16-十七碳烯-1,2,4-三醇 | 24607-08-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 16-十七碳烯-1,2,4-三醇
• 英文名称: avocadene
• 英文别名: (R,R)-1,2,4-Trihydroxy-16-heptadecene；(2R,4R)-heptadec-16-ene-1,2,4-triol
• CAS: 24607-08-7
• 化学式: C₁₇H₃₄O₃
• 分子量: 286.455
• InChiKey: DFEHQWFIOMAGBM-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-十七碳烯-1,2,4-三醇 在 二正丁基氧化锡 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以85%的产率得到(3S,5S)-5-(12-tridecenyl)-tetrahydrofuran-3-ol
  参考文献：
  名称：

  Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols

  摘要：

  Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (Delta A-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.02.083
• 作为产物：
  描述：

  13-bromo-1-tridecene 在 吡啶 、 氢氧化钾 、 对甲苯磺酸 、 magnesium 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙醚 、 乙醇 、 水 、 苯 为溶剂， 反应 5.0h， 生成 16-十七碳烯-1,2,4-三醇
  参考文献：
  名称：

  Sugiyama, Takeyoshi; Sato, Akemi; Yamashita, Kyohei, Agricultural and Biological Chemistry, 1982, vol. 46, # 2, p. 481 - 486

  摘要：

  DOI：

文献信息

• <i>De Novo</i> Asymmetric Synthesis of Avocadyne, Avocadene, and Avocadane Stereoisomers
  作者：Vitor L. S. Cunha、Xiaofan Liu、Todd L. Lowary、George A. O’Doherty

  DOI：10.1021/acs.joc.9b02391

  日期：2019.12.6

  The de novo asymmetric synthesis of all possible stereoisomers of two polyketide natural products, avocadyne, avocadene, and the saturated variant avocadane, is described. The stereodivergent synthesis of the 12 congeners is accomplished in 4–6 steps from an achiral acylpyruvate derivative, which, in turn, is prepared in five steps from commercially available materials. The approach uses, sequentially

  描述了两种聚酮化合物天然产物（阿瓦卡丁，阿伏卡汀和饱和变体阿瓦卡丹）的所有可能的立体异构体的从头不对称合成。12种同类物的立体发散合成是通过非手性酰丙酮酸衍生物以4–6步完成的，而该手性酰丙酮酸衍生物又是由市售材料以5步制备的。该方法依次使用Noyori不对称还原，β-羟基酮的非对映选择性螯合或定向还原，以及酯还原成伯醇。
• Antimicrobial, antibacterial and spore germination inhibiting activity from an avocado extract enriched in bioactive compounds
  申请人：INSTITUTO TECNOLOGICO Y DE ESTUDIOS SUPERIORES DE MONTERREY

  公开号：US10575521B2

  公开（公告）日：2020-03-03

  The present disclosure relates to extracts from Persea sp. (avocado) enriched in bioactive compounds which can be used as antimicrobial, antibacterial or spore germination inhibiting agents, the process for obtaining the extracts, acetogenins and isolated molecules and methods for using the extracts enriched in bioactive compounds for providing antimicrobial, antibacterial or spore germination inhibiting effect.

  本公开涉及富含生物活性化合物（可用作抗菌剂、抑菌剂或孢子萌发抑制剂）的牛油果提取物、提取物、乙酰皂苷元和分离分子的获取过程，以及使用富含生物活性化合物的提取物提供抗菌剂、抑菌剂或孢子萌发抑制效果的方法。
• Heptadecanols from the leaves of Persea americana var. americana
  作者：Tzong-Huei Lee、Yow-Fu Tsai、Tzu-Tien Huang、Pi-Yu Chen、Wen-Li Liang、Ching-Kuo Lee

  DOI：10.1016/j.foodchem.2011.11.067

  日期：2012.5

  From the leaves of Persea americana var. americana, eleven heptadecanol derivatives were identified. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configurations were determined by chemical reaction, NOESY experiment and further comparison of the optical rotation value with the literature value. Additionally, the ratios of the contents of six heptadecanol derivatives in leaves, immature fruits, mature fruits and seeds of P. americana were estimated by LC-MS in multiple reaction monitoring (MRM) mode. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
• ANTIMICROBIAL, ANTIBACTERIAL AND SPORE GERMINATION INHIBITING ACTIVITY FROM AN AVOCADO EXTRACT ENRICHED IN BIOACTIVE COMPOUNDS
  申请人：ESTUDIOS SUPERIORES DE MONTERREY INSTITUTO TECNOLOGICO Y DE

  公开号：US20130216488A1

  公开（公告）日：2013-08-22

  The present disclosure relates to extracts from Persea sp. (avocado) enriched in bioactive compounds which can be used as antimicrobial, antibacterial or spore germination inhibiting agents, the process for obtaining the extracts, acetogenins and isolated molecules and methods for using the extracts enriched in bioactive compounds for providing antimicrobial, antibacterial or spore germination inhibiting effect.
• Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols
  作者：Makhosazana P. Gamedze、Comfort M. Nkambule

  DOI：10.1016/j.tetlet.2015.02.083

  日期：2015.4

  Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (Delta A-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields. (C) 2015 Elsevier Ltd. All rights reserved.