(4S,6R)-undec-1-ene-4,6-diol | 934986-27-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S,6R)-undec-1-ene-4,6-diol
• 英文别名: (6R)-undec-1-ene-4,6-diol
• CAS: 934986-27-3
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: XVPWDHAGSBBZCU-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,6R)-undec-1-ene-4,6-diol 在 ruthenium trichloride 、 sodium periodate 、 4-甲基苯磺酸吡啶 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 2-((2R,4R,6R)-6-pentyl-2-phenyl-1,3-dioxan-4-yl)acetic acid
  参考文献：
  名称：

  Stereoselective synthesis towards verbalactone and (+)-(3R,5R)-3-hydroxy-5-decanolide

  摘要：

  The stereoselective synthesis towards biologically active verbalactone and (+)-(3R,5R)-3-hydroxy-5-decanolide has been described. The key functionalities are derived from a chiral-auxiliary mediated acetate aldol addition, an oxa-Michael reaction and a 1,3-syn-reduction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.03.002
• 作为产物：
  描述：

  2,2-dimethyl-4-pentyl-6-prop-2-enyl-1,3-dioxane 在 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 (4S,6R)-undec-1-ene-4,6-diol
  参考文献：
  名称：

  FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives

  摘要：

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.112

文献信息

• Organocatalytic Enantioselective Approach to the Synthesis of Verbalactone and (R)-Massoialactone
  作者：Pradeep Kumar、Anand Harbindu

  DOI：10.1055/s-0030-1260051

  日期：2011.6

  The organocatalytic enantioselective synthesis of verbalactone and (R)-massoialactone is described. The requisite stereogenic centers of the target molecules were constructed using l-proline-catalyzed α-aminoxylation and Horner-Wadsworth-Emmons­ (HWE) olefination. Yamaguchi macrolactonization and ring-closing metathesis were employed as key steps in the syntheses.

  描述了有机催化的对映选择性合成verbalactone和(R)-massoialactone。目标分子的必要立体中心通过l-脯氨酸催化的α-氨基氧化反应和Horner-Wadsworth-Emmons（HWE）烯化反应构建。Yamaguchi大环内酯化和环闭合复分解反应被作为合成中的关键步骤。
• A Short and Highly Diastereoselective Synthesis of Verbalactone
  作者：Janine Cossy、Florent Allais、Marie-Cécile Louvel

  DOI：10.1055/s-2007-967946

  日期：2007.2

  Verbalactone has been synthesized in seven steps in good yield from commercially available hexanal using highly dia­stereo- and enantioselective allylmetalations and a Yamaguchi ­macrolactonization.

  利用高度非对映和对映选择性的烯丙基金属化反应以及 Yamaguchi 大内酯化反应，通过七个步骤从市售己醛中合成了马鞭草内酯，并获得了良好的收率。
• Covalently Immobilized 2‐Deoxyribose‐5‐phosphate Aldolase (DERA) for Biocatalysis in Flow: Utilization of the 3‐Hydroxyaldehyde Intermediate in Reaction Cascades
  作者：Julia Hindges née Bramski、Johannes Döbber、Marc R. Hayes、Thomas Classen、Martina Pohl、Jörg Pietruszka

  DOI：10.1002/cctc.202200390

  日期：2022.8.19

  DERA in Flow: Covalent enzyme immobilization enables reaction cascades to be carried out via the capture of a reactive intermediate species. The combination of continuous biocatalysis and classical chemical transformations both in flow and in batch is shown. Establishment of this reaction protocol allows access to interesting building blocks for natural product synthesis.

  流动中的DERA：共价酶固定化使反应级联能够通过捕获反应性中间物质来进行。显示了连续生物催化和流动和分批的经典化学转化的组合。该反应协议的建立允许访问用于天然产物合成的有趣构建块。
• Methyl (3R,5R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether
  作者：I. V. Mineeva

  DOI：10.1134/s1070428013060067

  日期：2013.6

  A simple and efficient asymmetric synthesis of (5S,7R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3R,5R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.
• FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives
  作者：Amandine Guérinot、Anna Serra-Muns、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2011.03.112

  日期：2011.7

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.