9-epoxyfalcarindiol | 1135133-70-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-epoxyfalcarindiol
• 英文别名: (3R,8R,9S,10R)-9,10-epoxy-heptadeca-1-en-4,6-diyn-3,8-diol；(1R,6R)-1-[(2S,3R)-3-heptyloxiran-2-yl]oct-7-en-2,4-diyne-1,6-diol
• CAS: 1135133-70-8
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: UJQVRPFUQYYCTH-VQHPVUNQSA-N

物化性质

• 沸点：
  432.2±45.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3R)-2,3-epoxy-1-decanol 在 Dimethylzinc 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 9-epoxyfalcarindiol
  参考文献：
  名称：

  Total syntheses of 9-epoxyfalcarindiol and its diastereomer

  摘要：

  The first total syntheses of 9-epoxyfalcarindiol la and its diastereomer lb have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)(4). (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.008

文献信息

• Polyacetylenes from Sardinian <i>Oenanthe fistulosa</i>: A Molecular Clue to <i>risus sardonicus</i>
  作者：Giovanni Appendino、Federica Pollastro、Luisella Verotta、Mauro Ballero、Adriana Romano、Paulina Wyrembek、Katarzyna Szczuraszek、Jerzy W. Mozrzymas、Orazio Taglialatela-Scafati

  DOI：10.1021/np8007717

  日期：2009.5.22

  An investigation of Oenanthe fistulosa from Sardinia afforded oenanthotoxin (1a) and dihydrooenanthotoxin (1b) from the roots and the diacetylenic epoxydiol 2 from the seeds. The absolute configuration of 1a and 1b was established as R by the modified Mosher's method, and the structure of 2 by chemical correlation with (+)-(3R,8S)-falcarindiol. Oenanthotoxin (1a) and dihydrooenanthotoxin (1b) were found to potently block GABAergic responses, providing a molecular rationale for the symptoms of poisoning from water-dropwort (Oenanthe crocata) and related plants. These observations bear relevance for a series of historical and ethnopharmacological observations on the identification of the Sardonic herb and the molecular details of the facial muscular contraction caused by its ingestion (risus sardonicus).
• Total syntheses of 9-epoxyfalcarindiol and its diastereomer
  作者：Yun Zhou、Yanli Huang、Shuoning Li、Pengfei Yang、Jiangchun Zhong、Jingwei Yin、Kaijie Ji、Yanqing Yang、Ning Ye、Lifeng Wang、Mingan Wang、Min Wang、Qinghua Bian

  DOI：10.1016/j.tetasy.2016.12.008

  日期：2017.2

  The first total syntheses of 9-epoxyfalcarindiol la and its diastereomer lb have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)(4). (C) 2017 Elsevier Ltd. All rights reserved.