((1R,2R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-yl)-carbamic acid (1R,2R,3S,4S)-3-hydroxymethyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester | 53398-28-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ((1R,2R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-yl)-carbamic acid (1R,2R,3S,4S)-3-hydroxymethyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
• CAS: 53398-28-0
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: ORLAQERNMCYISW-KIHNPMFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((1R,2R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-yl)-carbamic acid (1R,2R,3S,4S)-3-hydroxymethyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 在 吡啶 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 苯 为溶剂， 生成 ((1R,2R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-yl)-carbamic acid (1R,2R,3S,4S)-3-formyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
  参考文献：
  名称：

  天然和非天然前列腺素的手性经济全合成

  摘要：

  AbstractUsing a meso‐compound which is asymmetrically substituted with a chiral moiety as an intermediate, prostaglandins have been synthesized. Since the undesired enantiomer is readily recycled, this approach leads to a synthesis with high chiral efficiency. In addition it is possible to prepare both enantiomeric configurations of prostaglandins by simply altering the sequence of reactions. This concept should be generally useful in the synthesis of optically active molecules.

  DOI：

  10.1002/hlca.19750580228
• 作为产物：
  描述：

  (1R,2R,6S,7S)-8,9-Dimethyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 红铝 作用下， 以 苯 为溶剂， 生成 ((1R,2R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-yl)-carbamic acid (1R,2R,3S,4S)-3-hydroxymethyl-5,6-dimethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester
  参考文献：
  名称：

  天然和非天然前列腺素的手性经济全合成

  摘要：

  AbstractUsing a meso‐compound which is asymmetrically substituted with a chiral moiety as an intermediate, prostaglandins have been synthesized. Since the undesired enantiomer is readily recycled, this approach leads to a synthesis with high chiral efficiency. In addition it is possible to prepare both enantiomeric configurations of prostaglandins by simply altering the sequence of reactions. This concept should be generally useful in the synthesis of optically active molecules.

  DOI：

  10.1002/hlca.19750580228