(4R,6R)-6-phenylmethoxyhept-1-en-4-ol | 89104-05-2

• 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: (4R,6R)-6-phenylmethoxyhept-1-en-4-ol
• CAS: 89104-05-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: UCBRUQGFKILSTQ-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,6R)-6-phenylmethoxyhept-1-en-4-ol 在 palladium on activated charcoal 、 对甲苯磺酸 氢气 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (2SR,4SR,6RS)-4-Methyl-2-phenyl-6-propyl-1,3-dioxane
  参考文献：
  名称：

  Acyclic stereoselection. 22. Diastereofacial selectivity in the Lewis acid mediated reactions of allylsilanes with chiral aldehydes and enones

  摘要：

  DOI：

  10.1021/jo00196a022
• 作为产物：
  描述：

  (R)-3-苄氧基丁醛 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (4R,6R)-6-phenylmethoxyhept-1-en-4-ol
  参考文献：
  名称：

  A synthesis of (+)-nonactic acid by means of the sulfur-ylide rearrangement

  摘要：

  (+)-Nonactic acid (1) 已通过在乙酸铑的存在下，使四氢-2-糠酸酐 (9) 与二甲基α-叠氮代丙二酸酯发生缩合反应的关键反应而成功合成。

  DOI：

  10.1016/s0040-4020(01)80580-9

文献信息

• The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the CD-spiroacetal segment
  作者：Ian Paterson、Mark J. Coster、David Y.-K. Chen、Karl R. Gibson、Debra J. Wallace

  DOI：10.1039/b504148a

  日期：——

  Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 , relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60 : 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal by acid-promoted equilibration

  依赖于螺缩醛形成的动力学和热力学控制，描述了altohyrtin A /海绵抑素1的C16-C28 CD-螺缩醛亚基的立体控制合成。动力学控制方法导致所希望的螺缩醛异构体稍微偏爱（60∶40）。通过热力学方法，可以通过酸促进的平衡，C23差向异构体的色谱分离以及不希望的异构体重新达到平衡条件，从而容易地获得所需的螺缩醛。这种可扩展的合成序列提供了数克的，因此能够成功完成altohyrtin A /海绵体抑素1的总合成，如本系列文章的第4部分所报道。
• Acyclic stereoselection. 20. High diastereofacial selectivity in the stannic chloride mediated reactions of allylsilanes with chiral α- and β-alkoxy aldehydes.
  作者：Syun-ichi Kiyooka、Clayton H Heathcock

  DOI：10.1016/s0040-4039(00)94002-4

  日期：1983.1

  Stannic chloride is an effective catalyst for the reaction of allylsilanes with chiral α- and β-alkoxy aldehydes. In the case of α-alkoxy aldehyde 1, the diastereofacial preference is outstanding (>35:1). With β- alkoxy aldehydes 5 and 6, selectivity is lower, but still quite acceptable (7–12:1).

  氯化锡是烯丙基硅烷与手性α-和β-烷氧基醛反应的有效催化剂。在α-烷氧基醛1的情况下，非对面优先性是突出的（> 35：1）。使用β-烷氧基醛5和6时，选择性较低，但仍然可以接受（7–12：1）。
• Stereoselective Synthesis of C13–C28 Fragment of Marinomycin A
  作者：Akkapalli Rajesh、Gangavaram Sharma、Krishna Damera

  DOI：10.1055/s-0034-1379697

  日期：——
• Addition of Allylindium Reagents to Aldehydes Substituted at C_α or C_β with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems
  作者：Leo A. Paquette、Thomas M. Mitzel

  DOI：10.1021/ja953682c

  日期：1996.1.1

  The stereochemical course of indium-promoted allylations to alpha- and beta-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O. The free hydroxyl derivatives react with excellent diastereofacial control to give significantly heightened levels of syn-1,2-diols and anti-1,3-diols. Relative reactivities were determined in the alpha-series, and the hydroxy aldehyde proved to be the most reactive substrate. This reactivity ordering suggests that the selectivity stems from chelated intermediates. The rate acceleration observed in water can be heightened by initial acidification. Indeed, the indium-promoted allylation reaction mixtures become increasingly acidic on their own. Preliminary attention has been accorded to salt effects, and tetraethylammonium bromide was found to exhibit a positive synergistic effect on product distribution. Finally, mechanistic considerations are presented in order to allow for assessment of the status of these unprecedented developments at this stage of advancement of the field.
• Radical Cyclization of β-Alkoxymethacrylates:  Expedient Synthesis of (+)-Methyl Nonactate
  作者：Eun Lee、Seung Jib Choi

  DOI：10.1021/ol9909536

  日期：1999.10.1

  [GRAPHICS]Radical cyclization of the beta-alkoxymethacrylate obtained from 5-benzyloxy-1-iodohexan-3-ol led to the stereoselective preparation of the benzyl ether of (+)-methyl nonactate, demonstrating "2,5-cis" selectivity in the radical cyclization step in forming a tetrahydrofuran ring system and "threo" selectivity in the hydrogen abstraction step.