(5R,6S)-5,6-dihydroxyhexadecanoic acid | 89163-25-7

• 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: (5R,6S)-5,6-dihydroxyhexadecanoic acid
• CAS: 89163-25-7
• 化学式: C₁₆H₃₂O₄
• 分子量: 288.428
• InChiKey: FPECPZMZBLYRJL-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6S)-5,6-dihydroxyhexadecanoic acid 反应 0.33h， 以100%的产率得到(6S)-6-[(1S)-1-hydroxyundecyl]oxan-2-one
  参考文献：
  名称：

  赤型-6-乙酰氧基-5-十六醇内酯的两种对映体的合成：蚊子产卵引诱剂信息素1的主要成分

  摘要：

  （5 S，6 R）-（+）-和（5 R，6 S）-（-）-6-乙酰氧基-5-十六醇化物（蚊子淡色库蚊的产卵引诱剂信息素）均采用Sharpless合成不对称环氧化为起始步骤。

  DOI：

  10.1016/s0040-4020(01)91574-1
• 作为产物：
  描述：

  (5R,6S)-5,6-diacetoxyhexadecanoic acid 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (5R,6S)-5,6-dihydroxyhexadecanoic acid
  参考文献：
  名称：

  赤型-6-乙酰氧基-5-十六醇内酯的两种对映体的合成：蚊子产卵引诱剂信息素1的主要成分

  摘要：

  （5 S，6 R）-（+）-和（5 R，6 S）-（-）-6-乙酰氧基-5-十六醇化物（蚊子淡色库蚊的产卵引诱剂信息素）均采用Sharpless合成不对称环氧化为起始步骤。

  DOI：

  10.1016/s0040-4020(01)91574-1

文献信息

• A novel alkynylation reaction of epoxy alcohols: use in the synthesis of erythro-6-acetoxyhexadecan-5-olide
  作者：Masahiko Yamaguchi、Ichiro Hirao

  DOI：10.1039/c39840000202

  日期：——

  Lithium acetylides in the presence of BF3·Et2O react with epoxy alcohols derived from (E)-allylic alcohols to give erythro-1,2-diols, a reaction used successfully in the stereoselective synthesis of erythro-hexadecan-5-olide.

  在BF 3 ·Et 2 O存在下，乙炔化锂与衍生自（E）-烯丙基醇的环氧醇反应生成赤型-1,2-二醇，该反应成功地用于立体选择性合成赤型-十六烷-5-醇。
• SYNTHESIS OF BOTH ENANTIOMERS OF ERYTHRO-6-ACETOXY-5-HEXADECANOLIDE, THE MAJOR COMPONENT OF A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE
  作者：Toshio Sato、Makoto Watanabe、Naoki Honda、Tamotsu Fujisawa

  DOI：10.1246/cl.1984.1175

  日期：1984.7.5

  Stereoselective synthesis of both (5S,6R)-(+)- and (5R,6S)-(−)-6-acetoxy-5-hexadecanolides, the major component of a mosquito oviposition attractant pheromone, was achieved from (S)-2-cyclohexen-1-ol.

  (5S,6R)-(+)- 和 (5R,6S)-(-)-6-acetoxy-5-hexadecanolides（蚊子产卵引诱信息素的主要成分）的立体选择性合成是从 (S)- 实现的2-环己烯-1-醇。
• Facile Synthesis of (-)-6-Acetoxy-5-hexadecanolide by Organocatalytic α-Oxygenation-Allylation-RCM Strategy
  作者：Jinsung Tae、Youngju Park

  DOI：10.1055/s-0030-1258248

  日期：2010.11

  An asymmetric total synthesis of (-)-6-acetoxy-5-hexadecanolide has been accomplished by employing a seven-step sequence. Asymmetric α-benzoyloxylation of dodecanal followed by indium-mediated one-pot allylation produces the anti-1,2-diol. The six-membered lactone ring is constructed by RCM reaction.

  通过采用七步顺序完成了 (-)-6-乙酰氧基-5-十六内酯的不对称全合成。十二醛的不对称α-苯甲酰氧基化，然后是铟介导的一锅烯丙基化产生抗1,2-二醇。通过RCM反应构建六元内酯环。
• Improvements in or relating to pheromones
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0194077A1

  公开（公告）日：1986-09-10

  Compounds of formula (II) in which R' represents an alkyl group of 6 to 12 carbon atoms, are of value as mosquito attractants, mosquitoes being attracted to a location where they and/or their eggs or larvae are then destroyed.

  式 (II) 中 R' 代表 6 至 12 个碳原子的烷基的化合物具有诱蚊作用，可将蚊子吸引到一个地方，然后在那里消灭它们和/或它们的卵或幼虫。
• Enzymes in organic synthesis. 27. Lipase-Catalyzed Synthesis of (5R,6S)-6-Acetoxyalkan-5-olides - homologues of the mosquito oviposition attractant pheromone
  作者：B. Henkel、A. Kunath、Hans Schick

  DOI：10.1002/prac.19973390176

  日期：——

  Sixteen homologous (5R*,6S*)-6-hydroxyalkan-5-olides rac-5 and their acetoxy derivatives rac-6 were synthesized from the corresponding methyl (Z)-alk-5-enoates 3 by osmium(VIII) oxide catalyzed cis-hydroxylation to the dihydroxy esters rac-4 and hydrolysis of these esters followed by lactonization. Pancreatin-catalyzed lactonization of the dihydroxy esters rac-4 afforded enantiomerically enriched hydroxy lactones ent-5, five of which were obtained enantiomerically pure by recrystallization. Acetylation of the 6-hydroxyalkan-5-olides rac-5 by vinyl acetate catalyzed by the lipase SP 526 provided enantiomerically enriched 6-acetoxyalkan-5-olides 6 with an enantiomeric excess of more than 90% in nine cases. These compounds are known as mosquito oviposition attractant pheromone (6h) or its homologues.