132(S)-hydroxychlorophyllone a | 127266-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 132(S)-hydroxychlorophyllone a
• 英文别名: chlorophyllone-A；13²(S)-hydroxychlorophyllone a
• CAS: 127266-93-7；134454-36-7
• 化学式: C₃₃H₃₂N₄O₃
• 分子量: 532.642
• InChiKey: BYAAWIHEOPCXLJ-MNLGKLJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  40.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111.73
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  132(S)-hydroxychlorophyllone a 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  叶绿素-a，一种新的脱镁叶绿酸-a相关化合物，从中分离出作为抗氧化化合物

  摘要：

  从短颈蛤的提取物中分离出一种新的脱镁叶绿素相关化合物，称为叶绿素a（1），C 33 H 32 N 4 O 3作为抗氧化化合物。这表明了叶绿素的新降解途径。

  DOI：

  10.1016/s0040-4039(00)88754-7
• 作为产物：
  描述：

  methyl pyropheophorbide a 在 sodium dihydrogenphosphate 、 (+)-(10-camphorsulfonyl) oxaziridine 、 sodium hexamethyldisilazane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 12.3h， 生成 132(S)-hydroxychlorophyllone a
  参考文献：
  名称：

  Stereoselective Synthesis of New Chlorophyll a Related Antioxidants Isolated from Marine Organisms

  摘要：

  A new class of natural antioxidants, chlorophyll a related chlorins 3, 4(S), 4(R), 5(R), 6, 7, 8, and 9, have been synthesized from a chlorophyll a degradation product, pheophorbide a methyl ester (1). Claisen-type intramolecular condensation of pyropheophorbide a methyl ester (2) afforded the common intermediate enol 3. Chlorin 1 and enol 3 have a propensity to undergo exocyclic ring opening by ionic bases. The organic base DBU was found to be an efficient reagent for promoting the asymmetric hydroxylation of these chlorins, using N-sulfonyloxaziridines, without cleavage of the exocyclic rings. Model studies for hydroxylactonization have shown that periodate oxidation of hydroxy ketone 10 stereoselectively and predominantly forms hydroxy lactone 17(S). Periodate oxidation of alpha-hydroxy 1,3-diketone 4(R) and/or 4(S) to furnish hydroxy lactone 5(R) and diketone 7 was found out to be regioselective, and the site of reaction depends on the appropriate choice of reaction media. H-1 NMR spectra have provided information on the absolute configuration of diastereomers at the C-13(2) or C-15(1) position.

  DOI：

  10.1021/jo951854i

文献信息

• Asymmetric hydroxylation of chlorophyll derivatives: A facile entry to both diastereomers of chlorophyllone a
  作者：Lifu Ma、David Dolphin

  DOI：10.1016/0957-4166(95)00001-6

  日期：1995.2

  High stereoselectivity is observed for the asymmetric oxidation of chlorophyll enolates derived from 13(2),17(3)-pheophorbide a enol (3), pheophorbide a methyl ester (8) and pheophytin a (9) with DBU and N-sulfonyl oxaziridines (4), (5) and (6).