(E)-Methyl 4-hydroxyhept-2-enoate | 116261-19-9

• 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)-Methyl 4-hydroxyhept-2-enoate
• 英文别名: methyl (E)-4-hydroxyhept-2-enoate
• CAS: 116261-19-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: NDKPTQNRFWJELN-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  (E)-Methyl 4-hydroxyhept-2-enoate 生成 (R),(E)-Methyl 4-Hydroxyhept-2-enoate
  参考文献：
  名称：

  通过外消旋酯的不对称水解制备（R）-和（S）-（E）-4-羟基-2-不饱和酸

  摘要：

  通过猪胰脂肪酶和对映体的对映选择性水解，由相应的外消旋甲基酯制备了几种光学活性的（R）-和（S）-（E）-4-羟基烷-2-烯酸，它们是脂质过氧化生物活性化合物的代谢物。猪肝酯酶。

  DOI：

  10.1016/s0957-4166(00)80324-9
• 作为产物：
  描述：

  正戊醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 作用下， 以 乙腈 为溶剂， 生成 (E)-Methyl 4-hydroxyhept-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

  摘要：

  DOI：

  10.1016/s0957-4166(00)86334-x

文献信息

• Regiochemical diversity in allylic alkylations via molybdenum catalysts
  作者：Barry M. Trost、Mark Lautens

  DOI：10.1016/s0040-4020(01)87666-3

  日期：1987.1

  the more substituted end of an allyl system regardless of the positional identity of the initial leaving group exists. With β-ketoesters, substrates which possess a secondary and a primary carbon in the allyl unit lead to preferential attack at the secondary carbon. However, substrates that possess a tertiary and a primary carbon at the termini lead to attack at the primary carbon. Anions derived from

  探索了使用钼作为模板来控制烯丙基烷基化反应中的区域选择性。建立了用预先形成的π-烯丙基钼配合物进行烯丙基烷基化的可行性。如在钯反应中一样，添加过量的膦对这些反应的速率有深远的影响。开发了基于六羰基钼的催化反应。使用丙二酸根阴离子时，无论初始离去基团的位置相同如何，在烯丙基系统的更取代末端上的进攻都具有出色的区域选择性。对于β-酮酸酯，在烯丙基单元中具有仲碳和伯碳的底物导致优先攻击仲碳。但是，在末端具有叔碳和伯碳的底物会导致对伯碳的侵蚀。衍生自取代的丙二酸酯和1,3-二酮的阴离子会导致烯丙基系统的取代度较低。强吸电子取代基的存在对这些取向偏差几乎没有影响。讨论了这些结果的机理含义。
• Cross metathesis of allyl alcohols: how to suppress and how to promote double bond isomerization
  作者：Bernd Schmidt、Sylvia Hauke

  DOI：10.1039/c3ob40167g

  日期：——

  formation of ketones, resulting from uncontrolled and undesired double bond isomerization. By conducting the CM in the presence of phenol, the catalyst loading and the reaction time required for quantiative conversion can be reduced, and isomerization can be suppressed. On the other hand, consecutive isomerization can be deliberately promoted by evaporating excess methyl acrylate after completing cross

  在标准条件下，烯丙醇和 丙烯酸甲酯伴随着由于不受控制和不希望的双键异构化导致的酮的形成。通过在以下人员在场的情况下执行CM苯酚，可以减少定量转化所需的催化剂载量和反应时间，并且可以抑制异构化。另一方面，通过过量蒸发可以有意地促进连续的异构化。丙烯酸甲酯 完成交叉复分解后，并添加碱或硅烷作为化学触发剂。
• Allyl Benzenesulfenates in Isomeric Forms
  作者：Rikuhei Tanikaga、Aritsune Kaji

  DOI：10.1246/cl.1988.677

  日期：1988.4.5

  Allyl benzenesulfenates containing an electron-withdrawing group at the conjugated position were prepared in isomeric forms which would be stabilized by partial bonding between the C=C bond and two lone pairs of electrons on the sulfur atom.

  在共轭位置含有吸电子基团的烯丙基苯磺酸盐以异构体形式制备，该异构体形式将通过 C=C 键和硫原子上的两个孤对电子之间的部分键合来稳定。
• Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog
  作者：Kevin Burgess、Juanita Cassidy、Ian Henderson

  DOI：10.1021/jo00006a017

  日期：1991.3

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).
• A general method for the preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines
  作者：Brian M Mathes、Sandra A Filla

  DOI：10.1016/s0040-4039(02)02655-2

  日期：2003.1

  The preparation of 2,3,5-trisubstituted-furo[3,2-b]pyridines via a Pd(0)-catalyzed intramolecular cyclization of methyl 4-(6-chloro-2-iodopyridin-3-yloxy)-substituted-butenoates 9a-f is described. This approach was both efficient and general, and provided the highly functionalized heterocyclic ring system in high yield. Among the several examples provided is the preparation of 3-[2-(N,N-dimethylamino)ethyl]-5-(4-fluorobenzoyl)amino-2-methylfuro[3,2-b]pyridine 4, a selective 5-HTIF receptor agonist. (C) 2003 Elsevier Science Ltd. All rights reserved.