methyl 4-formyl-6-heptenoate | 65266-23-1

• 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-formyl-6-heptenoate
• 英文别名: methyl 4-formylhept-6-enoate；Methyl-4-formylhept-6-enoat
• CAS: 65266-23-1
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: JXHXTBGCISHWPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-formyl-6-heptenoate 在 sodium sulfate 、 lithium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 75.0 ℃ 、2.0 kPa 条件下， 生成 (3R,8S,8aR)-8-allyl-6-methoxycarbonyl-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine
  参考文献：
  名称：

  An Enantioselective Entry to cis-Perhydroisoquinolines

  摘要：

  [GRAPHICS]An enantioselective route to cis-perhydroisoquinolines, involving a cycloconclensation reaction of (R)-phenylglycinol with a racemic oxoester, a stereoselective conjugate addition to an unsaturated bicyclic lactam, and the closure of the carbocyclic ring by a ring-closing metathesis as the key steps is reported. This route allows the preparation of 3-cyano derivatives as well as cis-octahydroisoquinolines bearing a quaternary center at the N-position.

  DOI：

  10.1021/ol051242c
• 作为产物：
  描述：

  4-戊烯醛 在 potassium carbonate 、 溶剂黄146 作用下， 反应 52.0h， 生成 methyl 4-formyl-6-heptenoate
  参考文献：
  名称：

  合成生物碱的方法：第1部分。v1ncadifformine组的初步研究

  摘要：

  以下论文描述了作为导致18,19-脱氢塔布斯汀全合成工作的序言，有关合成（±）-3-oxo-20-desethyl-20-alylvincadifformine及其C-20的一些较老的工作。报道了差向异构体和（±）-3-氧代-19-乙烯基长春花呢碱。描述了试图通过适当地操作分离的双键将这些化合物转化为各种各样的苯胺丙烯酸酯生物碱，米诺霉素，Tuboxenine和伪甲鱼碱。还研究了在合成的较早阶段使用3,18-二氧-1-脱甲基长春花碱对双键进行功能化的方法。

  DOI：

  10.1016/s0040-4020(01)96091-0

文献信息

• Dynamic Kinetic Resolution and Desymmetrization Processes: A Straightforward Methodology for the Enantioselective Synthesis of Piperidines
  作者：Mercedes Amat、Oriol Bassas、Núria Llor、Margalida Cantó、Maria Pérez、Elies Molins、Joan Bosch

  DOI：10.1002/chem.200600420

  日期：2006.10.16

  A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams that already incorporate carbon substituents on the heterocyclic ring and the subsequent removal of the chiral auxiliary. The key step is a cyclocondensation reaction of (R)-phenylglycinol or other amino alcohols

  报道了合成对映纯多取代哌啶的简单方法。它涉及直接产生已经在杂环上掺入碳取代基的手性非外消旋恶唑并[3，2-a]哌啶酮内酰胺，随后除去手性助剂。关键步骤是（R）-苯基甘醇或其他氨基醇与外消旋或手性δ-氧代（二）酸衍生物在高度立体选择性的过程中进行的环缩合反应，该过程涉及动态动力学拆分和/或非对映体或对映体酯基的去对称化。
• A general synthetic route to enantiopure cis-fused perhydrocycloalka[c]pyridines from phenylglycinol-derived lactams
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Bruno Peretto、Joan Bosch

  DOI：10.1016/j.tet.2007.01.072

  日期：2007.6

  A synthetic route to enantiopure piperidines bearing a five-, six-, or seven-membered carbocyclic ring cis-fused on the c side of the heterocycle from a common phenylglycinol-derived δ-lactam is reported. Key steps are (i) a cyclocondensation reaction of (R)-phenylglycinol with a racemic γ-oxoester in a process that involves a dynamic kinetic resolution; (ii) a highly stereoselective conjugate addition

  据报道，从普通的苯甘醇衍生的δ-内酰胺到杂环的c端带有5、6或7元碳环顺式稠合的对映纯哌啶的合成路线已被报道。关键步骤是（i）（R）-苯基甘氨醇与外消旋γ-氧代酸酯的环缩合反应，该过程涉及动态动力学拆分；（ii）将有机铜酸酯高度立体选择性地共轭加成到不饱和δ-内酰胺上；（iii）闭环烯烃复分解。
• The synthesis of aspidosperma alkaloids containing a functional group at C-18; the total synthesis of (±)-N,O-diacetylcylindrocarpinol, (±)-cylindrocarine, (±)-cylindrocarpine, (±)-cylindrocarpidine, and (±)-20-allyl-20-desethyl-20-epiaspidospermine
  作者：G. Lawton、J.E. Saxton、A.J. Smith

  DOI：10.1016/0040-4020(77)80177-4

  日期：1977.1

  The first total synthesis of (±)-N,O-diacetylcylindrocarpinol 49, (±)-cylindrocarine 51, (±)-cylindrocarpidine 1, and (±)-cylindrocarpine 52, starting from pent-4-enal and proceeding via the ketones 12 and 40, is described. The stereoisomenc ketones 20 and 41 were used as intermediates in a parallel synthesis of (±)-20-allyl-20-desethyl-20-epiaspidospermine 47.

  第一个全合成的（±）-N，O-二乙酰基cylindrocarpinol 49，（±）-cylindrocarine 51，（±）-cylindrocarpidine 1和（±）-cylindrocarpine 52从五元四烯醛开始并通过酮进行。描述图12和40。立体异构体酮20和41用作（±）-20-烯丙基-20-去乙基20-表哌啶子亚胺47的平行合成中的中间体。
• Stereocontrolled synthesis of enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones
  作者：Mercedes Amat、Maria Pérez、Annamaria T. Minaglia、Daniele Passarella、Joan Bosch

  DOI：10.1016/j.tetasy.2008.10.007

  日期：2008.10

  Starting from the 8-allyl substituted oxazolopiperidone lactam 2b, which is easily accessible from (R)-phenylglycinol and racemic delta-oxoester 1a, two-step sequences involving a stereciselective alpha-amidoalkylation reaction, either with inversion or retention Of configuration, followed by a ring-closing metathesis, provide diastereodivergent routes to enantiopure cis- and trans-3,4,4a,5,8,8a-hexahydro-1H-quinolin-2-ones. (C) 2008 Elsevier Ltd. All rights reserved.