Methyl 3-<2-<(tert-butyldimethylsilyl)oxy>ethyl>indole-1-acetate | 153305-84-1

• 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: Methyl 3-<2-<(tert-butyldimethylsilyl)oxy>ethyl>indole-1-acetate
• 英文别名: Methyl 2-[3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]indol-1-yl]acetate
• CAS: 153305-84-1
• 化学式: C₁₉H₂₉NO₃Si
• 分子量: 347.53
• InChiKey: FSFWUGAKWWDKAL-UHFFFAOYSA-N

物化性质

• 沸点：
  427.0±35.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-3-<(E)-2-(methoxycarbonyl)vinyl>pyridinium chloride 、 Methyl 3-<2-<(tert-butyldimethylsilyl)oxy>ethyl>indole-1-acetate 在 盐酸 、 lithium diisopropyl amide 作用下， 生成 Methyl 3-benzyl-7-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-1β-(methoxycarbonyl)-1,2,3,6-tetrahydro-2,6-methano<1,4>diazocino<4,5-a>indole-5(E)-acrylate 、 Methyl 5-benzyl-7-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-1β-(methoxycarbonyl)-1,2,5,6-tetrahydro-2,6-methanol<1,4>diazocino<1,2-a>indole-3(E)-acrylate 、 Methyl 5-benzyl-7-<2-<(tert-butyldimethylsilyl)oxy>ethyl>-1α-(methoxycarbonyl)-1,2,5,6-tetrahydro-2,6-methano<1,4>diazocino<1,2-a>indole-3(E)-acrylate
  参考文献：
  名称：

  Studies on the synthesis of mavacurine-type indole alkaloids. First total synthesis of (±)-2,7-dihydropleiocarpamine

  摘要：

  Closure of the six-membered C ring of pentacyclic mavacurine-type alkaloids from suitably substituted tetracyclic substructures embodying rings ABDE of these alkaloids, either by electrophilic cyclization upon the indole 3-position or by intramolecular alkylation of the piperidine nitrogen, failed. In contrast, 6a-homopleiocarpamine (45) has been synthesized from dithioacetal 42 by an electrophilic cyclization involving the closure of the seven-membered C ring. The first total synthesis of the alkaloid 2,7-dihydropleiocarpamine (68) has been achieved by photocyclization of the tetracyclic chloroacetamide 54 as the key step. The required tetracyclic ABDE ring systems were prepared by a straightforward sequence consisting of nucleophilic addition of a 1-indoleacetatic ester enolate to the gamma position of a pyridinium salt, acid cyclization of the resulting 1,4-dihydropyridine, and final elaboration of the (E)-ethylidene substituent. An alternative synthesis of the tetracyclic alkaloid vinoxine (10a) is also reported.

  DOI：

  10.1021/jo00079a021
• 作为产物：
  描述：

  色醇 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.75h， 生成 Methyl 3-<2-<(tert-butyldimethylsilyl)oxy>ethyl>indole-1-acetate
  参考文献：
  名称：

  Studies on the synthesis of mavacurine-type indole alkaloids. First total synthesis of (±)-2,7-dihydropleiocarpamine

  摘要：

  Closure of the six-membered C ring of pentacyclic mavacurine-type alkaloids from suitably substituted tetracyclic substructures embodying rings ABDE of these alkaloids, either by electrophilic cyclization upon the indole 3-position or by intramolecular alkylation of the piperidine nitrogen, failed. In contrast, 6a-homopleiocarpamine (45) has been synthesized from dithioacetal 42 by an electrophilic cyclization involving the closure of the seven-membered C ring. The first total synthesis of the alkaloid 2,7-dihydropleiocarpamine (68) has been achieved by photocyclization of the tetracyclic chloroacetamide 54 as the key step. The required tetracyclic ABDE ring systems were prepared by a straightforward sequence consisting of nucleophilic addition of a 1-indoleacetatic ester enolate to the gamma position of a pyridinium salt, acid cyclization of the resulting 1,4-dihydropyridine, and final elaboration of the (E)-ethylidene substituent. An alternative synthesis of the tetracyclic alkaloid vinoxine (10a) is also reported.

  DOI：

  10.1021/jo00079a021

文献信息

• Studies on the synthesis of mavacurine-type indole alkaloids. First total synthesis of (±)-2,7-dihydropleiocarpamine
  作者：M. Lluisa Bennasar、Ester Zulaica、Juan Miguel Jimenez、Joan Bosch

  DOI：10.1021/jo00079a021

  日期：1993.12

  Closure of the six-membered C ring of pentacyclic mavacurine-type alkaloids from suitably substituted tetracyclic substructures embodying rings ABDE of these alkaloids, either by electrophilic cyclization upon the indole 3-position or by intramolecular alkylation of the piperidine nitrogen, failed. In contrast, 6a-homopleiocarpamine (45) has been synthesized from dithioacetal 42 by an electrophilic cyclization involving the closure of the seven-membered C ring. The first total synthesis of the alkaloid 2,7-dihydropleiocarpamine (68) has been achieved by photocyclization of the tetracyclic chloroacetamide 54 as the key step. The required tetracyclic ABDE ring systems were prepared by a straightforward sequence consisting of nucleophilic addition of a 1-indoleacetatic ester enolate to the gamma position of a pyridinium salt, acid cyclization of the resulting 1,4-dihydropyridine, and final elaboration of the (E)-ethylidene substituent. An alternative synthesis of the tetracyclic alkaloid vinoxine (10a) is also reported.