α-conidendrin monomethyl ether | 80287-36-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: α-conidendrin monomethyl ether
• 英文别名: Cycloarctigenin；(3aR,9S,9aR)-9-(3,4-dimethoxyphenyl)-7-hydroxy-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one
• CAS: 80287-36-1
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: HKRKRQPITZYXDQ-SIFCLUCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α-conidendrin monomethyl ether 在 乙醇 、 sodium ethanolate 作用下， 生成 β-conidendrin monomethyl ether
  参考文献：
  名称：

  Evaluation of Pulse-polio immunisation in rural area of Maharashtra

  摘要：

  An evaluation survey on Pulse-polio Immunisation (PPI) in January 2000 was carried out in rural areas of Maharashtra to assess the immunisation coverage, the knowledge regarding pulse-polio and the routine immunisation schedule. House-to-house survey was carried out and information was collected by interviewing the parents of 778 children. It was observed that PPI coverage was excellent i.e., 98%. Majority of informants were female. Knowledge about pulse-polio had a direct relationship with literacy. But knowledge regarding routine immunisation and the polio disease was not found satisfactory. Excellent coverage of pulse-polio Immunisation was found because of an organised and extensive campaign, use of mass media like T.V., radio, and home visits of peripheral health staff (as told by the informants). The distance of approach to a polio booth was less than a kilometre in almost all cases. Behaviour of health staff was satisfactory everywhere. The time-period required for getting vaccinated after arrival at the polio booth was less than 5 minutes. Thus it was a worthwhile attempt to evaluate PPI coverage is rural areas of Maharasthra. Excellent coverage of pulse-polio immunisation gives us the picture that poliomyelitis is on the verge of being eradicated from India, if the excellent coverage of PPI is followed by effective surveillence.

  DOI：

  10.1007/bf02762174
• 作为产物：
  描述：

  (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到α-conidendrin monomethyl ether
  参考文献：
  名称：

  木质素的自由基羧基化方法。（-）-香精素，（-）-苦参醇和相关天然产物的全合成。

  摘要：

  [反应：见正文]通过高度立体选择性的多米诺基自由基序列，提出了7种具有重要生物学意义的木脂素天然产物的总合成物，包括（-）-arctigenin，（-）-matairesinol和（-）-alpha-conidendrin。据报道，天然产物7-羟基arctigenin的立体化学是错误的。非对映异构结构被分配给天然产物。

  DOI：

  10.1021/ol049878b

文献信息

• Transformation of 2,3-dibenzylbutyrolactone lignans containing a secondary hydroxyl group to phenyltetralin lignans and their reduction products with lithium aluminum hydride.
  作者：SANSEI NISHIBE、HIROKI TSUKAMOTO、SUEO HISADA、SAKAE YAMANOUCHI、MICHIO TAKIDO

  DOI：10.1248/cpb.29.2082

  日期：——

  Two 2, 3-dibenzylbutyrolactone lignans containing a secondary hydroxyl group at one of the benzylic positions, 5-hydroxyarctigenin (I) and 5-hydroxytrachelogenin (XI), were transformed to phenyltetralin lignans, α-conidendrin monomethyl ether (II) and 3-hydroxy-α-conidendrin monomethyl ether (XII), respectively, by acid treatment. The hemiacetal lignan, (1S, 2R, 3S, 3aR) 6, 7-dimethoxy-3-hydroxy-2-hydroxymethyl-1-3', 4'-dimethoxyphenyl-1, 2, 3, 4-tetrahydronaphthalene-3-carboxylic acid lactol (XV), was obtained in addition to isoolivil dimethyl ether (XIV), the normal reduction product, when 3-hydroxy-α-conidendrin dimethyl ether (XIII) was treated with lithium aluminum hydride, and a mechanism is proposed for this reaction.

  两种2,3-二苄基丁内酯木脂素（其中一种苄基位置含有次级羟基，即5-羟基白屈菜素（I）和5-羟基白屈菜素（XI））在酸处理后分别转化为苯基四氢萘木脂素、α-香树精单甲醚（II）和3-羟基-α-香树精单甲醚（XII）。当3-羟基-α-香树精二甲醚（XIII）与氢化铝锂反应时，除了得到异欧李维醇二甲醚（XIV）这一正常还原产物外，还得到了半缩醛木脂素（1S,2R,3S,3aR）6,7-二甲氧基-3-羟基-2-羟甲基-1-3',4'-二甲氧基苯基-1,2,3,4-四氢萘-3-羧酸内酯（XV），并提出了该反应的机理。
• Omaki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1936, vol. 56, p. 985,990
  作者：Omaki

  DOI：——

  日期：——
• Evaluation of Pulse-polio immunisation in rural area of Maharashtra
  作者：S. V. Chincholikar、R. D. Prayag

  DOI：10.1007/bf02762174

  日期：2000.9

  An evaluation survey on Pulse-polio Immunisation (PPI) in January 2000 was carried out in rural areas of Maharashtra to assess the immunisation coverage, the knowledge regarding pulse-polio and the routine immunisation schedule. House-to-house survey was carried out and information was collected by interviewing the parents of 778 children. It was observed that PPI coverage was excellent i.e., 98%. Majority of informants were female. Knowledge about pulse-polio had a direct relationship with literacy. But knowledge regarding routine immunisation and the polio disease was not found satisfactory. Excellent coverage of pulse-polio Immunisation was found because of an organised and extensive campaign, use of mass media like T.V., radio, and home visits of peripheral health staff (as told by the informants). The distance of approach to a polio booth was less than a kilometre in almost all cases. Behaviour of health staff was satisfactory everywhere. The time-period required for getting vaccinated after arrival at the polio booth was less than 5 minutes. Thus it was a worthwhile attempt to evaluate PPI coverage is rural areas of Maharasthra. Excellent coverage of pulse-polio immunisation gives us the picture that poliomyelitis is on the verge of being eradicated from India, if the excellent coverage of PPI is followed by effective surveillence.
• Radical Carboxyarylation Approach to Lignans. Total Synthesis of (−)-Arctigenin, (−)-Matairesinol, and Related Natural Products
  作者：Joshua Fischer、Aaron J. Reynolds、Lisa A. Sharp、Michael S. Sherburn

  DOI：10.1021/ol049878b

  日期：2004.4.1

  of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)-alpha-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

  [反应：见正文]通过高度立体选择性的多米诺基自由基序列，提出了7种具有重要生物学意义的木脂素天然产物的总合成物，包括（-）-arctigenin，（-）-matairesinol和（-）-alpha-conidendrin。据报道，天然产物7-羟基arctigenin的立体化学是错误的。非对映异构结构被分配给天然产物。