N-tert-butyloxycarbonyl-4,6-dibromoisatin | 927418-43-7

• 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: N-tert-butyloxycarbonyl-4,6-dibromoisatin
• 英文别名: tert-Butyl 4,6-dibromo-2,3-dioxoindoline-1-carboxylate；tert-butyl 4,6-dibromo-2,3-dioxoindole-1-carboxylate
• CAS: 927418-43-7
• 化学式: C₁₃H₁₁Br₂NO₄
• 分子量: 405.043
• InChiKey: LMPSGVKSCBQOME-UHFFFAOYSA-N

物化性质

• 熔点：
  128-131 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  469.4±55.0 °C(Predicted)
• 密度：
  1.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-4,6-dibromoisatin 在 lithium hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (2,4-Dibromo-6-tert-butoxycarbonylamino-phenyl)-oxo-acetic acid
  参考文献：
  名称：

  Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis

  摘要：

  The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed pi-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.021
• 作为产物：
  描述：

  4,6-二溴靛红 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以100%的产率得到N-tert-butyloxycarbonyl-4,6-dibromoisatin
  参考文献：
  名称：

  Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis

  摘要：

  The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed pi-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.021

文献信息

• Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis
  作者：Giancarlo Cravotto、Giovanni B. Giovenzana、Giovanni Palmisano、Andrea Penoni、Tullio Pilati、Massimo Sisti、Federica Stazi

  DOI：10.1016/j.tetasy.2006.11.021

  日期：2006.11

  The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed pi-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography. (c) 2006 Published by Elsevier Ltd.