(9R,10S)-9,10-二氢-9-羟基-10-甲氧基-8,8-二甲基-2H,8H-苯并[1,2-B:3,4-B']二吡喃-2-酮 | 23733-92-8

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: (9R,10S)-9,10-二氢-9-羟基-10-甲氧基-8,8-二甲基-2H,8H-苯并[1,2-B:3,4-B']二吡喃-2-酮
• 英文名称: (9R,10S)-9-hydroxy-10-methoxy-8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one
• 英文别名: (-)-trans-(3'R,4'S)-methylkhellactone；trans-4'-O-methylkhellactone；(-)-trans-methylkhellactone；(9R)-9r-hydroxy-10t-methoxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-one；(9R)-9r-Hydroxy-10t-methoxy-8,8-dimethyl-9,10-dihydro-8H-pyrano[2,3-f]chromen-2-on；3'(S)-Hydroxy-4'(S)-methoxydihydrosuelin；trans-Methylkhellactone；(9R,10S)-9-hydroxy-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-f]chromen-2-one
• CAS: 23733-92-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: MDDPVXHWOABQJQ-UONOGXRCSA-N

物化性质

• 熔点：
  161-162℃
• 沸点：
  414.6±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+)-沙米丁 在 1,4-二氧六环 、 盐酸 、 氢氧化钾 作用下， 生成 (9R,10S)-9,10-二氢-9-羟基-10-甲氧基-8,8-二甲基-2H,8H-苯并[1,2-B:3,4-B']二吡喃-2-酮
  参考文献：
  名称：

  Schroeder et al., Chemische Berichte, 1959, vol. 92, p. 2338,2362

  摘要：

  DOI：

文献信息

• A Concise Route for the Synthesis of Biologically Interesting Pyranocoumarins - Seselin, (±)-<i>cis</i>-Khellactone, (±)-Quianhucoumarin D, and the (±)-5-Deoxyprotobruceol-I Regioisomer
  作者：Yong Rok Lee、Won Kyong Lee、Seok Kyun Noh、Won Seok Lyoo

  DOI：10.1055/s-2006-926329

  日期：——

  An efficient synthesis of pyranocoumarins is achieved starting from 2H-pyrans. This process provides naturally occurring seselin, cis-khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer.

  高效合成吡喃香豆素的过程是以2H-吡喃为起始材料。该过程提供了天然存在的塞斯林、顺式凯拉克酮、奇安胡香豆素D以及5-去氧原白头翁素I的区位异构体。
• Coumarins from the Fruits of <i>Seseli </i><i>d</i><i>evenyense</i>
  作者：Jarek Widelski、Eleni Melliou、Nikolas Fokialakis、Prokopios Magiatis、Kazimierz Glowniak、Ioanna Chinou

  DOI：10.1021/np050209w

  日期：2005.11.1

  Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4' (5) and 3' (6) as well as the 2'S epimer of 8-(2

  从芝麻雪茄西蒙凯（Seseli devenyense Simonkai）的果实中分离出八种新的香豆素。它们的结构由NMR和质量数据确定，其绝对构型由化学降解相关反应确定。新结构是（+）-lomatin（3，4）的癸酸酯和十二酸酯，在位置4'（5）和3'（6）的（+）-顺式-甲壳酮的癸酸酯以及2'S差向异构体名为devenyol的8-（2,3-二羟基-3-甲基丁基）-7-羟基chromen-2-one（7），其在3'和7位的两个O-单葡糖苷分别称为devenyosides A（8）和B（9） ，以及名为devenyoside C（10）的相应3'-和7-O-二葡萄糖苷。鉴于is科的其他成员仅产生化合物7-9的2'R差向异构体，因此该植物是基于生物多样性的立体化学多样性的一个有趣实例。
• Schmid, Scientific Proceedings of the Royal Dublin Society, 1956, vol. 27, p. 145,150, 151
  作者：Schmid

  DOI：——

  日期：——
• Phytotoxic Compounds from <i>Prionosciadium </i><i>w</i><i>atsoni</i>
  作者：Norma Valencia-Islas、Hamed Abbas、Robert Bye、Rubén Toscano、Rachel Mata

  DOI：10.1021/np010448t

  日期：2002.6.1

  Bioassay-guided fractionation of a phytotoxic extract of Prionosciadium watsoni led to the isolation of three new pyranocoumarins and two pyranochromones. The new compounds were characterized as propionic acid (9R,10R)-9-acetoxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one-10-yl ester (1), isobutyric acid (9R,10R)-9-hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one-10-yl ester (2), isobutyric acid (9R)-8,8-dimethyl-9,10-dihydro-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one-9-yl ester (10), 2-methylbut-(2Z)-enoic acid (3R)-5-methoxy-3,4-dihydro-2,2,8-trimethyl-6-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-3-yl ester (11), and isobutyric acid (3R)-5-methoxy-3,4-dihydro2,2,8-trimethyl-6-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-3-yl ester (12) by spectroscopic and chemical methods. The stereochemistry at the stereogenic centers was established by applying the Mosher ester methodology. The structures of 1 and 2 were corroborated by single-crystal X-ray diffraction studies. The phytotoxic activity of the isolated compounds was assessed on Amaranthus hypochondriacus, Echinochloa crus-galli, and Lemna pausicostata. The phytotoxins also modified the electrophoretic mobility of calmodulin from both bovine-brain and spinach.
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 3. The “Libraries from Libraries” Principle for Diversity Enhancement of Benzopyran Libraries
  作者：K. C. Nicolaou、J. A. Pfefferkorn、S. Barluenga、H. J. Mitchell、A. J. Roecker、G.-Q. Cao

  DOI：10.1021/ja0020355

  日期：2000.10.1

  As described in the preceding two papers, our interest in the construction of natural and natural product-like libraries for chemical biology studies led to the development of a new solid-phase cycloloading strategy for the construction of substituted benzopyrans. Herein, we report a parallel solution-phase method that facilitates the enhancement of both the size and diversity of these non-oligomeric benzopyran libraries using the "libraries from libraries" principle. We examine the rationale behind the use of this tandem strategy to construct discrete small molecule libraries, and describe the development of a polymer-assisted solution-phase (PASP) methodology necessary to effect the required transformations. Once developed, this chemistry is applied to two demonstration libraries.