(+)-(3aR,4Z,7aS)-4-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-3a,7a-dihydro-1-benzofuran-2,5(3H,4H)-dione | 39012-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (+)-(3aR,4Z,7aS)-4-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-3a,7a-dihydro-1-benzofuran-2,5(3H,4H)-dione
• 英文别名: (+)-cryptocaryone；cryptocaryone；(+) cryptocaryone；(3aR,4Z,7aS)-4-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-3a,7a-dihydro-3H-1-benzofuran-2,5-dione
• CAS: 39012-05-0
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: PTLQMLWEJRHXDU-VHIARPGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (+)-(3aR,4Z,7aS)-4-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-3a,7a-dihydro-1-benzofuran-2,5(3H,4H)-dione 在 溴 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 为溶剂， 以42 mg的产率得到8-bromocryptocaryone
  参考文献：
  名称：

  New cytotoxic flavonoids from Cryptocarya infectoria

  摘要：

  A new dihydrochalcone, two new dihydroflavanones and eight new biflavonoids have been isolated together with cryptocaryone from the cytotoxic methanol extract of Cryptocarya infectoria. The absolute structure of cryptocaryone was established by X-ray analysis of its 8-bromo derivative. The structure of the new compounds were elucidated by spectroscopic means and their absolute stereochemistry was deduced from chemical correlation, circular dichroism data and NOESY experiments. Several compounds displayed significant cytotoxicity and cryptocaryone was shown to possess cytotoxicity towards multi-drug resistant K562-DOX cells. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00596-8
• 作为产物：
  描述：

  (3aR,4Z,7aS)-2-hydroxy-4-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-2,3,3a,7a-tetrahydro-1-benzofuran-5-one 在 N-碘代丁二酰亚胺 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(+)-(3aR,4Z,7aS)-4-[(2E)-1-hydroxy-3-phenylprop-2-en-1-ylidene]-3a,7a-dihydro-1-benzofuran-2,5(3H,4H)-dione
  参考文献：
  名称：

  The first asymmetric total syntheses of both enantiomers of cryptocaryone

  摘要：

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.101

文献信息

• Enantioselective Modular Synthesis of Cyclohexenones: Total Syntheses of (+)-Crypto- and (+)-Infectocaryone
  作者：Géraldine Franck、Kerstin Brödner、Günter Helmchen

  DOI：10.1021/ol101588j

  日期：2010.9.3

  A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the way to (+)-cryptocaryone, a catch and release strategy involving an iodolactonization/elimination and

  描述了环己烯酮的模块化合成，并将其应用于（+）-密码-和（+）-感染三烯酮的第一对映选择性总合成。合成环己酮的关键步骤是铱催化的烯丙基烷基化，亲核烯丙基化和闭环易位。在通往（+）-隐香酮的途中，采用了一种捕获和释放策略，该策略涉及碘内酯化/消除和区域选择性C-酰化。
• The first asymmetric total syntheses of both enantiomers of cryptocaryone
  作者：Hiromichi Fujioka、Kenji Nakahara、Tomohiro Oki、Kie Hirano、Tatsuya Hayashi、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2010.01.101

  日期：2010.4

  The first asymmetric total syntheses of the (+)- and (-)-cryptocaryones are described. Removal of the acetal unit of the enone acetal 5, which was obtained in our previous study from the cyclohexadiene acetal 3, afforded the enone acetal 8 in a one-pot procedure. The acylation of 8 with cinnamoyl chloride and subsequent hydrolysis of the resulting acetal gave the lactol 11. Its oxidation with NIS and tetra-n-butyl-ammonium iodide (TBAI) finally furnished the natural (+)-cryptocaryone 2. The same procedure from ent-3 afforded the unnatural one 1. (C) 2010 Elsevier Ltd. All rights reserved.
• New cytotoxic flavonoids from Cryptocarya infectoria
  作者：Vincent Dumontet、Christiane Gaspard、Nguyen Van Hung、Jacques Fahy、Luba Tchertanov、Thierry Sévenet、Françoise Guéritte

  DOI：10.1016/s0040-4020(01)00596-8

  日期：2001.7

  A new dihydrochalcone, two new dihydroflavanones and eight new biflavonoids have been isolated together with cryptocaryone from the cytotoxic methanol extract of Cryptocarya infectoria. The absolute structure of cryptocaryone was established by X-ray analysis of its 8-bromo derivative. The structure of the new compounds were elucidated by spectroscopic means and their absolute stereochemistry was deduced from chemical correlation, circular dichroism data and NOESY experiments. Several compounds displayed significant cytotoxicity and cryptocaryone was shown to possess cytotoxicity towards multi-drug resistant K562-DOX cells. (C) 2001 Elsevier Science Ltd. All rights reserved.