tert-butyl 6-bromo-3-[2-[[1-diethoxyphosphoryl-2-oxo-2-(2-trimethylsilylethoxy)ethyl]amino]-2-oxoethyl]-2-[(Z)-3-(4-formyl-1H-imidazol-5-yl)-3-methylbut-1-enyl]indole-1-carboxylate | 916244-36-5

• 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: tert-butyl 6-bromo-3-[2-[[1-diethoxyphosphoryl-2-oxo-2-(2-trimethylsilylethoxy)ethyl]amino]-2-oxoethyl]-2-[(Z)-3-(4-formyl-1H-imidazol-5-yl)-3-methylbut-1-enyl]indole-1-carboxylate
• CAS: 916244-36-5
• 化学式: C₃₅H₅₀BrN₄O₉PSi
• 分子量: 809.767
• InChiKey: JZXQJXQSTNNFPO-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-bromo-3-[2-[[1-diethoxyphosphoryl-2-oxo-2-(2-trimethylsilylethoxy)ethyl]amino]-2-oxoethyl]-2-[(Z)-3-(4-formyl-1H-imidazol-5-yl)-3-methylbut-1-enyl]indole-1-carboxylate 在 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以56%的产率得到22-O-tert-butyl 11-O-(2-trimethylsilylethyl) (2Z,10Z)-19-bromo-4,4-dimethyl-13-oxo-6,8,12,22-tetrazatetracyclo[13.7.0.05,9.016,21]docosa-1(15),2,5(9),7,10,16(21),17,19-octaene-11,22-dicarboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-Chartelline C

  摘要：

  The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.

  DOI：

  10.1021/ja0659673
• 作为产物：
  描述：

  6-溴吲哚-3-乙酸 在 copper(l) iodide 、 四(三苯基膦)钯 盐酸 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 lithium hydroxide 、 四丁基氟化铵 、 碘 、 silver trifluoromethanesulfonate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 镍 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 39.58h， 生成 tert-butyl 6-bromo-3-[2-[[1-diethoxyphosphoryl-2-oxo-2-(2-trimethylsilylethoxy)ethyl]amino]-2-oxoethyl]-2-[(Z)-3-(4-formyl-1H-imidazol-5-yl)-3-methylbut-1-enyl]indole-1-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-Chartelline C

  摘要：

  The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.

  DOI：

  10.1021/ja0659673

文献信息

• Total Synthesis of (±)-Chartelline C
  作者：Phil S. Baran、Ryan A. Shenvi

  DOI：10.1021/ja0659673

  日期：2006.11.1

  The first total synthesis of (+/-)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing monoreduction of an alkyne linker, (3) a simple strategy for placement of the sensitive beta-chloroenamide, (4) an unusually facile thermolysis of a vinyl carboxylic acid, and (5) a powerful ring contraction whose potential utility in heterocyclic chemistry merits further investigation.