cis-1,3-dibenzyl-5-methyl-4-(2-oxyethyl) imidazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: cis-1,3-dibenzyl-5-methyl-4-(2-oxyethyl) imidazolidin-2-one
• 英文别名: 2-[(4R,5S)-1,3-dibenzyl-5-methyl-2-oxoimidazolidin-4-yl]acetaldehyde
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: SVANUFMLZQZDQB-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1,3-dibenzyl-5-methyl-4-(2-oxyethyl) imidazolidin-2-one 在 六甲基磷酰三胺 、 正丁基锂 、 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.17h， 生成 (4S,5R)-4-((Z)-5-Hydroxy-pent-2-enyl)-5-methyl-imidazolidin-2-one
  参考文献：
  名称：

  Synthesis and biochemical properties of Z- and E-4,5-dehydrodethiobiotin

  摘要：

  Radical species are postulated intermediates in the formation of the carbon-sulfur bonds of biotin. It was of interest to examine the behaviour of unsaturated analogues which should give rise to allylic radicals. The two isomers of 4,5-dehydrodethiobiotin have been synthesized and labelled with C-14 On their carboxylic acid group. When incubated with an in vitro system capable of transforming dethiobiotin into biotin, they covalently label biotin synthase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00100-9
• 作为产物：
  描述：

  (3aS,6aR)-1,3-二苄基四氢-1H-呋喃并[3,4-d]咪唑-2,4-二酮 在 吡啶 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 22.75h， 生成 cis-1,3-dibenzyl-5-methyl-4-(2-oxyethyl) imidazolidin-2-one
  参考文献：
  名称：

  Synthesis of New Biotin Derivatives

  摘要：

  It is now established that the formation of C-S bonds during the conversion of dethiobiotin into biotin involves intermediate carbon radicals. To examine the behavior of dethiobiotin analogs that could lead to allylic and alpha-epoxyradicals, we have synthesized 4,5-dehydrodethiobiotins and the corresponding epoxides and 5,6-dehydrodethiobiotins. All these compounds have been labelled with C-14 On the carboxyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01022-4

文献信息

• Synthesis and biochemical properties of Z- and E-4,5-dehydrodethiobiotin
  作者：Eric Jestin、François Moreau、Dominique Florentin、Andrée Marquet

  DOI：10.1016/0968-0896(96)00100-9

  日期：1996.7

  Radical species are postulated intermediates in the formation of the carbon-sulfur bonds of biotin. It was of interest to examine the behaviour of unsaturated analogues which should give rise to allylic radicals. The two isomers of 4,5-dehydrodethiobiotin have been synthesized and labelled with C-14 On their carboxylic acid group. When incubated with an in vitro system capable of transforming dethiobiotin into biotin, they covalently label biotin synthase. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of New Biotin Derivatives
  作者：François Moreau、Dominique Florentin、Andrée Marquet

  DOI：10.1016/s0040-4020(99)01022-4

  日期：2000.1

  It is now established that the formation of C-S bonds during the conversion of dethiobiotin into biotin involves intermediate carbon radicals. To examine the behavior of dethiobiotin analogs that could lead to allylic and alpha-epoxyradicals, we have synthesized 4,5-dehydrodethiobiotins and the corresponding epoxides and 5,6-dehydrodethiobiotins. All these compounds have been labelled with C-14 On the carboxyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.