(R)-3-(benzyloxy)hex-5-enal | 405114-95-6

• 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: (R)-3-(benzyloxy)hex-5-enal
• 英文别名: (3R)-3-phenylmethoxyhex-5-enal
• CAS: 405114-95-6
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: HXMVBDCKVSHFTJ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-(benzyloxy)hex-5-enal 在 ammonium heptamolybdate 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 正丁基锂 、 四甲基乙二胺 、 双氧水 、 叔丁基锂 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 水 、 正戊烷 为溶剂， 反应 22.0h， 生成 (1E,3R,4R,6R)-1-benzenesulfonyl-6-benzyloxy-1-N,N-diisopropylcarbamoyloxy-3-methyl nona-1,8-dien-4-ol
  参考文献：
  名称：

  Diastereoselective Synthesis of Protected syn 1,3-Diols:  Preparation of the C16−C24 Portion of Dolabelides

  摘要：

  We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.

  DOI：

  10.1021/ol017122w
• 作为产物：
  描述：

  (R)-1-((4-methoxybenzyl)oxy)hex-5-en-3-ol 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2-碘酰基苯甲酸 作用下， 生成 (R)-3-(benzyloxy)hex-5-enal
  参考文献：
  名称：

  Diastereoselective Synthesis of Protected syn 1,3-Diols:  Preparation of the C16−C24 Portion of Dolabelides

  摘要：

  We have designed a new method to make synthons encompassing a protected syn 1,3-diol motif and an aldehyde a to the 1,3-dioxane ring. An additional stereocenter was also created, potentially leading to stereochemically defined 1,2,4-triols. This method was successfully applied to the synthesis of the C16-C24 portion of Dolabelides.

  DOI：

  10.1021/ol017122w

文献信息

• Biomimetic Approach Toward Enterocin and Deoxyenterocin
  作者：Antonio Rizzo、Robert J. Mayer、Dirk Trauner

  DOI：10.1021/acs.joc.8b02273

  日期：2019.2.1

  antibiotic activity. The synthesis of a linear polyketide resembling a biosynthetic precursor was achieved using an unusual acyloin reaction. A diazo group was introduced as a protecting group for an enolizable ketone. We were unable to bring about the envisioned biomimetic aldol addition cascade and gained insights into the feasibility of this process by DFT calculations. As an alternative approach to enterocin

  肠球菌素（寻常霉素）是具有显着抗生素活性的结构上显着的天然产物。使用不寻常的酰基胆碱反应可完成类似于生物合成前体的线性聚酮化合物的合成。引入重氮基作为可烯醇化的酮的保护基。我们无法实现设想的仿生羟醛加成反应的级联，并且无法通过DFT计算来了解该工艺的可行性。作为替代肠球蛋白的方法，我们开发了Cu催化的分子内环丙烷化，然后进行MgI 2诱导的裂解，以安装天然产物的2-氧杂双环[3.3.1]壬烷核。
• Stereoselective Synthesis of 1,3-<i>anti</i> Diols by an Ipc-Mediated Domino Aldol-Coupling/Reduction Sequence
  作者：Michael Dieckmann、Dirk Menche

  DOI：10.1021/ol3033303

  日期：2013.1.4

  A novel domino process for 1,3-anti diol synthesis by the union of a methyl ketone with an aldehyde is described. The operationally simple procedure is based on an Ipc-boron-aldol coupling and subsequent Ipc-mediated reduction of the intermediate beta-hydroxy-ketone. The sequence proceeds with excellent anti-selectivities and enables the rapid construction of complex polyketide fragments.
• Studies on C18-C20 Aldol Couplings of Rhizopodin
  作者：Dirk Menche、Michael Dieckmann、Sven Rudolph、Carolin Lang、Wiebke Ahlbrecht

  DOI：10.1055/s-0033-1338493

  日期：——

  The aldol addition of an enol(ate) to a carbonyl compound is one of the most powerful and versatile C-C bond forming reactions. In complex target synthesis the coupling of two chiral partners may complicate the stereochemical outcome by multiple stereoinductions. Here, we report studies on pivotal aldol couplings employed in the rhizopodin synthesis, detailing the various directing effects exerted by the stereogenic centers present in this sterically hindered connection.