(5S,6R)-erythro-6-acetoxy-5-hexadecanolide | 85551-41-3

• 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: (5S,6R)-erythro-6-acetoxy-5-hexadecanolide
• 英文别名: (+)-(5R,6R)-6-acetoxy-5-hexadecanolide；(5R,6S)-(-)-6-acetoxy-5-hexadecanolide；(5R,6R)-6-acetoxy-5-hexadecanolide；[(1R)-1-[(2R)-6-oxooxan-2-yl]undecyl] acetate
• CAS: 85551-41-3
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: SPOXUSGCKOQPRB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-2-(benzyloxy)dodecanal 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 二甲基硫 、 氢气 、 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 、 乙醚 、 水 、 叔丁醇 、 苯 为溶剂， -78.0~25.0 ℃ 、310.27 kPa 条件下， 反应 6.5h， 生成 (5S,6R)-erythro-6-acetoxy-5-hexadecanolide
  参考文献：
  名称：

  Asymmetric synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, and two of its stereoisomers

  摘要：

  DOI：

  10.1021/jo00376a056

文献信息

• Enantioselective synthesis of mosquito oviposition pheromone and its epimer from a naturally occurring fatty acid
  作者：David Hurem、Travis Dudding

  DOI：10.1039/c5ra19306k

  日期：——

  6S)-5-acetoxy-6-hexadecanolide and its unnatural (5R,6R)-diastereomer in 68% and 54% overall yield by a route involving an organocatalyzed epoxidation of naturally occurring cis-5-hexadecenoic acid and diastereodivergent esterification is reported. The investigation of a dynamic kinetic asymmetric transformation (DYKAT) as an alternate strategy for preparing the target MOPs is also discussed, however this approach

  蚊子产卵信息素（MOP）（5 R，6 S）-5-乙酰氧基-6-十六烷化物及其非天然（5 R，6 R）-非对映异构体的合成，其有机收率可达68％和54％。据报道天然存在的顺式-5-十六碳烯酸的环氧化和非对映异构的酯化反应。还讨论了动态动力学不对称转化（DYKAT）作为制备目标MOP的替代策略的研究，但是由于酮副产物的形成抑制了DYKAT过程中脂肪酶介导的乙酰化步骤，因此该方法未成功。
• Synthesis of both the enantiomers of erythro-6-acetoxy-5-hexadecanolide
  作者：Kenji Mori、Tatsuya Otsuka

  DOI：10.1016/s0040-4020(01)91574-1

  日期：——

  Both (5S, 6R)-(+)- and (5R, 6S)-(−)-6-acetoxy-5-hexadecanolide, the oviposition attractant pheromone of the mosquito Culex pipiens fatigans, were synthesized employing the Sharpless asymmetric epoxidation as the starting step.

  （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。
• Asymmetric total synthesis of all four isomers of 6-acetoxy-5-hexadecanolide: the major component of mosquito oviposition attractant pheromones
  作者：Hong-Bo Dong、Ming-Yan Yang、Xiao-Teng Zhang、Ming-An Wang

  DOI：10.1016/j.tetasy.2014.03.006

  日期：2014.4

  accomplished from readily available hex-5-yn-1-ol via Shi’s asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a–1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5–21.2%, respectively.

  （5不对称全合成小号，6 - [R（+） - - ）赤-6-乙酰氧基-5-十六内酯1A已经从容易得到己-5-炔-1-醇通过施的不对称环氧化反应完成的关键步骤，分八步进行，总产率为33.5％。此外，6-乙酰氧基-5-十六内酯的所有四种异构体的立体选择性合成1A - 1D分别通过Sharpless不对称二羟基化和Mitsunobu反应得到分别作为具有16.5-21.2％的总产率的关键步骤。
• Synthesis of the two enantiomeric forms of erythro-6-acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheramone
  作者：Claudio Fuganti、Piero Grasselli、Stefano Servi

  DOI：10.1039/c39820001285

  日期：——

  The synthesis of the major components of a mosquito oviposition attractant pheromone, (5S,6R)-6-acetoxy-5-hexadecanolide(24) and the (5R,6S)enantiomer (21) from the (2S,3S) C4 aldehyde (1), is reported.

  蚊子产卵引诱信息素的主要组分的合成，（5小号，6 - [R）-6-乙酰氧基-5-十六内酯（24）和（5 - [R，6小号）对映体（21）从（2小号，据报道有3 S）C 4醛（1）。
• COMPOSITIONS AND METHODS FOR DIRECTING THE OVIPOSITION OF MOSQUITOES
  申请人：LAURENTIAN UNIVERSITY

  公开号：US20150359215A1

  公开（公告）日：2015-12-17

  Compositions described herein are purposed to attract gravid mosquitoes to oviposit in a preferred environment. The composition for directing the oviposition of mosquitoes comprises one or more attractants and N—P—K additive, wherein the N—P—K additive is mixture that contain chemical elements nitrogen, phosphorus and potassium. The attractants can be modified to provide a composition for facilitating the oviposition of different kind of mosquito. The composition described above, can be modified to provide a composition for facilitating the oviposition of the Anopheles species of Culicidae. The composition can also include cooked whey, n-heneicosane and/or tetradecanoic acid methyl ester to provide a composition for facilitating the oviposition of the Aedes species of Culicidae. The composition can also be modified to provide a composition for facilitating the oviposition of the Culex species of Culicidae.

  本文描述的组合物旨在吸引孕蚊在优选环境中产卵。用于引导蚊子产卵的组合物包括一种或多种诱引剂和N-P-K添加剂，其中N-P-K添加剂是一种混合物，其中包含化学元素氮、磷和钾。诱引剂可以被修改以提供一种促进不同种类蚊子产卵的组合物。上述组合物可以被修改以提供一种促进疟蚊属蚊子产卵的组合物。该组合物还可以包括煮熟的乳清、正十一烷和/或十四酸甲酯，以提供一种促进伊蚊属蚊子产卵的组合物。该组合物还可以被修改以提供一种促进库蚊属蚊子产卵的组合物。