Methyl (2R,3R)-1-(tert-butyloxycarbonyl)-3-(hydroxymethyl)aziridine-2-carboxylate | 159763-87-8

• 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 (2R,3R)-1-(tert-butyloxycarbonyl)-3-(hydroxymethyl)aziridine-2-carboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl (2R,3R)-3-(hydroxymethyl)aziridine-1,2-dicarboxylate
• CAS: 159763-87-8
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: GWBPDXWIXMRYLB-IBHKLULDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl (2R,3R)-1-(tert-butyloxycarbonyl)-3-(hydroxymethyl)aziridine-2-carboxylate 在 吡啶 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 Methyl (2R,3S)-1-(tert-butyloxycarbonyl)-3-<1-(3-cyanoindolyl)methyl>aziridine-2-carboxylate
  参考文献：
  名称：

  Cyclization of Chiral Carbon-Centered Aziridinyl Radicals: A New Route to Azirino[2',3':3,4]pyrrolo[1,2-a]indoles

  摘要：

  A carbon-centered aziridinyl radical has been generated from the ester of chiral aziridine carboxylic acid 5b. The resultant radical has been cyclized directly and has been brominated with CBrCl3. The bromo aziridines have also been cyclized reductively in the presence of n-Bu(3)SnH. Dihydroindole 8b bears the same relative and absolute stereochemistry as the mitomycin C nucleus.

  DOI：

  10.1021/jo00105a009
• 作为产物：
  描述：

  Ethyl (2S,3R)-4-hydroxy-2,3-epoxybutyrate 在 咪唑 、 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.25h， 生成 Methyl (2R,3R)-1-(tert-butyloxycarbonyl)-3-(hydroxymethyl)aziridine-2-carboxylate
  参考文献：
  名称：

  Cyclization of Chiral Carbon-Centered Aziridinyl Radicals: A New Route to Azirino[2',3':3,4]pyrrolo[1,2-a]indoles

  摘要：

  A carbon-centered aziridinyl radical has been generated from the ester of chiral aziridine carboxylic acid 5b. The resultant radical has been cyclized directly and has been brominated with CBrCl3. The bromo aziridines have also been cyclized reductively in the presence of n-Bu(3)SnH. Dihydroindole 8b bears the same relative and absolute stereochemistry as the mitomycin C nucleus.

  DOI：

  10.1021/jo00105a009

文献信息

• Chiral Aziridinyl Radicals:  An Application to the Synthesis of the Core Nucleus of FR-900482
  作者：Frederick E. Ziegler、Makonen Belema

  DOI：10.1021/jo961992n

  日期：1997.2.1

  An asymmetric route to the core nucleus of the antitumor agent FR-900482 utilizes the cyclization of an aziridinyl radical into a functionalized indole nucleus. The route employs a selective Polonovski reaction and the Hootele-Dmitrienko rearrangement to install two oxygen atoms.