(-)-ethyl (tert-butoxycarbonyl)aminocyclopentene-1-carboxylate | 229613-89-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-ethyl (tert-butoxycarbonyl)aminocyclopentene-1-carboxylate
• 英文别名: ethyl (1S,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-ene-1-carboxylate；(-)-Ethyl cis-4-tert-butoxycarbonylamino-2-cyclopentene-1-carboxylate；(1S,4R)-(-)-Ethyl-4-tert-butoxycarbonylaminocyclopent-2-en-1-carboxylate；ethyl (1S,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-ene-1-carboxylate
• CAS: 229613-89-2
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: XAQKSXLQWWIXNN-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-ethyl (tert-butoxycarbonyl)aminocyclopentene-1-carboxylate 在 platinum(IV) oxide 盐酸 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 异氰酸苯酯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 20.0~100.0 ℃ 、689.47 kPa 条件下， 反应 82.17h， 生成 (-)-ethyl (1R,3R,4R)-3-[(1S)-1-acetylamino-2-propylpentyl]-4-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate
  参考文献：
  名称：

  Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo

  摘要：

  Cyclopentane derivatives, designated as BCX-1812, BCX-1827, BCX-1898, and BCX-1923, were tested in parallel with oseltamivir carboxylate and zanamivir for the in vivo activity in mice infected with A/Turkey/Mas/76 X A/Beijing/32/92 (H6N2) influenza virus. The compounds were tested orally and intranasally at different dose levels. BCX-1812, BCX-1827, and BCX-1923 showed more than 50% protection at 1 mg/kg/day dose level on oral treatment. The intranasal treatment was 100% effective even at 0.01 mg/kg/day for all four compounds. On comparison with oseltamivir carboxylate and zanamivir, these four cyclopentane derivatives have shown equal or better efficacies. The synthesis of two new compounds, BCX-1898 and BCX-1923, is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.048
• 作为产物：
  描述：

  (1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(-)-ethyl (tert-butoxycarbonyl)aminocyclopentene-1-carboxylate
  参考文献：
  名称：

  Synthesis of Highly Functionalized Cyclopentanes as Precursors of Hydroxylated Azidocarbonucleosides

  摘要：

  功能化的叠氮氨基醇的区域异构体和立体异构体以对映体纯净的形式合成。非对映体的2-氮杂双环[2.2.1]庚-5-烯-3-酮经过酶促断环反应生成相应的氨基酸和一个对映体的内酰胺，并具有立体选择性。这些化合物通过酯化和氨基甲酰化被保护，随后进行了环氧化。所得的环氧化合物与叠氮化钠发生了互补的立体选择性裂解。区域异构体产物通过结晶或柱色谱法易于分离。

  DOI：

  10.1055/s-0029-1217088

文献信息

• Preparation of substituted cyclopentane and cyclopentene compounds and certain intermediates
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US06762316B1

  公开（公告）日：2004-07-13

  The invention relates to methods for preparing substituted cyclopentene compounds, their intermediates and use as neuraminidase inhibitors.

  本发明涉及制备取代环戊烯化合物的方法，它们的中间体以及作为神经氨酸酶抑制剂的用途。
• SUBSTITUTED CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS USEFUL AS NEURAMINIDASE INHIBITORS
  申请人：BIOCRYST PHARMACEUTICALS INC.

  公开号：EP1040094B9

  公开（公告）日：2015-09-09
• US6562861B1
  申请人：——

  公开号：US6562861B1

  公开（公告）日：2003-05-13
• Synthesis of Highly Functionalized Cyclopentanes as Precursors of Hydroxylated Azidocarbonucleosides
  作者：Ferenc Fülöp、Loránd Kiss、Enikö Forró、Reijo Sillanpää

  DOI：10.1055/s-0029-1217088

  日期：2010.1

  Regio- and stereoisomers of functionalized azido amino alcohols with a cyclopentane skeleton were synthesized in enantiomerically pure forms. Enzymatic ring cleavage of racemic 2-azabicyclo[2.2.1]hept-5-en-3-one gave the corresponding amino acid and one enantiomer of the lactam stereospecifically. These were protected by esterification and carbamoylation, and then epoxidized. The resulting oxiranes underwent cleavage by sodium azide with complementary stereoselectivities. The regioisomeric products were easily separated by crystallization or column chromatography.

  功能化的叠氮氨基醇的区域异构体和立体异构体以对映体纯净的形式合成。非对映体的2-氮杂双环[2.2.1]庚-5-烯-3-酮经过酶促断环反应生成相应的氨基酸和一个对映体的内酰胺，并具有立体选择性。这些化合物通过酯化和氨基甲酰化被保护，随后进行了环氧化。所得的环氧化合物与叠氮化钠发生了互补的立体选择性裂解。区域异构体产物通过结晶或柱色谱法易于分离。
• Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo
  作者：Pooran Chand、Shanta Bantia、Pravin L. Kotian、Yahya El-Kattan、Tsu-Hsing Lin、Yarlagadda S. Babu

  DOI：10.1016/j.bmc.2005.03.048

  日期：2005.6

  Cyclopentane derivatives, designated as BCX-1812, BCX-1827, BCX-1898, and BCX-1923, were tested in parallel with oseltamivir carboxylate and zanamivir for the in vivo activity in mice infected with A/Turkey/Mas/76 X A/Beijing/32/92 (H6N2) influenza virus. The compounds were tested orally and intranasally at different dose levels. BCX-1812, BCX-1827, and BCX-1923 showed more than 50% protection at 1 mg/kg/day dose level on oral treatment. The intranasal treatment was 100% effective even at 0.01 mg/kg/day for all four compounds. On comparison with oseltamivir carboxylate and zanamivir, these four cyclopentane derivatives have shown equal or better efficacies. The synthesis of two new compounds, BCX-1898 and BCX-1923, is also described. (c) 2005 Elsevier Ltd. All rights reserved.