(1S,5R,6S)-5-羟基-4-(羟基甲基)-7-氧杂双环[4.1.0]庚-3-烯-2-酮 | 256662-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S,5R,6S)-5-羟基-4-(羟基甲基)-7-氧杂双环[4.1.0]庚-3-烯-2-酮
• 中文别名: 哌嗪,2-[(3-甲氧基-4-甲基苯基)甲基]-
• 英文名称: ent-RKTS-33
• 英文别名: (4R,5R,6R)-5,6-epoxy-4-hydroxy-3-hydroxymethylcyclohex-2-en-1-one；(1S,5R,6S)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 256662-98-3
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: RZGZRGXCPXHJFW-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,5R,6S)-5-羟基-4-(羟基甲基)-7-氧杂双环[4.1.0]庚-3-烯-2-酮 在 pyridinium chlorochromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以41%的产率得到叶点霉素
  参考文献：
  名称：

  Preparation of a synthetic equivalent of chiral methyl 2,5-dihydroxycyclohexane-1,4-dienecarboxylate

  摘要：

  A chiral tricyclic diol, serving as a synthetic equivalent of chiral methyl 2,5-dihydroxycyclohexane- 1,4-dienecarboxylate, has been prepared in both enantiomeric forms by employing a lipase-mediated kinetic resolution in vinyl acetate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00414-0
• 作为产物：
  描述：

  [(1R,2S,3S,4R,6R,8R,9S)-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxo-5-oxatetracyclo[7.2.1.02,8.04,6]dodec-10-en-3-yl] acetate 在 2,6-二甲基吡啶 、 manganese(IV) oxide 、 lithium hydroxide 、 sodium tetrahydroborate 、 二苯醚 、 氢氟酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.75h， 生成 (1S,5R,6S)-5-羟基-4-(羟基甲基)-7-氧杂双环[4.1.0]庚-3-烯-2-酮
  参考文献：
  名称：

  Enantioselective total synthesis of polyoxygenated cyclohexanoids: (+)-streptol, ent-RKTS-33 and putative ‘(+)-parasitenone’. Identity of parasitenone with (+)-epoxydon

  摘要：

  Short, simple and enantioselective syntheses of the natural product (+)-streptol, the non-peptide apoptosis inhibitor ent-RKTS-33 and the putative structure of 'parasitenone' have been accomplished from the readily available chiral building block. 'Parasitenone' has been shown to be identical with the known natural product epoxydon. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.087

文献信息

• Synthesis of (+)-Epoxydon, (-)-Phyllostine, (-)-RKTS 33, and (-)-Parasitenone Featuring Selective Sulfonylation and Oxirane Ring Closure of Aldol Cyclization Products
  作者：Feng Shui、Junhao Jia、Xing Yang、Qin Zhou、Yimin Jiang、Xiaochuan Chen

  DOI：10.1002/ejoc.202000486

  日期：2020.7.15

  (+)‐epoxydon, (–)‐phyllostine, (–)‐RKTS 33, and (–)‐parasitenone, are synthesized from δ‐d‐gluconolactone by two new approaches, which both feature selective sulfonylation and oxirane ring closure on the polyoxygenated aldol cyclization products.

  δ- d-葡糖酸内酯通过两种新方法合成了四种脱水葡糖苷，（+）-环氧树酯，（-）-叶芥子碱，（-）-RKTS 33，和（-）-parasitenone，二者均具有选择性磺酰化和环氧乙烷环封闭多氧化羟醛环化产物。
• Enantioselective total synthesis of polyoxygenated cyclohexanoids: (+)-streptol, ent-RKTS-33 and putative ‘(+)-parasitenone’. Identity of parasitenone with (+)-epoxydon
  作者：Goverdhan Mehta、Shashikant R. Pujar、Senaiar S. Ramesh、Kabirul Islam

  DOI：10.1016/j.tetlet.2005.03.087

  日期：2005.5

  Short, simple and enantioselective syntheses of the natural product (+)-streptol, the non-peptide apoptosis inhibitor ent-RKTS-33 and the putative structure of 'parasitenone' have been accomplished from the readily available chiral building block. 'Parasitenone' has been shown to be identical with the known natural product epoxydon. (c) 2005 Elsevier Ltd. All rights reserved.
• Preparation of a synthetic equivalent of chiral methyl 2,5-dihydroxycyclohexane-1,4-dienecarboxylate
  作者：Naoyuki Yoshida、Hiroyuki Konno、Takashi Kamikubo、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1016/s0957-4166(99)00414-0

  日期：1999.9

  A chiral tricyclic diol, serving as a synthetic equivalent of chiral methyl 2,5-dihydroxycyclohexane- 1,4-dienecarboxylate, has been prepared in both enantiomeric forms by employing a lipase-mediated kinetic resolution in vinyl acetate. (C) 1999 Elsevier Science Ltd. All rights reserved.