((Z)-(3R,8S)-8-Benzyloxycarbonylamino-9-oxo-2,3,6,7,8,9-hexahydro-oxonin-3-yl)-carbamic acid tert-butyl ester | 219724-10-4

• 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: ((Z)-(3R,8S)-8-Benzyloxycarbonylamino-9-oxo-2,3,6,7,8,9-hexahydro-oxonin-3-yl)-carbamic acid tert-butyl ester
• CAS: 219724-10-4
• 化学式: C₂₁H₂₈N₂O₆
• 分子量: 404.463
• InChiKey: LZQMAGXAYWGXAM-YZBXERDGSA-N

物化性质

• 沸点：
  612.680±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.205±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 ((Z)-(3R,8S)-8-Benzyloxycarbonylamino-9-oxo-2,3,6,7,8,9-hexahydro-oxonin-3-yl)-carbamic acid tert-butyl ester 以 二氯甲烷 为溶剂， 生成 ((Z)-(3S,8R)-8-Amino-2-oxo-2,3,4,5,8,9-hexahydro-oxonin-3-yl)-carbamic acid benzyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones

  摘要：

  As part of a project evaluating medium-ring lactams as constrained peptidomimetics, a novel method for the formation of multisubstituted eight-membered lactams has been developed. N-Protected 7-amino-8-hydroxyoctenoic acids were cyclised to give 8-amino-5,6-dehydro-2-oxocanones which underwent clean intramolecular O-to-N-acyl (lactone-to-lactam) ring contraction to yield 8-hydroxymethyl-6,7-dehydro-2-azocanones, suitable for elaboration to eight-membered lactam dipeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02093-0
• 作为产物：
  描述：

  (R)-4-((Z)-(S)-5-Amino-5-carboxy-pent-1-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 2,4,6-三氯苯甲酰氯 、 溶剂黄146 、 三乙胺 作用下， 以 水 为溶剂， 反应 2.0h， 生成 ((Z)-(3R,8S)-8-Benzyloxycarbonylamino-9-oxo-2,3,6,7,8,9-hexahydro-oxonin-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A novel method for the formation of 2-azocanones by lactone-to-lactam ring contraction of 2-oxonanones

  摘要：

  As part of a project evaluating medium-ring lactams as constrained peptidomimetics, a novel method for the formation of multisubstituted eight-membered lactams has been developed. N-Protected 7-amino-8-hydroxyoctenoic acids were cyclised to give 8-amino-5,6-dehydro-2-oxocanones which underwent clean intramolecular O-to-N-acyl (lactone-to-lactam) ring contraction to yield 8-hydroxymethyl-6,7-dehydro-2-azocanones, suitable for elaboration to eight-membered lactam dipeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02093-0