(E)-6-hydroxy-2-hexenoic acid | 38875-88-6

• 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: (E)-6-hydroxy-2-hexenoic acid
• 英文别名: (E)-6-hydroxyhex-2-enoic acid；6-hydroxyhexenoic acid；(2E)-6-hydroxyhex-2-enoic acid
• CAS: 38875-88-6
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: IXRYCTVGILOOMO-DUXPYHPUSA-N

物化性质

• 沸点：
  81-83 °C(Press: 9 Torr)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-hydroxy-2-hexenoic acid 在 吡啶 、 硫酸 、 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 (E)-6-Iod-2-hexensaeure-methylester
  参考文献：
  名称：

  A highly practical synthesis of natural PGE1, Δ2-trans-PGE1 and 2,2,3,3-tetradehydro-PGE1 via two-component coupling process using zinc-copper reagents

  摘要：

  DOI：

  10.1016/s0040-4039(00)97654-8
• 作为产物：
  描述：

  3,6-二氯-己酸 在 potassium acetate 作用下， 以 乙二醇 为溶剂， 生成 (E)-6-hydroxy-2-hexenoic acid
  参考文献：
  名称：

  Dolezal,S., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3117 - 3121

  摘要：

  DOI：

文献信息

• GENERAL CATALYST FOR C-H FUNCTIONALIZATION
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20160272662A1

  公开（公告）日：2016-09-22

  The invention provides novel manganese catalysts such as [Mn( t BuPc)], which are general for the amination of all types of C(sp 3 )-H bonds (aliphatic, allylic, propargylic, benzylic, ethereal), including strong 1 o aliphatic C—H bonds, while achieving excellent chemoselectivity, stereospecificity, and high functional group tolerance. We demonstrate the late-stage diversification of bioactive complex molecules that encompass the range of C(sp 3 )-H bond types, such as selective 1 o C—H aminations of betulinic acid and pleuromutilin derivatives. The catalysts' unprecedented balance of reactivity and selectivity is in part attributed to its mechanism of C—H amination that lies between stepwise and concerted.

  该发明提供了新型的锰催化剂，如[Mn(tBuPc)]，适用于所有类型的C(sp3)-H键（脂肪族、烯丙基、丙炔基、苄基、乙醚基）的胺化，包括强1°脂肪族C—H键，同时实现优异的化学选择性、立体特异性和高官能团耐受性。我们展示了包括选择性1°C—H键胺化在内的生物活性复合分子的晚期多样化，这些复合分子涵盖了各种C(sp3)-H键类型，如对苯二酚酸和普鲁莫铁霉素衍生物的选择性1°C—H键胺化。催化剂在反应性和选择性之间的前所未有的平衡部分归因于其C—H键胺化机制介于逐步和协同之间。
• Stereoselective Access to Tetrahydropyranylacetic Acid Derivatives. Simple Synthesis of (+)-(<i>S,S</i>)-(<i>cis</i>-6-Methyltetrahydropyran-2- yl)acetic Acid
  作者：Valentine Ragoussis、Vassiliki Theodorou

  DOI：10.1055/s-1993-25803

  日期：——

  The reaction of the lactols 1a-1d, with malonic acid in hot dimethyl sulfoxide, in the presence of piperidinium acetate as catalyst, gives the corresponding (tetrahydrofuran-2-yl)acetic acids 2a,c and (tetrahydropyran-2-yl)acetic acids 2b,d in high yield (65-75%). While the synthesis of the (6-methyltetrahydropyran-2-yl)acetic acid (2d) is highly stereoselective (cis/trans ratio 20:1), no stereoselection was observed with the (5-methyltetrahydrofuran-2-yl)acetic acid (2c) (cis/trans ratio 1:1). This reaction was applied for the synthesis of natural (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid (7), minor constituent of the glandular secretion of the civet cat.

  内酯 1a-1d 在热二甲亚砜中与丙二酸反应，在乙酸哌啶盐作为催化剂的存在下，可以得到相应的（四氢呋喃-2-基）乙酸 2a,c 和（四氢吡喃-2-基）乙酸 2b,d，产率高（65-75%）。(6-甲基四氢吡喃-2-基)乙酸(2d)的合成具有高度的立体选择性（顺式/反式比为 20:1），而(5-甲基四氢呋喃-2-基)乙酸(2c)则没有立体选择性（顺式/反式比为 1:1）。该反应被用于合成天然的(+)-(S,S)-(顺式-6-甲基四氢吡喃-2-基)乙酸(7)，这是狸猫腺体分泌物的次要成分。
• PPAR agonists, compounds, pharmaceutical compositions, and methods of use thereof
  申请人：Mitobridge, Inc.

  公开号：US10188627B2

  公开（公告）日：2019-01-29

  Provided herein are compounds of formula (I) useful for the treatment of PPAR-delta related diseases (e.g. mitochondrial diseases, muscular diseases, vascular diseases, demyelinating diseases and metabolic diseases).

  本文提供的式 (I) 化合物可用于治疗 PPAR-delta 相关疾病（如线粒体疾病、肌肉疾病、血管疾病、脱髓鞘疾病和代谢性疾病）。
• Polyketide synthase encoded by a methymycin/pikromycin biosynthetic gene cluster
  申请人：Regents of the University of Minnesota

  公开号：US20020110897A1

  公开（公告）日：2002-08-15

  A novel pathway for the synthesis of polyhydroxyalkanoates is provided. A method of synthesizing a recombinant polyhydroxyalkanoate monomer synthase is also provided. These recombinant polyhydroxyalkanoate synthases are derived from multifunctional fatty acid synthases or polyketide synthases and generate hydroxyacyl acids capable of polymerization by a polyhydroxyalkanoate synthase. Also provided is a biosynthetic gene cluster for methymycin and pikomycin as well as a biosynthetic gene cluster for desosamine.

  提供了一种合成聚羟基烷酸酯的新途径。还提供了一种合成重组多羟基烷酸单体合酶的方法。这些重组聚羟基烷酸单体合成酶来源于多功能脂肪酸合成酶或聚酮酸合成酶，生成的羟基酰基酸能够被聚羟基烷酸单体合成酶聚合。此外，还提供了甲基霉素和匹考霉素的生物合成基因簇，以及去甲沙明的生物合成基因簇。
• DNA encoding methymycin and pikromycin
  申请人：Regents of the University of Minnesota

  公开号：US20020164742A1

  公开（公告）日：2002-11-07

  A novel pathway for the synthesis of polyhydroxyalkanoates is provided. A method of synthesizing a recombinant polyhydroxyalkanoate monomer synthase is also provided. These recombinant polyhydroxyalkanoate synthases are derived from multifunctional fatty acid synthases or polyketide synthases and generate hydroxyacyl acids capable of polymerization by a polyhydroxyalkanoate synthase. Also provided is a biosynthetic gene cluster for methymycin and pikomycin as well as a biosynthetic gene cluster for desosamine.

  提供了一种合成聚羟基烷酸酯的新途径。还提供了一种合成重组多羟基烷酸单体合酶的方法。这些重组聚羟基烷酸单体合成酶来源于多功能脂肪酸合成酶或聚酮酸合成酶，生成的羟基酰基酸能够被聚羟基烷酸单体合成酶聚合。此外，还提供了甲基霉素和匹考霉素的生物合成基因簇，以及去甲沙明的生物合成基因簇。