[3R,8R,9S,10S]-heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol | 1278462-00-2

• 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: [3R,8R,9S,10S]-heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol
• 英文别名: (3R,8R,9S,10S)-heptadec-1-ene-4,6-diyne-3,8,9,10-tetraol；(3R,8R,9S,10S)-heptadec-1-en-4,6-diyne-3,8,9,10-tetrol
• CAS: 1278462-00-2
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: MMVNLSXYHISWMN-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol 在 咪唑 、 甲醇 、 N-溴代丁二酰亚胺(NBS) 、 盐酸羟胺 、 对甲苯磺酸 、 silver nitrate 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.17h， 生成 [3R,8R,9S,10S]-heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol
  参考文献：
  名称：

  A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners

  摘要：

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.058

文献信息

• Enantioselective Synthesis of Possible Diastereomers of Heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol; Putative Structure of a Conjugated Diyne Natural Product Isolated from <i>Hydrocotyle leucocephala</i>
  作者：Kavirayani R. Prasad、Bandita Swain

  DOI：10.1021/jo102201k

  日期：2011.4.1

  Enantioselective synthesis of possible diastereomers of heptadeca-1-ene-4,6-diyne-3,8,9,10-tetrol, a structure proposed for the natural product isolated from Hydrocotyle leucocephala is accomplished. The reported spectral data of the natural product did not match those of any of the isomers that were synthesized and established that the structure proposed for the natural product is not correct and requires revision.
• A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners
  作者：Gullapalli Kumaraswamy、Kadivendi Sadaiah

  DOI：10.1016/j.tet.2011.10.058

  日期：2012.1

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.