tert-butyl 5-chloro-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate | 1497420-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: tert-butyl 5-chloro-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate
• 英文别名: tert-butyl 5-chloro-3-[(E,3Z)-3-methoxyiminoprop-1-enyl]indole-1-carboxylate
• CAS: 1497420-45-7
• 化学式: C₁₇H₁₉ClN₂O₃
• 分子量: 334.802
• InChiKey: HKRDWAPTGGCPBG-WWFHDKDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-chloro-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate 以 邻二氯苯 为溶剂， 反应 3.0h， 以55%的产率得到6-chloro-9H-pyrido[2,3-b]indole
  参考文献：
  名称：

  A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes

  摘要：

  Indoles are converted into alpha-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolylaldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 degrees C under microwave irradiation undergo loss of the Boc-group, and 6 pi-electrocyclization to alpha-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).

  DOI：

  10.1021/ol403191k
• 作为产物：
  描述：

  5-氯吲哚-3-甲醛 在 4-二甲氨基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 tert-butyl 5-chloro-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate 、 tert-butyl 5-chloro-3-(3-(methoxyimino)prop-1-en-1-yl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes

  摘要：

  Indoles are converted into alpha-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolylaldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 degrees C under microwave irradiation undergo loss of the Boc-group, and 6 pi-electrocyclization to alpha-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).

  DOI：

  10.1021/ol403191k

文献信息

• A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
  作者：Sophie J. Markey、William Lewis、Christopher J. Moody

  DOI：10.1021/ol403191k

  日期：2013.12.20

  Indoles are converted into alpha-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolylaldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 degrees C under microwave irradiation undergo loss of the Boc-group, and 6 pi-electrocyclization to alpha-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).