(+/-)-O-methylasparvenone | 136458-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-O-methylasparvenone
• 英文别名: 1(2H)-naphthalenone, 7-ethyl-3,4-dihydro-4,8-dihydroxy-6-methoxy-,(r)-；7-ethyl-4,8-dihydroxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 136458-96-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: NNATXEPYMGAPGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-dimethyl-propionic acid 5-hydroxy-7-methoxy-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 氢气 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， -30.0~50.0 ℃ 、101.33 kPa 条件下， 反应 4.75h， 生成 (+/-)-O-methylasparvenone
  参考文献：
  名称：

  Total Synthesis of 10-Norparvulenone and of O-Methylasparvenone Using a Xanthate-Mediated Free Radical Addition−Cyclization Sequence

  摘要：

  A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.

  DOI：

  10.1021/ol035394o

文献信息

• Regiospecific α-substitution of crotonic esters synthesis of naturally occurring derivatives of 6-ethyljuglone
  作者：Brigitte Caron、Paul Brassard

  DOI：10.1016/s0040-4020(01)87099-x

  日期：1991.1

  Methyl β-methoxycrotonate is alkylated regiospecifically, through the anion, in the α-position. Enolsilylation of the resulting β,γ-unsaturated ester affords the corresponding 1,1,2,3-tetrasubstituted butadiene. Cycloaddition of the latter to the appropriate halogenated benzoquinone, followed by various transformations, provides the first recorded syntheses of several natural products derived from

  β-甲氧基巴豆酸甲酯通过阴离子在α位上区域特异性地烷基化。所得β，γ-不饱和酯的烯醇化得到相应的1,1,2,3-四取代丁二烯。后者与适当的卤代苯醌进行环加成反应，然后进行各种转化，首次记录了衍生自6-乙基-7-甲氧基juglone的几种天然产物的合成。
• O-Methylasparvenone, a nitrogen-free serotonin antagonist
  作者：Michael Bös、Rolf Canesso、Noriko Inoue-Ohga、Atsuko Nakano、Yuki Takehana、Andrew J. Sleight

  DOI：10.1016/s0968-0896(97)00160-0

  日期：1997.12

  O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT2C ligands and found to be 5-HT2C antagonists. They represent the first nitrogen-free serotonin ligands. The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester. A short and efficient synthesis of rac-1 was developed. This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established. (C) 1997 Elsevier Science Ltd.
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.
• Total Synthesis of 10-Norparvulenone and of <i>O</i>-Methylasparvenone Using a Xanthate-Mediated Free Radical Addition−Cyclization Sequence
  作者：Alejandro Cordero Vargas、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol035394o

  日期：2003.10.1

  A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.