methyl (Z)-2,7-octadienoate | 201672-54-0

• 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 (Z)-2,7-octadienoate
• 英文别名: methyl (2Z)-octa-2,7-dienoate
• CAS: 201672-54-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: ACOLHUUSSOODOP-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-2,7-octadienoate 在 mercury(II) perchlorate 、 美雄醇 、 三乙胺 、 sodium nitrite 作用下， 反应 43.42h， 生成
  参考文献：
  名称：

  Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions. 17. The Spiro Mode. Efficient and Highly Selective Synthesis of Azapropellanes

  摘要：

  A new variant of the tandem inter [4 + 2]/intra [3 + 2] nitroalkene cycloaddition has been developed. Intermolecular [4 + 2] cycloaddition of a 2-nitroalkene (bearing an unsaturated ester moiety, the dipolarophile) with a vinyl ether produces a cyclic nitronate substituted at C(3) wherein the only stereogenic center is the anomeric carbon C(6). Since the dipolarophile is attached to a tether extending from the C(3) of the nitronate (a-carbon of the nitroalkene), the intramolecular [3 + 2] cycloaddition affords a spiro tricyclic nitroso acetal. The cycloaddition proceeds smoothly for three- and four-atom tethers to afford five- and six-membered rings. Both E- and Z-unsaturated esters serve well as dipolarophiles, but the E-isomers react more selectively. Hydrogenolysis of the nitroso acetals affords the spiro tricyclic alpha-hydroxy lactams in good yield. Remarkably high levels of asymmetric induction are observed with the use of a chiral vinyl ether derived from (1R,2S)-2-phenylcyclohexanol. The origin of asymmetric induction is a combination of the established face selectivity of the enol ether and the preference for a distal fold of the tether away from the: substituent on the anomeric carbon. The scope and limitations of this transformation and an analysis of the origin of stereoselectivity are provided.

  DOI：

  10.1021/jo9719057
• 作为产物：
  描述：

  methyl 7-hydroxyhept-2-enoate 在 正丁基锂 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (Z)-2,7-octadienoate
  参考文献：
  名称：

  Tandem Inter [4 + 2]/Intra [3 + 2] Cycloadditions. 17. The Spiro Mode. Efficient and Highly Selective Synthesis of Azapropellanes

  摘要：

  A new variant of the tandem inter [4 + 2]/intra [3 + 2] nitroalkene cycloaddition has been developed. Intermolecular [4 + 2] cycloaddition of a 2-nitroalkene (bearing an unsaturated ester moiety, the dipolarophile) with a vinyl ether produces a cyclic nitronate substituted at C(3) wherein the only stereogenic center is the anomeric carbon C(6). Since the dipolarophile is attached to a tether extending from the C(3) of the nitronate (a-carbon of the nitroalkene), the intramolecular [3 + 2] cycloaddition affords a spiro tricyclic nitroso acetal. The cycloaddition proceeds smoothly for three- and four-atom tethers to afford five- and six-membered rings. Both E- and Z-unsaturated esters serve well as dipolarophiles, but the E-isomers react more selectively. Hydrogenolysis of the nitroso acetals affords the spiro tricyclic alpha-hydroxy lactams in good yield. Remarkably high levels of asymmetric induction are observed with the use of a chiral vinyl ether derived from (1R,2S)-2-phenylcyclohexanol. The origin of asymmetric induction is a combination of the established face selectivity of the enol ether and the preference for a distal fold of the tether away from the: substituent on the anomeric carbon. The scope and limitations of this transformation and an analysis of the origin of stereoselectivity are provided.

  DOI：

  10.1021/jo9719057

文献信息

• A simple asymmetric synthesis of cis-2,6-disubstituted tetrahydropyran acetic acid derivatives
  作者：A.J.F. Edmunds、W. Trueb

  DOI：10.1016/s0040-4039(96)02483-5

  日期：1997.2

  A new asymmetric synthesis of functionalised cis-2,6-disubstituted tetrahydropyran acetic acids is described. The utility of the procedure is illustrated by the synthesis of (+) and (-)-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a glandular secretion of the civet cat (Viverra civetta). (C) 1997, Elsevier Science Ltd.
• Reaction of bis(Sym-Collidine)-Bromine(I) Hexafluorophosphate with α-Diazo Esters
  作者：Gérard Rousseau、Jean-Xavier Marie

  DOI：10.1080/00397919908086009

  日期：1999.11

  Reaction of alpha-diazo esters with bis(sym-collidine)bromine(I) hexafluorophosphate in methylene chloride at -40 degrees C led to alpha-bromo-alpha,beta-unsaturated esters.