3-phenyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone | 88070-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-phenyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone
• 英文别名: (E)-6-(Bromomethylene)tetrahydro-3-phenyl-2H-pyran-2-one；3-Phenyl-6(e)-bromomethylene tetrahydro-pyran-2-one；(6E)-6-(bromomethylidene)-3-phenyloxan-2-one
• CAS: 88070-96-6
• 化学式: C₁₂H₁₁BrO₂
• 分子量: 267.122
• InChiKey: MLLMZYDZKVEZEP-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  2-苯基-5-己炔酸 在 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium hydrogencarbonate 作用下， 生成 3-phenyl-6(E)-(bromomethylidene)tetrahydro-2-pyranone
  参考文献：
  名称：

  Stereoselective Z- and E-bromoenol lactonization of alkynoic acids

  摘要：

  We have found that treatment of the silver salt of a 4- or 5-terminal alkynoic acid with bromine results in clean formation of the corresponding Z-bromo enol lactone, the result of a formal cis addition of carboxylate and bromine across the triple bond. This Z-bromo enol lactonization is highly stereoselective and gives good yields in systems that bear substituents on the internal methylene groups; yields with unsubstituted or terminally substituted alkynoic acids are modest. The E-bromo enol lactonization reaction, reported by us previously (Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459), has a broader scope and, with modifications, can be performed with high reliability. Mercury(II) salts equilibrate the Z- and E-bromo enol lactones, presumedly by a mercuric ion addition-elimination mechanism. These three reactions provide access to an array of stereoisomeric bromo enol lactone systems.

  DOI：

  10.1021/jo00024a035

文献信息

• Stereoselective Z- and E-bromoenol lactonization of alkynoic acids
  作者：Wei Dai、John A. Katzenellenbogen

  DOI：10.1021/jo00024a035

  日期：1991.11

  We have found that treatment of the silver salt of a 4- or 5-terminal alkynoic acid with bromine results in clean formation of the corresponding Z-bromo enol lactone, the result of a formal cis addition of carboxylate and bromine across the triple bond. This Z-bromo enol lactonization is highly stereoselective and gives good yields in systems that bear substituents on the internal methylene groups; yields with unsubstituted or terminally substituted alkynoic acids are modest. The E-bromo enol lactonization reaction, reported by us previously (Krafft, G. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 5459), has a broader scope and, with modifications, can be performed with high reliability. Mercury(II) salts equilibrate the Z- and E-bromo enol lactones, presumedly by a mercuric ion addition-elimination mechanism. These three reactions provide access to an array of stereoisomeric bromo enol lactone systems.
• US5208244A
  申请人：——

  公开号：US5208244A

  公开（公告）日：1993-05-04
• Haloenol pyranones and morpholinones as antineoplastic agents of prostate cancer
  作者：Jason N. Mock、John P. Taliaferro、Xiao Lu、Sravan Kumar Patel、Brian S. Cummings、Timothy E. Long

  DOI：10.1016/j.bmcl.2012.05.038

  日期：2012.7

  Haloenol pyran-2-ones and morpholin-2-ones were synthesized and evaluated as inhibitors of cell growth in two different prostate human cancer cell lines (PC-3 and LNCaP). Analogs derived from Land D-phenylglycine were found to be the most effective antagonists of LNCaP and PC-3 cell growth. Additional studies reveal that the inhibitors induced G2/M arrest and the (S)-enantiomer of the phenylglycine-based derivatives was a more potent inhibitor of cytosolic iPLA(2)beta. Published by Elsevier Ltd.