2-Trimethylsilylethyl 2-amino-2-diethoxyphosphorylacetate | 916244-34-3

• 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: 2-Trimethylsilylethyl 2-amino-2-diethoxyphosphorylacetate
• CAS: 916244-34-3
• 化学式: C₁₁H₂₆NO₅PSi
• 分子量: 311.39
• InChiKey: GYWQQPQQZKHVBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Trimethylsilylethyl 2-amino-2-diethoxyphosphorylacetate 在 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 溴 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 N,N-二异丙基乙胺 、 calcium carbonate 、 lithium chloride 、 sodium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 34.17h， 生成 2-trimethylsilylethyl (5E,13Z)-9,19-dibromo-6-chloro-12,12-dimethyl-3-oxo-4,8,10,16-tetrazapentacyclo[13.7.0.01,4.07,11.017,22]docosa-5,7(11),8,13,15,17(22),18,20-octaene-5-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
• 作为产物：
  描述：

  2-Benzyloxycarbonylamino-2-(diethoxyphosphinyl)-acetic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-Trimethylsilylethyl 2-amino-2-diethoxyphosphorylacetate
  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.