1,6-di-((S)-oxiran-2-yl)-hexane | 161814-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 1,6-di-((S)-oxiran-2-yl)-hexane
• 英文别名: (1,2S:9S,10)-diepoxydecane；1,6-Di((S)-oxiran-2-yl)hexane；(2S)-2-[6-[(2S)-oxiran-2-yl]hexyl]oxirane
• CAS: 161814-90-0
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: CFHWRTNORXTUDE-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-di-((S)-oxiran-2-yl)-hexane 在 正丁基锂 、 dimethyl sulfide borane 、 水 、 sodium methylate 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium chloride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲醇 、 hexanes 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.58h， 生成 (R)-9-((5S)-2-oxo-tetrahydrofuran-5-yl)-non-1-en-3-ol
  参考文献：
  名称：

  Synthesis of the structures proposed for natural butanolides piliferolides A and C

  摘要：

  The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from D-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around delta 2.0 ppm was missing in the H-1 NMR data listing for the structures proposed for natural piliferolides, whereas the delta 29.7 ppm signal in the C-13 NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.037
• 作为产物：
  描述：

  (2S,9S)-Decane-1,2,9,10-tetraol 在 二正丁基氧化锡 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1,6-di-((S)-oxiran-2-yl)-hexane
  参考文献：
  名称：

  Synthesis of the structures proposed for natural butanolides piliferolides A and C

  摘要：

  The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from D-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around delta 2.0 ppm was missing in the H-1 NMR data listing for the structures proposed for natural piliferolides, whereas the delta 29.7 ppm signal in the C-13 NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.037

文献信息

• Absolute Configuration for 1,<i>n</i>-Glycols: A Nonempirical Approach to Long-Range Stereochemical Determination
  作者：Xiaoyong Li、Carmin E. Burrell、Richard J. Staples、Babak Borhan

  DOI：10.1021/ja2119767

  日期：2012.6.6

  n-glycols (n = 2-12, 16) bearing two chiral centers were rapidly determined via exciton-coupled circular dichroism (ECCD) using a tris(pentafluorophenyl)porphyrin (TPFP porphyrin) tweezer system in a nonempirical fashion devoid of chemical derivatization. A unique "side-on" approach of the porphyrin tweezer relative to the diol guest molecule is suggested as the mode of complexation.

  具有两个手性中心的 1,n-二醇 (n = 2-12, 16) 的绝对构型是通过激子耦合圆二色性 (ECCD) 使用三（五氟苯基）卟啉（TPFP 卟啉）镊子系统在非经验的情况下快速确定的没有化​​学衍生的时尚。卟啉镊子相对于二醇客体分子的独特“侧面”方法被建议作为络合模式。
• A Concise Enantiocontrolled Route to (+)-Patulolide C
  作者：Seiichi Takano、Taku Murakami、Kiyohiro Samizu、Kunio Ogasawara

  DOI：10.3987/com-94-s(b)47

  日期：——

  A naturally occurring antifungal macrolide (+)-patulolide C has been synthesized enantioselectively via the C-2-symmetric bis-epoxide by incorporation of two molecular units of (R)-0-benzylglycidol.
• Synthesis of the structures proposed for natural butanolides piliferolides A and C
  作者：Jing Guan、Zhi-Bin Zhen、Yang Zou、Zheng-Yu Yue、Ping Jiang、Yan Li、Yikang Wu

  DOI：10.1016/j.tet.2010.12.037

  日期：2011.2

  The structures proposed for natural butanolides piliferolides A and C have been synthesized. The allylic and lactone stereogenic centers in the target structures were derived from D-mannitol, while that near the side-chain terminal was taken from (R)-propylene oxide. The synthetic samples helped to reveal that a signal at around delta 2.0 ppm was missing in the H-1 NMR data listing for the structures proposed for natural piliferolides, whereas the delta 29.7 ppm signal in the C-13 NMR reported for the structure proposed for natural piliferolide C most likely stemmed from the impurities in the chromatography solvent. (C) 2011 Elsevier Ltd. All rights reserved.