Se-phenyl N-methyl-N-[3-(p-chlorophenyl)prop-2-ynyl]carbamoselenoate | 861956-80-1

• 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: Se-phenyl N-methyl-N-[3-(p-chlorophenyl)prop-2-ynyl]carbamoselenoate
• 英文别名: Se-phenyl N-[3-(4-chlorophenyl)prop-2-ynyl]-N-methylcarbamoselenoate
• CAS: 861956-80-1
• 化学式: C₁₇H₁₄ClNOSe
• 分子量: 362.717
• InChiKey: BLJSKSIMJHHLQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Se-phenyl N-methyl-N-[3-(p-chlorophenyl)prop-2-ynyl]carbamoselenoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (E)-1-methyl-3-[(p-chlorophenyl)phenylselenomethylene]azetidin-2-one 、 (Z)-1-methyl-3-[(p-chlorophenyl)phenylselenomethylene]azetidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Selenocarbamoylation of Alkynes with Carbamoselenoates:  Formation of α-Alkylidene-β-lactam Framework

  摘要：

  Pd-catalyzed intramolecular selenocarbamoylation of alkynes leading to alpha-alkylidene-beta-lactams was developed. This reaction can be applied to thiocarbamoylation and to the synthesis of delta- and epsilon-lactams and a cyclobutanone.

  DOI：

  10.1021/ja052175k
• 作为产物：
  描述：

  N-methyl-N-[3-(p-chlorophenyl)prop-2-ynyl]amine 在 吡啶 、 selenium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 0.08h， 生成 Se-phenyl N-methyl-N-[3-(p-chlorophenyl)prop-2-ynyl]carbamoselenoate
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Selenocarbamoylation of Alkynes with Carbamoselenoates:  Formation of α-Alkylidene-β-lactam Framework

  摘要：

  Pd-catalyzed intramolecular selenocarbamoylation of alkynes leading to alpha-alkylidene-beta-lactams was developed. This reaction can be applied to thiocarbamoylation and to the synthesis of delta- and epsilon-lactams and a cyclobutanone.

  DOI：

  10.1021/ja052175k

文献信息

• A new entry to α-alkylidene-β-lactams by 4-exo-dig cyclization of carbamoyl radicals
  作者：Shin-ichi Fujiwara、Yoshihiko Shimizu、Yuji Imahori、Masashi Toyofuku、Tsutomu Shin-ike、Nobuaki Kambe

  DOI：10.1016/j.tetlet.2009.03.071

  日期：2009.7

  A new synthetic method of alpha-alkylidene-beta-lactam frameworks has been developed. Irradiation of carbamotelluroates 5 having a propargylic group at the nitrogen atom with visible light afforded alpha-telluromethylene-beta-lactams 6 by 4-exo-dig cyclization of carbamoyl radicals, generated by homolytic cleavage of carbamoyl carbon-tellurium bond of 5, with internal C-C triple bond. Density functional theory (DFT) calculations on cyclization step indicate that 4-exo-dig cyclization of carbamoyl radicals is kinetically favored. The existence of a rapid equilibrium between carbamoyl and four-membered vinyl radicals was Suggested by control experiments using the corresponding carbamoselenoate. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Intramolecular Selenocarbamoylation of Alkynes with Carbamoselenoates:  Formation of α-Alkylidene-β-lactam Framework
  作者：Masashi Toyofuku、Shin-ich Fujiwara、Tsutomu Shin-ike、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1021/ja052175k

  日期：2005.7.13

  Pd-catalyzed intramolecular selenocarbamoylation of alkynes leading to alpha-alkylidene-beta-lactams was developed. This reaction can be applied to thiocarbamoylation and to the synthesis of delta- and epsilon-lactams and a cyclobutanone.