(2R)-2-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-12-phenylmethoxydodec-2-enyl]-2H-furan-5-one | 851040-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R)-2-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-12-phenylmethoxydodec-2-enyl]-2H-furan-5-one
• CAS: 851040-37-4
• 化学式: C₂₉H₄₆O₄Si
• 分子量: 486.767
• InChiKey: BMSMYOVIUAKDBH-PHLSORPBSA-N

物化性质

• 沸点：
  563.0±30.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-12-phenylmethoxydodec-2-enyl]-2H-furan-5-one 在 palladium on activated charcoal 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 a,6-lutidine 、 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 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 44.75h， 生成 [(2R,13R)-2,13-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[(2R)-5-oxooxolan-2-yl]tridecyl] trifluoromethanesulfonate
  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)-4-((tert-butyldimethylsilyl)oxy)hexa-1,5-dien-3-ol 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 (2R)-2-[(E,1R)-1-[tert-butyl(dimethyl)silyl]oxy-12-phenylmethoxydodec-2-enyl]-2H-furan-5-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

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.