2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane | 193806-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane
• 英文别名: 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethyl methanesulfonate
• CAS: 193806-50-7
• 化学式: C₁₄H₂₁NO₅S
• 分子量: 315.39
• InChiKey: PFWFFUJXWSVHIM-UHFFFAOYSA-N

物化性质

• 沸点：
  436.8±38.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 tetrafluoroboric acid 、 sodium iodide 、 亚硝酸异戊酯 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 22.0h， 生成 2,3-二氢苯并[b]噻吩
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j
• 作为产物：
  描述：

  2-氨基苯乙醇 在 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 4.33h， 生成 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j

文献信息

• Farnesyl protein transferase inhibitors and methods for treating proliferative diseases
  申请人：Mallams K. Alan

  公开号：US20060211706A1

  公开（公告）日：2006-09-21

  Disclosed are compounds of the Formula: wherein the substituents are as defined herein. Also disclosed are uses of the compounds of formula 1.0 for the manufacture of a medicament for treating cancer and for inhibiting farnesyl protein transferase.

  本发明涉及以下式的化合物：其中取代基如本文所定义。本发明还涉及使用式1.0的化合物制备用于治疗癌症和抑制法尼酰基蛋白转移酶的药物。
• WO2006/65794
  申请人：——

  公开号：——

  公开（公告）日：——
• US7635697B2
  申请人：——

  公开号：US7635697B2

  公开（公告）日：2009-12-22
• Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo970500j

  日期：1997.8.1

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.