(+)-asperlin | 30387-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (+)-asperlin
• 英文别名: [(2R,3S)-2-[(2S,3R)-3-methyloxiran-2-yl]-6-oxo-2,3-dihydropyran-3-yl] acetate
• CAS: 30387-51-0
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: SPKNARKFCOPTSY-XWPZMVOTSA-N

物化性质

• 沸点：
  360.4±42.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  (+)-Acetylphomalactone 在 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(+)-asperlin
  参考文献：
  名称：

  Asymmetric total synthesis of (+)-phomalactone, (+)-acetylphomalactone and (+)-asperlin utilizing a novel syn-selective C4-oxa-vinylogous urethane

  摘要：

  The total synthesis of three natural products isolated from Nigrospora sp., Phoma sp., and Aspergillus nidulans(l) starting from an aldol reaction with a homochiral C-4-oxa-vinylogous urethane is described. Inherent stereoselectivity of the aldol reaction and overall alacrity of molecular construction are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02675-6

文献信息

• Stereocontrolled Synthesis of (±)-Asperlin and Related Stereoisomers Using Organotitanium Reagent
  作者：Hiroaki Hiraoka、Kyoji Furuta、Nobuo Ikeda、Hisashi Yamamoto

  DOI：10.1246/bcsj.57.2777

  日期：1984.10

  The naturally occurring antibiotics asperlin and related fungal metabolites containing a 5,6-dihydro-2-pyrone moiety have been synthesized stereoselectively. The propargyltitanium reagent derived from 1-trimethylsilyl-3-(tetrahydropyranyloxy)propyne condensed with crotonaldehyde affords the corresponding erythro alcohol as the major product, which is converted to (±)-asperlin and the related three stereoisomers in seven steps.

  天然存在的抗生素曲林及其含有5,6-二氢-2-吡喘部分的类似真菌代谢物已被立体选择性地合成。由1-三甲基硅基-3-（四氢吡喃氧基）丙炔衍生的炔基钛试剂与巴豆醛缩合，主要产物为赤型醇，经过七步反应转化为（±）-曲林及其相关的三个立体异构体。
• Total Synthesis of (+)-Asperlin Starting with (S,S)-Tartaric Acid
  作者：Yukio Masaki、Toshihiro Imaeda、Hirohisa Oda、Akichika Itoh、Motoo Shiro

  DOI：10.1246/cl.1992.1209

  日期：1992.7

  Natural (+)-asperlin was synthesized stereoselectively starting with (S,S)-tartaric acid by way of the 6,8-dioxabicyclo[3.2.1]octane skeleton.

  天然 (+)-asperlin 是由 (S,S)-酒石酸通过 6,8-二氧杂双环 [3.2.1] 辛烷骨架立体选择性合成的。
• A novel entry to naturally occurring 5-alkenyl α,β-unsaturated δ-lactones from d-glucose: syntheses of (+)-acetylphomalactone and (+)-asperlin
  作者：Ana M. Gómez、Beatriz López de Uralde、Serafín Valverde、J. Cristóbal López

  DOI：10.1039/a703561f

  日期：——

  A bicyclic pyranosidic glycoside 6, readily obtained from D-glucose, has been used as the key intermediate in enantioselective syntheses of (+)-acetylphomalactone and (+)-asperlin, in which the configuration at C-5 corresponds to that of the hexopyranosides in the L-sugar series.

  一种容易从 D-葡萄糖中获得的双环吡喃糖苷 6 已被用作对映体选择性合成 (+)-acetylphomalactone 和 (+)-asperlin 的关键中间体，其中 C-5 的构型与 L-糖系列中的六吡喃糖苷相对应。
• Syntheses of natural (+)-phomalactone, (+)-acetylphomalactone (+)-asperlin and their isomers.
  作者：Tetsuya MURAYAMA、Takeyoshi SUGIYAMA、Kyohei YAMASHITA

  DOI：10.1271/bbb1961.51.2055

  日期：——

  (+)-Phomalactone, (+)-acetylphomalactone, (+)-asperlin and their isomers were synthesized from 3-triethylsiloxypropyne and (S, E)-1-formyl-2-butenyl benzoate, which was easily prepared from (2R, 3S, E)-1, 2-cyclohexylidenedioxy-4-hexene-3-ol.

  (+)-Phomalactone, (+)-acetylphomalactone, (+)-asperlin 及其异构体由 3-三乙基硅氧丙炔和(S, E)-1-甲酰基-2-丁烯基苯甲酸酯合成，后者很容易由 (2R,3S,E)-1,2-环己基亚二氧基-4-己烯-3-醇制备。
• Peculiar Sharpless kinetic resolution of 2-furylmethanol and its application to the synthesis of (+)-Asperlin
  作者：Zhi-Cai Yang、Wei-Shan Zhou

  DOI：10.1016/0040-4039(95)01170-m

  日期：1995.7

  A peculiar kinetic resolution of E-1-(2-furyl)-2-buten-1-ol (1), which produced two oxidation products, pyranone (2) and epoxyalcohol (3), was developed by using the modified Sharpless reagents. A short synthesis of (+)-Asperlin was achieved starting from the optically active resolution products.

  利用改进的Sharpless试剂，开发了产生两种氧化产物吡喃酮（2）和环氧醇（3）的特殊的E-1-（2-呋喃基）-2-buten-1-ol（1）动力学拆分剂。 。从旋光拆分产物开始，短合成了（+）-Asperlin。