[(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxyhexa-1,5-dien-3-yl] prop-2-enoate | 851040-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxyhexa-1,5-dien-3-yl] prop-2-enoate
• CAS: 851040-38-5
• 化学式: C₁₅H₂₆O₃Si
• 分子量: 282.455
• InChiKey: JHSBSPOJFKUGGW-CHWSQXEVSA-N

物化性质

• 沸点：
  305.8±42.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  [(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxyhexa-1,5-dien-3-yl] prop-2-enoate 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride 、 palladium on activated charcoal 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 AD-mix-β 、 氢气 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 、 苯 为溶剂， -10.0~80.0 ℃ 、101.33 kPa 条件下， 反应 52.08h， 生成 (5R)-5-[(1R,12R)-1-[tert-butyl(dimethyl)silyl]oxy-12,13-dihydroxytridecyl]oxolan-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Rollicosin

  摘要：

  The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.

  DOI：

  10.1021/ol047352l
• 作为产物：
  描述：

  (3R,4R)-1,5-hexadiene-3,4-diol 在 咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 [(3R,4R)-4-[tert-butyl(dimethyl)silyl]oxyhexa-1,5-dien-3-yl] prop-2-enoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Rollicosin

  摘要：

  The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.

  DOI：

  10.1021/ol047352l

文献信息

• Asymmetric Total Synthesis of Rollicosin
  作者：Kevin J. Quinn、André K. Isaacs、Brian A. DeChristopher、Stephanie C. Szklarz、Rebecca A. Arvary

  DOI：10.1021/ol047352l

  日期：2005.3.1

  The first total synthesis of rollicosin, a member of a rare subgroup of Annonaceous acetogenins containing two terminal gamma-lactones, is reported. The approach features a highly regio- and stereoselective tandem ring-closing/cross-metathesis reaction for construction of the east-wing lactone and incorporation of the alkyl spacer. Establishment of the C4 stereocenter and addition of the west-wing lactone were achieved by Sharpless asymmetric dihydroxylation and enolate alkylation.