tert-butyl N-[(1R)-1-cyclopentyl-2-hydroxyethyl]carbamate | 188347-99-1

• 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: tert-butyl N-[(1R)-1-cyclopentyl-2-hydroxyethyl]carbamate
• CAS: 188347-99-1
• 化学式: C₁₂H₂₃NO₃
• 分子量: 229.32
• InChiKey: PLLUYIVXBHXKFF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1R)-1-cyclopentyl-2-hydroxyethyl]carbamate 在 barium dihydroxide 、 四(三苯基膦)钯 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 3-((R)-2-Amino-2-cyclopentyl-ethyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  3-(2-Aminoalkyl)-1-(2,6-difluorobenzyl)-5- (2-fluoro-3-methoxyphenyl)-6-methyl- uracils as Orally Bioavailable Antagonists of the Human Gonadotropin Releasing Hormone Receptor

  摘要：

  Uracils possessing N-3 side chains derived from various amino alcohols were designed and synthesized as potent human gonadotropin releasing hormone receptor antagonists. The compounds herein presented displayed superior metabolic stability than their predecessor molecules. Selected compounds from this series featured good oral bioavailability in mice and cynomolgus monkeys.

  DOI：

  10.1021/jm049791w
• 作为产物：
  描述：

  在 甲醇 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以74%的产率得到tert-butyl N-[(1R)-1-cyclopentyl-2-hydroxyethyl]carbamate
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Novel compounds as inhibitors of hepatitis C virus NS3 serine protease
  申请人：Arasappan Ashok

  公开号：US20070142300A1

  公开（公告）日：2007-06-21

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
• US7186747B2
  申请人：——

  公开号：US7186747B2

  公开（公告）日：2007-03-06
• US7425576B2
  申请人：——

  公开号：US7425576B2

  公开（公告）日：2008-09-16
• Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones
  作者：Hirofumi Matsunaga、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/s0040-4020(96)01077-0

  日期：1997.1

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.
• 3-(2-Aminoalkyl)-1-(2,6-difluorobenzyl)-5- (2-fluoro-3-methoxyphenyl)-6-methyl- uracils as Orally Bioavailable Antagonists of the Human Gonadotropin Releasing Hormone Receptor
  作者：Fabio C. Tucci、Yun-Fei Zhu、Zhiqiang Guo、Timothy D. Gross、Patrick J. Connors,、Yinghong Gao、Martin W. Rowbottom、R. Scott Struthers、Greg J. Reinhart、Qiu Xie、Ta Kung Chen、Haig Bozigian、Anne L. Killam Bonneville、Andrew Fisher、Liping Jin、John Saunders、Chen

  DOI：10.1021/jm049791w

  日期：2004.7.1

  Uracils possessing N-3 side chains derived from various amino alcohols were designed and synthesized as potent human gonadotropin releasing hormone receptor antagonists. The compounds herein presented displayed superior metabolic stability than their predecessor molecules. Selected compounds from this series featured good oral bioavailability in mice and cynomolgus monkeys.