jatamansinol | 19380-05-3

• 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
• 英文名称: jatamansinol
• 英文别名: (+)-lomatin；lomatin；Lonatin；2H,8H-Benzo[1,2-b:3,4-b']dipyran-2-one, 9,10-dihydro-9-hydroxy-8,8-dimethyl-, (R)-；(9R)-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
• CAS: 19380-05-3
• 化学式: C₁₄H₁₄O₄
• mdl: MFCD00600449
• 分子量: 246.263
• InChiKey: UJSHBYQGQRPVNO-LLVKDONJSA-N

物化性质

• 保留指数：
  2365;2365;2365

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  jatamansinol 在 吡啶 作用下， 反应 2.0h， 生成 3′,4′-di-O-acetyl-cis-khellactone
  参考文献：
  名称：

  药用食品。XX。来自当归北川当归根的Vasorelaxant活性成分：Hyuganins A，B，C和D的结构。

  摘要：

  从北川当归获得的具有血管舒张活性的甲醇提取物中，分离出四种新的内酯类香豆素，hyuganins A，B，C和D，以及十二种已知的香豆素，两种已知的炔属化合物和一种已知的木脂素。Hyuganins A，B，C和D的结构是根据化学和物理化学证据确定的。九种主要香豆素（hyuganin A，异常蛋白，pteryxin，isopteryxin，isoepoxypteryxin，praerosides II和IV，apiosylskimmin，（R）-peucedanol 7-O-beta-D-glucopyranoside），两种炔属化合物[（--falcarinol和falcarinol）研究了相关化合物对高浓度K +（High K +）-和dl-去甲肾上腺素（NE）诱导的收缩的抑制活性。结果表明3'-和4' 酸内酯型香豆素的β-酰基对于High K +对收缩的抑制活性至关重要。Hyuganin

  DOI：

  10.1248/cpb.48.1429
• 作为产物：
  描述：

  奥斯生诺 在 Oxone 、 Shi's ketone 、 四丁基硫酸氢铵 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 二甲醇缩甲醛 、 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 jatamansinol
  参考文献：
  名称：

  通过O-甲硅烷基保护的邻烯丙基苯酚的对映选择性环氧化不对称合成2-取代的二氢苯并呋喃和3-羟基二氢苯并吡喃

  摘要：

  的施型环氧化ø -叔丁基二苯基硅烷基（TBDPS）保护ø -allylphenols作为有效的策略来构建二氢苯并呋喃和dihydrobenzopyrans在高达97％的ee值。这种方法导致了（+）的对映选择性合成- marmesin，（ - ） - （3' - [R）-decursinol，和（+） - lomatin。

  DOI：

  10.1002/adsc.201000505

文献信息

• 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。
• Coumarin sulphates of Seseli libanotis
  作者：John Lemmich、Marawan Shabana

  DOI：10.1016/s0031-9422(00)85044-x

  日期：1984.4

  Abstract Three new sulphate ester salts derived from known coumarin alcohols–one of them tertiary–have been obtained from roots of Seseli libanotis subsp. eu-libanotis . Their structures were established as (2′ S )-rutaretin-1″-sulphate, (3′ R )-lomatin-3′-sulphate and (3′ R ,4′ R )-khellactone-3′-sulphate. They were together with their parent alcohols characterized by 13 C NMR spectroscopy. It is

  摘要 从 Seseli libanotis subsp. 的根中获得了三种源自已知香豆素醇的新硫酸酯盐 - 其中一种是叔醇。eu-libanotis . 它们的结构被确定为 (2' S )-rutaretin-1"-sulphate, (3' R )-lomatin-3'-sulphate 和 (3' R ,4' R )-khellactone-3'-sulphate。它们与通过 13 C NMR 光谱表征的母体醇一起。这是关于植物中香豆素硫酸盐的第一份报告。
• Semisynthesis of Ingenol 3-Angelate (PEP005): Efficient Stereoconservative Angeloylation of Alcohols
  作者：Xifu Liang、Gunnar Grue-Sørensen、Anders Petersen、Thomas Högberg

  DOI：10.1055/s-0032-1317415

  日期：——

  A high-yielding method was developed for the preparation of ingenol 3-angelate (PEP005, ingenol mebutate) via the corresponding 5,20-acetonide without concomitant isomerization of the angelate (Z-form) to the corresponding tiglate (E-form). The general scope of the stereoconservative esterification method was further evaluated on several different alcohols, giving the angelates in up to quantitative yield without isomerization to the tiglate.
• 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.
• The absolute configuration of angular 3′-acyloxypyranocoumarins by vibrational circular dichroism exciton chirality
  作者：Abigail I. Buendía-Trujillo、J. Martín Torrres-Valencia、Pedro Joseph-Nathan、Eleuterio Burgueño-Tapia

  DOI：10.1016/j.tetasy.2014.09.001

  日期：2014.10

  A complex mixture of lomatin C-3' esters and (-)-O-angeloyllomatin 1 was isolated from the seeds of Prionosciadium thapsoides. Since a literature search revealed that some lomatin C-3' monoesters have positive specific rotations, while others had negative values, the absolute configuration of all of the molecules was determined to be (R) by exciton chirality in the infrared region, and by chemical correlation. A single crystal X-ray study of acetyllomatin 3, using the Flack and Hooft parameters, independently confirmed this absolute configuration. (C) 2014 Elsevier Ltd. All rights reserved.