(-)-(8R,12R)-methyl 7-hydroxy-9-oxoprost-10-en-1-oate | 1268607-22-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-(8R,12R)-methyl 7-hydroxy-9-oxoprost-10-en-1-oate
• 英文别名: methyl (7R)-7-hydroxy-7-[(1R,2R)-2-octyl-5-oxocyclopent-3-en-1-yl]heptanoate
• CAS: 1268607-22-2
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: XWSBCFNQLDMCDY-DBXWQHBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(8R,12R)-methyl 7-hydroxy-9-oxoprost-10-en-1-oate 在 aluminum oxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (-)methyl 7((2R)-2-n-octyl-5-oxocyclopent-3-enylidene)heptanoate
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007
• 作为产物：
  描述：

  (1'R,2S,3aS,4'R,6aS)-6-(dimethoxyphosphorylmethyl)-1',7',7'-trimethylspiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,2'-bicyclo[2.2.1]heptane]-4-one 在 aluminum amalgam 、 正丁基锂 、 10% palladium on activated carbon 、 氢气 、 lithium perchlorate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 水 为溶剂， 反应 54.42h， 生成 (-)-(8R,12R)-methyl 7-hydroxy-9-oxoprost-10-en-1-oate
  参考文献：
  名称：

  Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826

  摘要：

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.007

文献信息

• Stereocontrolled synthesis of enantiopure anticancer cyclopentenone prostaglandin analogues: (−)- and (+)-TEI-9826
  作者：Remigiusz Żurawiński、Maciej Mikina、Marian Mikołajczyk

  DOI：10.1016/j.tetasy.2010.11.007

  日期：2010.12

  The synthesis of both enantiomers of TEI-9826 has been accomplished in seven steps with an overall yield of 44% starting from diastereomeric camphor protected 3-[(dimethoxyphosphoryl)methyl]-4,5-dihydroxycyclopent-2-enones. The key steps include a fully diastereoselective hydrogenation of the endocyclic carbon-carbon double bond in the cyclopentenone ring controlled with a chiral diol moiety and the conversion of the latter into a new transposed olefinic bond. (C) 2010 Elsevier Ltd. All rights reserved.