(3S,4S)-4-[(E,2S,6R,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-4,6,8-trimethyl-10-methylidene-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one | 132950-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,4S)-4-[(E,2S,6R,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-4,6,8-trimethyl-10-methylidene-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one
• CAS: 132950-84-6
• 化学式: C₂₆H₄₆O₄Si
• 分子量: 450.734
• InChiKey: HWSHSXBVZNDASO-PECSFFLOSA-N

物化性质

• 沸点：
  502.9±40.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-[(E,2S,6R,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-4,6,8-trimethyl-10-methylidene-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到
  参考文献：
  名称：

  Total synthesis of the esterase inhibitor (±)-ebelactone a using an aldol-claisen strategy

  摘要：

  The beta-lactone (+/-)-ebelactone A has been prepared in 12 steps from diethylketone (9% overall yield) using a series of three boron enolate aldol reactions coupled with the Ireland ester enolate Claisen rearrangement, 10 --> 11.

  DOI：

  10.1016/s0040-4039(00)88532-9
• 作为产物：
  描述：

  2-乙基丙烯醛 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三甲基氯硅烷 、 双氧水 、 二异丁基氢化铝 、 三乙胺 、 苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 43.33h， 生成 (3S,4S)-4-[(E,2S,6R,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-4,6,8-trimethyl-10-methylidene-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one
  参考文献：
  名称：

  Total synthesis of the esterase inhibitor (±)-ebelactone a using an aldol-claisen strategy

  摘要：

  The beta-lactone (+/-)-ebelactone A has been prepared in 12 steps from diethylketone (9% overall yield) using a series of three boron enolate aldol reactions coupled with the Ireland ester enolate Claisen rearrangement, 10 --> 11.

  DOI：

  10.1016/s0040-4039(00)88532-9

文献信息

• Total Synthesis of (-)-Ebelactone A and B
  作者：Ian Paterson、Alison N. Hulme

  DOI：10.1021/jo00116a010

  日期：1995.6

  The beta-lactone enzyme inhibitors (-)-ebelactone A (1) and (-)-ebelactone B (2) have been prepared in 12 steps from diethyl ketone (4 and 3% overall yield, respectively). The synthetic strategy adopted for the ebelactones demonstrates the use of reagent- and substrate-derived stereocontrol and requires the minimal use of protecting groups. The stereocenters at C-2, C-3, C-8, C-10, and C-11 were constructed using boron aldol methodology. An asymmetric syn, aldol addition of diethyl ketone to 2-ethyl/acrolein gave adduct 8 in 86% ee, followed by a diastereoselective syn aldol reaction to give 11. Subsequently, an Ireland-Claisen rearrangement was used to relay 1,2-syn into 1,5-syn relative stereochemistry, as in 12 --> 14. In the anti aldol construction of the C-2-C-3 bond, the use of either a propionate or butyrate thioester enolate allowed for a divergent approach from aldehyde 17 to both (-)-ebelactone A and B. Several novel analogues of ebelactone A and B were also prepared with inverted stereochemistry at C-2, C-3, or C-12.
• PATERSON, IAN;HULME, ALISON N., TETRAHEDRON LETT., 31,(1990) N1, C. 7513-7516
  作者：PATERSON, IAN、HULME, ALISON N.

  DOI：——

  日期：——
• Total synthesis of the esterase inhibitor (±)-ebelactone a using an aldol-claisen strategy
  作者：Ian Paterson、Alison N. Hulme

  DOI：10.1016/s0040-4039(00)88532-9

  日期：1990.1

  The beta-lactone (+/-)-ebelactone A has been prepared in 12 steps from diethylketone (9% overall yield) using a series of three boron enolate aldol reactions coupled with the Ireland ester enolate Claisen rearrangement, 10 --> 11.