ES242-4 | 136565-69-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: ES242-4
• 英文别名: atropisomer of ES242-4；(3S,4S)-5-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-4,10-diol
• CAS: 136565-69-0
• 化学式: C₃₂H₃₄O₁₀
• 分子量: 578.616
• InChiKey: AVAQRWVGWWNBIN-CUAUGLLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one 在 palladium on activated charcoal 三乙基硅烷 、 sodium hydroxide 、 1,4-环己二烯 、 氧气 、 phosphorus pentoxide 、 二异丁基氢化铝 、 potassium carbonate 、 乙酰氯 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 42.0h， 生成 ES242-4
  参考文献：
  名称：

  The first total synthesis of a bioxanthracene (−)-ES-242-4, an N-methyl-D-aspartate receptor antagonist

  摘要：

  Bioxanthracene (-)-ES-242-4 has been synthesized from oxidative dimerization of a naphthopyran which was derived from an alpha,beta-unsaturated lactone and methyl 2,4-dimethoxy-6-methylbenzoate through tandem Michael-Dieckmann reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00040-9

文献信息

• ES-242 Derivatives and Cycloheptapeptides from <i>Cordyceps</i> sp. Strains BCC 16173 and BCC 16176
  作者：Masahiko Isaka、Urarat Srisanoh、Nattapat Lartpornmatulee、Tanapong Boonruangprapa

  DOI：10.1021/np070357h

  日期：2007.10.1

  Five new ES-242 analogues (1-5) were isolated together with nine known compounds (6-14) from the insect pathogenic fungus Cordyceps sp. BCC 16173. A closely related strain, BCC 16176, provided cordyheptapeptide A (15) and small amount of its new analogue, cordyheptapeptide B (16), along with known ES-242s. Structures of the new bioxanthracenes, 1-5, were determined to be 6'-O-desmethyl analogues of 6 (ES-242-4), 8, 9 (ES-242-2), 12, and 13, respectively, primarily by spectroscopic analyses. Cordyheptapeptide B (16) has an N-methyl-L-phenylalanine residue instead of the N-methyl-L-tyrosine in 15.
• Bioxanthracenes from the Insect Pathogenic Fungus Cordyceps pseudomilitaris BCC 1620. II. Structure Elucidation.
  作者：MASAHIKO ISAKA、PALANGPON KONGSAEREE、YODHATHAI THEBTARANONTH

  DOI：10.7164/antibiotics.54.36

  日期：——

  Structures of eleven bioxanthracenes (1-11) and two monomers (12 and 13), isolated from the insect pathogenic fungus Cordyceps pseudomilitaris BCC 1620, were elucidated. The structure, including the axial stereochemistry, of one of the major symmetrical dimers (1) was determined by X-ray crystallographic analysis, while the stereochemistries of the other isomers were deduced by chemical conversions and spectroscopic means.
• The first total synthesis of a bioxanthracene (−)-ES-242-4, an N-methyl-D-aspartate receptor antagonist
  作者：Kuniaki Tatsuta、Toru Yamazaki、Takanobu Mase、Takuji Yoshimoto

  DOI：10.1016/s0040-4039(98)00040-9

  日期：1998.3

  Bioxanthracene (-)-ES-242-4 has been synthesized from oxidative dimerization of a naphthopyran which was derived from an alpha,beta-unsaturated lactone and methyl 2,4-dimethoxy-6-methylbenzoate through tandem Michael-Dieckmann reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.