(-)-(1S,4R,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-1,4-endo,6-endo-trimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one | 149233-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1S,4R,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-1,4-endo,6-endo-trimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one
• 英文别名: (1R,2R,6R,7S,10R)-2,4,4,7,10-pentamethyl-3,5,8,11-tetraoxatricyclo[5.3.1.02,6]undecan-9-one
• CAS: 149233-68-1
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: BCRYQXDXSLLXFH-GOHNVDQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(1S,4R,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-1,4-endo,6-endo-trimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one 在 盐酸 作用下， 反应 24.0h， 生成 (-)-2,7-dideoxy-2,4-di-C-methyl-L-altro-hept-6-ulosono-1,4-lactone
  参考文献：
  名称：

  Total asymmetric synthesis of polypropionate fragments and doubly branched heptono-1,4-lactones

  摘要：

  2-Cyano-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1'R)-camphanate ((+)-3)and (+)-(1R,4R)-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ((+)-4) were obtained readily from 3,4-dimethylfuran. (+)-3 was converted into 2,7-dideoxy-2,4-di-C-methyl-L-glycero- and D-glycero-L-altro-heptono-1,4-lactone ((+)-17) and ((+)-18).

  DOI：

  10.1016/s0040-4039(00)60444-6
• 作为产物：
  描述：

  (-)-(1S,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-1,6-endo-dimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one 在 甲醇 、 lithium hexamethyldisilazane 作用下， 生成 (-)-(1S,4R,5R,6R,7R)-6-exo,7-exo-(isopropylidenedioxy)-1,4-endo,6-endo-trimethyl-2,8-dioxabicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  Total asymmetric synthesis of polypropionate fragments and doubly branched heptono-1,4-lactones

  摘要：

  2-Cyano-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1'R)-camphanate ((+)-3)and (+)-(1R,4R)-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ((+)-4) were obtained readily from 3,4-dimethylfuran. (+)-3 was converted into 2,7-dideoxy-2,4-di-C-methyl-L-glycero- and D-glycero-L-altro-heptono-1,4-lactone ((+)-17) and ((+)-18).

  DOI：

  10.1016/s0040-4039(00)60444-6

文献信息

• Synthesis of Polypropionate Fragments Containing Tertiary-Alcohol Moieties. Cross-aldolisations with lithium enolates of 7-oxabicyclo[2.2.1]heptan-2-one derivatives
  作者：Philippe Kernen、Pierre Vogel

  DOI：10.1002/hlca.19950780205

  日期：1995.3.22

  into (−)-(3R,4R,5R,6S)-3,4:5,7-bis(isopropylidenedioxy)-4,6-dimethylheptan-2-one ((−)-22), and into (+)-(2R,3R,4R,5S,6S)-3,4:5,6-bis(isopropylidenedioxy)-2,4-dimethylheptanal ((+)-34). Condensation of ((+)-34 with the lithium enolate of (−)-(1R,4R,5S,6R)-6-exo-[(tert-butyl)dimethylsilyloxy]-1,5-endo-dimethyl-7-oxabicyclo[2.2.1] heptan-2-one ((−)-38; derived from (+)-1) gave a 3:2 mixture of aldols (+)-39

  的狄尔斯-阿德耳2,4-二甲基呋喃的加成物1-氰基乙烯基（1' - [R）-camphanate（（+） - （1 - [R，2小号，4 - [R）-2-外型-氰基-1,5-二甲基7-氧杂二环[2.2.1]庚-5-烯-2-内型-基（1' - [R）-camphanate（（+） - 1））转化为（+） - 2,7-二脱氧-2,4- -di- C-甲基-L-甘油-（（+）- 6）和-D-甘油-L- altro-庚酮-1,4-内酯（（+）- 7），变成（-）-（3 [R，4 - [R，5 - [R，6小号）-3,4：5,7-双（异丙基二烯二氧基）-4,6-二甲基庚-2--2-（（-）- 22），并成（+）-（2 R，3 R，4 R，5 S，6 S）-3,4：5,6-双（异丙基二烯二氧基）-2,4-二甲基庚醛（（+）- 34）。（（+）- 34与（-）-（1 R，4 R，5 S，6 R）-6- exo
• Total asymmetric synthesis of polypropionate fragments and doubly branched heptono-1,4-lactones
  作者：Philippe Kernen、Pierre Vogel

  DOI：10.1016/s0040-4039(00)60444-6

  日期：1993.4

  2-Cyano-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1'R)-camphanate ((+)-3)and (+)-(1R,4R)-1,5-dimethyl-7-oxabicyclo[2.2.1]hept-5-en-2-one ((+)-4) were obtained readily from 3,4-dimethylfuran. (+)-3 was converted into 2,7-dideoxy-2,4-di-C-methyl-L-glycero- and D-glycero-L-altro-heptono-1,4-lactone ((+)-17) and ((+)-18).