺构型二醇18的一个COH键。保护基操作（方案6、7）以及将生成的醇21氧化为醛31（方案10）引发了三个最终操作：用Ph 3 PCH-CHO进行C 2同源（烯醛32），甲苯磺酰的形成（34） ，以及减少/伴随的CC键迁移。他们导致目标醚1与富含CHCH的醚36形成89:11混合物。
• Total Synthesis of theTolypothrix Pentaether from Enantiomerically Pure Homoallyl Alcohols by A Butyrolactone → 1,3-Diol Strategy
  作者：Stefan Weigand、Reinhard Brückner

  DOI：10.1002/jlac.199719970806

  日期：1997.8

  Scheme 1 the permethyl ether 1 from Tolypothrix conglutinata was synthesized from aldehyde 2 and the hydroxylated butyrolactone 3b. Each of these building blocks was obtained from a homoallyl alcohol, i. e. aldehyde 2 from homoallyl alcohol 5 (Scheme 3; 98.1% ee) and lactone 3b from homoallyl alcohol 30 (Schemes 10, 11; 97.7% ee). These alcohols, in turn, stemmed from the Ti(OEt)4/S-BINOL-mediated enantioselective

  以下方案1中的全甲基醚的逆合成计划1从Tolypothrix conglutinata从醛合成2和羟基化丁内酯3b中。这些结构单元中的每一个均得自均烯丙基醇，即得自均烯丙基醇5的醛2（方案3； 98.1％ee）和得自均烯丙基醇30的内酯3b（方案10、11； 97.7％ee）。这些醇又源于Ti（OEt）4 / S -BINOL介导的β-取代的锡烷7的对映选择性加成。己醛（方案3）和Ti（OEt）4 / R -BINOL介导的将β-取代的锡烷31对映选择性加成到醛32上（方案10）。羟基内酯3b进行O-甲基化后（方案11），通过对Peterson烯化反应进行Larson修饰，将所得的甲氧基内酯38与醛2缩合，以提供Z / E异构体的65:35混合物形式的γ-亚烷基内酯39（方案12）。将该混合物氢化，得到顺式构型的γ-烷基内酯40（方案12）。伴随有不超过5摩尔％的其反式异构体。该观察似乎暗
• Isotactic polymethoxy 1-alkenes from blue-green algae. Synthesis and absolute stereochemistry
  作者：Yuji Mori、Yasunori Kohchi、Makoto Suzuki、Shmuel Carmeli、Richard E. Moore、Gregory M. L. Patterson

  DOI：10.1021/jo00002a027

  日期：1991.1

  Novel isotactic polymethoxy-1-alkenes 1-4 were isolated from tolytoxin-producing blue-green algae belonging to the family Scytonemataceae. Scytonema mirabile produced 1 and 2, whereas 3 and 4 were isolated from S. burmanicum. The gross structures and relative stereochemistries were determined by mass and NMR spectral analyses. The absolute configurations of 1-4 were established by direct comparison with optically active synthetic samples.