(1R,4R,5S)-1-((S)-1-Hydroxy-allyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione | 223246-04-6

• 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: (1R,4R,5S)-1-((S)-1-Hydroxy-allyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione
• 英文别名: (1R,4R,5S)-1-[(1S)-1-hydroxyprop-2-enyl]-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• CAS: 223246-04-6
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: SWIGNJVYZCQLAW-RXUAOQPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S)-1-((S)-1-Hydroxy-allyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 23.0 ℃ 、101.32 kPa 条件下， 反应 2.0h， 以99%的产率得到(1R,4R,5S)-1-((S)-1-Hydroxy-propyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione
  参考文献：
  名称：

  The structural requirements for inhibition of proteasome function by the lactacystin-derived ?-lactone and synthetic analogs

  摘要：

  The synthesis of analogs of the lactacystin-derived beta-lactone (2) in which the substituents at C(5), C(7) and C(9) were systematically varied has led to a well defined structure-activity correlation for the highly selective inhibition of the mammalian 20 S proteasome. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01142-9
• 作为产物：
  描述：

  (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 在 lithium hydroxide 、 ammonium cerium(IV) nitrate 、 水 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 (1R,4R,5S)-1-((S)-1-Hydroxy-allyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione
  参考文献：
  名称：

  The structural requirements for inhibition of proteasome function by the lactacystin-derived ?-lactone and synthetic analogs

  摘要：

  The synthesis of analogs of the lactacystin-derived beta-lactone (2) in which the substituents at C(5), C(7) and C(9) were systematically varied has led to a well defined structure-activity correlation for the highly selective inhibition of the mammalian 20 S proteasome. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01142-9

文献信息

• The structural requirements for inhibition of proteasome function by the lactacystin-derived ?-lactone and synthetic analogs
  作者：E.J. Corey、Wei-Dong Z. Li、Tohru Nagamitsu、Gabriel Fenteany

  DOI：10.1016/s0040-4020(98)01142-9

  日期：1999.3

  The synthesis of analogs of the lactacystin-derived beta-lactone (2) in which the substituents at C(5), C(7) and C(9) were systematically varied has led to a well defined structure-activity correlation for the highly selective inhibition of the mammalian 20 S proteasome. (C) 1999 Elsevier Science Ltd. All rights reserved.