acetylamino-(4-chloro-indol-3-ylmethyl)-malonic acid diethyl ester | 147663-90-9

• 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: acetylamino-(4-chloro-indol-3-ylmethyl)-malonic acid diethyl ester
• 英文别名: Acetylamino-(4-chlor-indol-3-ylmethyl)-malonsaeure-diaethylester
• CAS: 147663-90-9
• 化学式: C₁₈H₂₁ClN₂O₅
• 分子量: 380.828
• InChiKey: KBZXDKRUVOUMDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  575.4±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  97.49
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  acetylamino-(4-chloro-indol-3-ylmethyl)-malonic acid diethyl ester 在 酪朊酸钠 、 sodium hydroxide 作用下， 生成 4-氯色氨酸
  参考文献：
  名称：

  l-4-chlorotryptophan from immatum of Pisum sativum and reassignment of the absolute stereochemistry of N-malonyl-4-chlorotryptophan

  摘要：

  Free 4-chlorotryptophan (4-Cl-Trp) was isolated from immature seeds of P sativum, identified, and its stereochemistry determined to be L-form. Reinvestigation of the N-malonyl-4-Cl-Trp isolated from the same seeds showed that the stereochemistry of 4-Cl-Trp residue is L-form.

  DOI：

  10.1016/s0040-4039(00)77491-0
• 作为产物：
  描述：

  2-(2-氯-6-硝基苯基)乙醇 在 palladium on activated charcoal 、 tris(triphenylphosphine)ruthenium(II) chloride P(C₄H₉)3 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 生成 acetylamino-(4-chloro-indol-3-ylmethyl)-malonic acid diethyl ester
  参考文献：
  名称：

  l-4-chlorotryptophan from immatum of Pisum sativum and reassignment of the absolute stereochemistry of N-malonyl-4-chlorotryptophan

  摘要：

  Free 4-chlorotryptophan (4-Cl-Trp) was isolated from immature seeds of P sativum, identified, and its stereochemistry determined to be L-form. Reinvestigation of the N-malonyl-4-Cl-Trp isolated from the same seeds showed that the stereochemistry of 4-Cl-Trp residue is L-form.

  DOI：

  10.1016/s0040-4039(00)77491-0

文献信息

• Copper-Catalyzed Radical Cyclization To Access 3-Hydroxypyrroloindoline: Biomimetic Synthesis of Protubonine A
  作者：Xu Deng、Kangjiang Liang、Xiaogang Tong、Ming Ding、Dashan Li、Chengfeng Xia

  DOI：10.1021/ol501287x

  日期：2014.6.20

  An unprecedented copper-catalyzed intramolecular radical cyclization was developed for the synthesis of 3-hydroxypyrroloindoline skeletons in excellent yields. The 3-hydroxyl group was introduced by trapping the radical intermediate with molecular oxygen or TEMPO. This process represents a unique radical oxidation pathway for tryptamine/tryptophan derivatives and allows a rapid biomimetic synthesis of natural product protubonine A.
• Experiments on the synthesis of Bz-substituted indoles and tryptophans. Part III. The synthesis of the four Bz-chloro-indoles and -tryptophans
  作者：H. N. Rydon、J. C. Tweddle

  DOI：10.1039/jr9550003499

  日期：——