1-phenylpentyl mesylate

• 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: 1-phenylpentyl mesylate
• 英文别名: 1-Phenylpentyl methanesulfonate
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: WUGAQOFLLDVSOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenylpentyl mesylate 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 作用下， 以 甲醇 为溶剂， 以86%的产率得到1-吗啉代-3-哌嗪-1-基-丙烷-1-酮
  参考文献：
  名称：

  Synthesis of Functionalized Heteroaromatics: Application to Formal Total Synthesis of Camptothecin

  摘要：

  卡姆托西汀的正式全合成是通过两种吡啶衍生物的锂化反应和钯催化的吡啶基甲基甲基磺酸酯的羰基化反应实现的。

  DOI：

  10.1055/s-1997-785
• 作为产物：
  描述：

  苯戊醇 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 1-phenylpentyl mesylate
  参考文献：
  名称：

  Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes

  摘要：

  A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.

  DOI：

  10.1021/ja408561b

文献信息

• NOVEL COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1135377A1

  公开（公告）日：2001-09-26
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：ASTRAZENECA UK LTD

  公开号：WO2000034254A1

  公开（公告）日：2000-06-15

  Compounds of formula (I) are disclosed, processes for their preparation, pharmaceutical compositions containing the compounds and the use of the compounds as pharmaceuticals. There are also provided chemical intermediates useful for the preparation of the compounds. The compounds are useful as pharmaceuticals, especially for the treatment of inflammatory disease.
• Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
  作者：Hien-Quang Do、E. R. R. Chandrashekar、Gregory C. Fu

  DOI：10.1021/ja408561b

  日期：2013.11.6

  A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
• Synthesis of Functionalized Heteroaromatics: Application to Formal Total Synthesis of Camptothecin
  作者：Naoko Murata、Takumichi Sugihara、Yoshinori Kondo、Takao Sakamoto

  DOI：10.1055/s-1997-785

  日期：1997.3

  The formal total synthesis of camptothecin was achieved via two types of lithiation reactions of pyridine derivatives and a Pd-catalyzed carbonylation of pyridylmethyl methanesulfonates.

  卡姆托西汀的正式全合成是通过两种吡啶衍生物的锂化反应和钯催化的吡啶基甲基甲基磺酸酯的羰基化反应实现的。