methyl 4-hydroxyhept-2-ynoate

• 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: methyl 4-hydroxyhept-2-ynoate
• 英文别名: (R)-methyl-4-hydroxyhept-2-ynoate；methyl (4R)-4-hydroxyhept-2-ynoate
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: PEKPYXBSOGMMFO-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丁醛 、 丙炔酸甲酯 在 Dimethylzinc 、 三苯基氧化膦 、 (S,S)-(+)-2,6-双[2-(羟基二苯甲基)-1-吡咯烷基-甲基]-4-甲基苯酚 作用下， 以 甲苯 为溶剂， 反应 25.5h， 以67%的产率得到methyl 4-hydroxyhept-2-ynoate
  参考文献：
  名称：

  （R）-Matsutakeol和调味类似物的一般不对称合成。

  摘要：

  通过将末端炔烃不对称加成到醛中，开发了一种有效的，实用的合成手性松醇和类似物的合成路线。（R）-matsutakeol和其他调味品是由各种烷基醛以高收率（三步法最高可达49.5％）和出色的对映体过量（最高> 99％）合成的。该协议可以用作天然脂肪酸代谢产物和类似物的活性小分子文库的替代性不对称合成方法。这些手性烯丙醇可用于食品分析和筛选昆虫引诱剂。

  DOI：

  10.3390/molecules22030364

文献信息

• Highly enantioselective catalytic methyl propiolate addition to both aromatic and aliphatic aldehydes
  作者：Jian Huang、Siping Wei、Li Wang、Chun Zhang、Shuangxun Li、Pingxian Liu、Xi Du、Qin Wang

  DOI：10.1016/j.tetasy.2016.03.009

  日期：2016.6

  The excellent catalytic effect on methyl propiolate addition to a wide range of aromatic and aliphatic aldehydes promoted by inexpensive and commercially available BINOL-based ligand is reported. The catalyst systems showed high yields and excellent enantioselectivities for aromatic aldehydes, and excellent yields and high enantioselectivities for aliphatic aldehydes. (C) 2016 Elsevier Ltd. All rights reserved.
• Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium(IV) complex of a β-hydroxy amide
  作者：Tao Xu、Chao Liang、Yan Cai、Jian Li、Ya-Min Li、Xin-Ping Hui

  DOI：10.1016/j.tetasy.2009.11.022

  日期：2009.12

  Three chiral beta-hydroxy amide ligands were prepared by the reaction of benzyl chloride with amino alcohols derived from L-tyrosine. The titanium(IV) complex of chiral ligand 4a was found to be an effective catalyst for the asymmetric addition of methyl propiolate, to aliphatic and aromatic aldehydes. The gamma-hydroxy-alpha,beta-acetylenic esters were obtained in excellent enantiomeric excesses (up to 94% ee) under optimized conditions. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs
  作者：Jia Liu、Honglian Li、Chao Zheng、Shichao Lu、Xianru Guo、Xinming Yin、Risong Na、Bin Yu、Min Wang

  DOI：10.3390/molecules22030364

  日期：——

  and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (R)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for

  通过将末端炔烃不对称加成到醛中，开发了一种有效的，实用的合成手性松醇和类似物的合成路线。（R）-matsutakeol和其他调味品是由各种烷基醛以高收率（三步法最高可达49.5％）和出色的对映体过量（最高> 99％）合成的。该协议可以用作天然脂肪酸代谢产物和类似物的活性小分子文库的替代性不对称合成方法。这些手性烯丙醇可用于食品分析和筛选昆虫引诱剂。