[4-(tert-butyldimethylsilanyloxy)-cyclopent-2-enyl]carbamic acid tert-butyl ester | 1138344-10-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [4-(tert-butyldimethylsilanyloxy)-cyclopent-2-enyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R,4S)-4-[tert-butyl(dimethyl)silyl]oxycyclopent-2-en-1-yl]carbamate
• CAS: 1138344-10-1
• 化学式: C₁₆H₃₁NO₃Si
• 分子量: 313.513
• InChiKey: XZKIBXPJNGMUNI-QWHCGFSZSA-N

物化性质

• 沸点：
  356.9±42.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-(tert-butyldimethylsilanyloxy)-cyclopent-2-enyl]carbamic acid tert-butyl ester 在 ruthenium trichloride 、 sodium periodate 、 air 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 2.25h， 生成
  参考文献：
  名称：

  Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct

  摘要：

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.013
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (+/-)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到[4-(tert-butyldimethylsilanyloxy)-cyclopent-2-enyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct

  摘要：

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.013

文献信息

• Deprotection of N-BOC compounds
  申请人：Choy Jason Chi-Chung

  公开号：US20090203910A1

  公开（公告）日：2009-08-13

  Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.

  具有叔丁氧羰基保护的含氮有机化合物可以通过在氟代醇溶液中加热来有效去保护。
• Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct
  作者：Weiqiang Huang、Marvin J. Miller

  DOI：10.1016/j.tetasy.2008.12.013

  日期：2008.12

  O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D-amino acids. (C) 2008 Elsevier Ltd. All rights reserved.