(1S,2R)-1-N-carbamylamino-2-indanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S,2R)-1-N-carbamylamino-2-indanol
• 英文别名: 1-((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)urea；[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]urea
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: XTMHJUGLSXLAMY-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-N-carbamylamino-2-indanol 在 盐酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (3aS-顺)-(-)-3,3a,8,8a-四氢-2H-茚并[1,2-d]噁唑-2-酮
  参考文献：
  名称：

  Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative

  摘要：

  Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (+/-)-1-amino-2-indanol. Racemic 1-(N'-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with immobilized Pseudomonas cepacia Lipase in the presence of beta -cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N'-chloroacetyl-N-carbamylamino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), in nearly quantitative yields. The deprotection provided enantiomers of 1-N-carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosation-deaminocyclization reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00454-9
• 作为产物：
  描述：

  (1S,2R)-1-(N'-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate 在 Pseudomonas cepacia lipase 、 sodium methylate 作用下， 以 甲醇 、 phosphate buffer 、 丙酮 为溶剂， 反应 24.0h， 生成 (1S,2R)-1-N-carbamylamino-2-indanol
  参考文献：
  名称：

  Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative

  摘要：

  Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (+/-)-1-amino-2-indanol. Racemic 1-(N'-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with immobilized Pseudomonas cepacia Lipase in the presence of beta -cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N'-chloroacetyl-N-carbamylamino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), in nearly quantitative yields. The deprotection provided enantiomers of 1-N-carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosation-deaminocyclization reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00454-9

文献信息

• Ammonium Chloride‐Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
  作者：Chunling Blue Lan、Karine Auclair

  DOI：10.1002/ejoc.202101059

  日期：2021.10.7

  Ammonium chloride promotes the selective formation of monosubstituted ureas under microwave irradiation. Most nucleophiles, acid-labile functionalities, and protecting groups are well tolerated in this reaction. By avoiding transition metals and mineral acids, this methodology offers a more sustainable alternative for the synthesis of monosubstituted ureas and their analogs.

  氯化铵在微波辐射下促进单取代脲的选择性形成。大多数亲核试剂、酸不稳定官能团和保护基团在该反应中具有良好的耐受性。通过避免过渡金属和无机酸，该方法为合成单取代脲及其类似物提供了一种更可持续的替代方案。
• Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative
  作者：Masumi Suzuki、Chiaki Nagasawa、Takeshi Sugai

  DOI：10.1016/s0040-4020(01)00454-9

  日期：2001.6

  Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (+/-)-1-amino-2-indanol. Racemic 1-(N'-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with immobilized Pseudomonas cepacia Lipase in the presence of beta -cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N'-chloroacetyl-N-carbamylamino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), in nearly quantitative yields. The deprotection provided enantiomers of 1-N-carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosation-deaminocyclization reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.