(4R)-3-benzyl-4-[(benzylamino)methyl]-1,3-thiazolidin-2-one | 646030-83-3

• 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: (4R)-3-benzyl-4-[(benzylamino)methyl]-1,3-thiazolidin-2-one
• CAS: 646030-83-3
• 化学式: C₁₈H₂₀N₂OS
• 分子量: 312.436
• InChiKey: YDXDURMWLUQZKB-QGZVFWFLSA-N

物化性质

• 沸点：
  472.4±47.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4R)-3-benzyl-4-[(benzylamino)methyl]-1,3-thiazolidin-2-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到(4R)-1,3-dibenzyl-4-(sulfanylmethyl)imidazolidin-2-one
  参考文献：
  名称：

  2-Thiazolidinone: a novel thiol protective surrogate of complete atom efficiency, a practical synthesis of (+)-biotin

  摘要：

  2-Thiazolidinone derivatives were shown to be novel protective surrogates of a thiol group in L-cysteine derivatives. After elaboration at the C-4 substituent, the thiol group was completely liberated by simple heating in DMF whose atom efficiency is 100%. A practical synthesis of (+)-biotin was accomplished by the use of the strategy employing 4-functionalized 2-thiazolidinone derivatives as the intermediates, allowing a synthesis of (+)-biotin in 10 steps and in 31%, overall yield. Short steps, high yield, and ease of operation of the present approach Would permit the hitherto most efficient access to (+)-biotin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.202
• 作为产物：
  描述：

  N-benzyl-2-oxo-thiazolidine-4-carboxylic acid 在 吡啶 、 dimethyl sulfide borane 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 生成 (4R)-3-benzyl-4-[(benzylamino)methyl]-1,3-thiazolidin-2-one
  参考文献：
  名称：

  2-Thiazolidinone: a novel thiol protective surrogate of complete atom efficiency, a practical synthesis of (+)-biotin

  摘要：

  2-Thiazolidinone derivatives were shown to be novel protective surrogates of a thiol group in L-cysteine derivatives. After elaboration at the C-4 substituent, the thiol group was completely liberated by simple heating in DMF whose atom efficiency is 100%. A practical synthesis of (+)-biotin was accomplished by the use of the strategy employing 4-functionalized 2-thiazolidinone derivatives as the intermediates, allowing a synthesis of (+)-biotin in 10 steps and in 31%, overall yield. Short steps, high yield, and ease of operation of the present approach Would permit the hitherto most efficient access to (+)-biotin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.202

文献信息

• 2-Thiazolidinone: a novel thiol protective surrogate of complete atom efficiency, a practical synthesis of (+)-biotin
  作者：Masahiko Seki、Mayumi Kimura、Masanori Hatsuda、Shin-ichi Yoshida、Toshiaki Shimizu

  DOI：10.1016/j.tetlet.2003.09.202

  日期：2003.12

  2-Thiazolidinone derivatives were shown to be novel protective surrogates of a thiol group in L-cysteine derivatives. After elaboration at the C-4 substituent, the thiol group was completely liberated by simple heating in DMF whose atom efficiency is 100%. A practical synthesis of (+)-biotin was accomplished by the use of the strategy employing 4-functionalized 2-thiazolidinone derivatives as the intermediates, allowing a synthesis of (+)-biotin in 10 steps and in 31%, overall yield. Short steps, high yield, and ease of operation of the present approach Would permit the hitherto most efficient access to (+)-biotin. (C) 2003 Elsevier Ltd. All rights reserved.