(E)-2,7-octadienyl methyl carbonate | 92747-31-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (E)-2,7-octadienyl methyl carbonate
• 英文别名: methyl [(2E)-octa-2,7-dienyl] carbonate
• CAS: 92747-31-4
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BACCQUAKLSJXND-BQYQJAHWSA-N

物化性质

• 沸点：
  239.2±29.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2,7-octadienyl methyl carbonate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 sodium tetrahydroborate 、 臭氧 作用下， 以 溶剂黄146 为溶剂， 反应 20.25h， 生成 2-[(1S,2R)-2-(hydroxymethyl)cyclopentyl]acetic acid
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8
• 作为产物：
  描述：

  (E)-1-acetoxy-2,7-octadiene 、 氯甲酸甲酯 生成 (E)-2,7-octadienyl methyl carbonate
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8

文献信息

• Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals
  作者：Jro Tsuji、Kazuhiko Takahashi、Ichiro Minami、Isao Shimizu

  DOI：10.1016/s0040-4039(01)81518-5

  日期：——

  Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.

  在钯-膦催化剂存在下于二恶烷中使乙烯酮甲硅烷基缩醛与碳酸烯丙酯反应，以高收率得到α-烯丙基酯。当用无膦的钯催化剂在腈中进行反应时，以良好的产率获得α，β-不饱和酯。
• Molybdenum- and Tungsten-Catalyzed Allylation of Aromatic Compounds with Allylic Esters and Alcohols
  作者：Isao Shimizu、Toshiaki Sakamoto、Saeko Kawaragi、Yooichiro Maruyama、Akio Yamamoto

  DOI：10.1246/cl.1997.137

  日期：1997.2

  A novel method to substitute aromatic compounds with allylic groups using oxygen-containing allylic compounds in the presence of molybdenum or tungsten carbonyls under neutral conditions has been developed. The method is applicable to one step synthesis of methyl eugenol.

  已经开发了一种在中性条件下在钼或钨羰基化合物存在下使用含氧烯丙基化合物用烯丙基取代芳族化合物的新方法。该方法适用于甲基丁香酚的一步合成。
• PALLADIUM-CATALYZED ALLYLATION OF KETONES AND ALDEHYDES WITH ALLYLIC CARBONATES VIA SILYL ENOL ETHERS UNDER NEUTRAL CONDITIONS
  作者：Jiro Tsuji、Ichiro Minami、Isao Shimizu

  DOI：10.1246/cl.1983.1325

  日期：1983.8.5

  Silyl enol ethers are converted to 2-allyl ketones and aldehydes by the reaction with allylic carbonates in the presence of a palladium-phosphine catalyst.

  在钯-膦催化剂存在下，甲硅烷基烯醇醚通过与烯丙基碳酸酯反应转化为 2-烯丙基酮和醛。
• REGIOSELECTIVE SYNTHESIS OF 1-OLEFINS BY PALLADIUM-CATALYZED HYDROGENOLYSIS OF TERMINAL ALLYLIC COMPOUNDS WITH AMMONIUM FORMATE
  作者：Jiro Tsuji、Isao Shimizu、Ichiro Minami

  DOI：10.1246/cl.1984.1017

  日期：1984.6.5

  Various terminal allylic compounds such as allylic esters, phenyl ethers, carbonates, chlorides, and vinyl epoxides react with ammonium or sodium formate to give 1-olefins with high regioselectivity by using palladium–tributylphosphine complex as a catalyst. The reaction offers a useful synthetic method for 1-olefins.

  以钯-三丁基膦配合物为催化剂，烯丙基酯、苯基醚、碳酸酯、氯化物和乙烯基环氧化物等各种末端烯丙基化合物与甲酸铵或甲酸钠反应生成具有高区域选择性的1-烯烃。该反应提供了一种有用的 1-烯烃合成方法。