9-oxaheptadecane-1,17-diol | 217439-18-4

• 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-oxaheptadecane-1,17-diol
• 英文别名: 8,8'-oxybis(octan-1-ol)；8-(8-Hydroxyoctoxy)octan-1-ol
• CAS: 217439-18-4
• 化学式: C₁₆H₃₄O₃
• 分子量: 274.444
• InChiKey: ZVPQCQLXVMUJNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-oxaheptadecane-1,17-diol 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 31.5h， 生成 17-hydroxy-9-oxaheptadec-1-yl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside
  参考文献：
  名称：

  Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study

  摘要：

  Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.

  DOI：

  10.1021/jo400095u
• 作为产物：
  描述：

  1,8-辛二醇 在 palladium 10% on activated carbon 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.5h， 生成 9-oxaheptadecane-1,17-diol
  参考文献：
  名称：

  Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study

  摘要：

  Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.

  DOI：

  10.1021/jo400095u

文献信息

• Selective Macrocycle Formation in Cavitands
  作者：Ji-Min Yang、Yang Yu、Julius Rebek

  DOI：10.1021/jacs.0c12302

  日期：2021.2.10

  unfavorable entropy of macrocyclic closure allows undesired intermolecular reactions to compete. Here, we apply cavitands to the selective intramolecular aldol/dehydration reaction of long-chain α,ω-dialdehydes in aqueous solution. Hydrophobic forces drive the dialdehydes into the cavitands in folded conformations and favor macrocyclization reactions over intermolecular reactions observed in bulk solution

  长链线性前体的传统端到端环化是困难的，并且通常是不可预测的，因为大环封闭的不利熵使得不希望的分子间反应竞争。在这里，我们将cavitands用于水溶液中长链α，ω-二醛的选择性分子内羟醛/脱水反应。疏水力将二醛以折叠的构型驱入腔体中，并且比在本体溶液中观察到的分子间反应更有利于大环化反应。大范围的醛醇缩合反应产物在很宽的范围（11至17元环）上以良好的收率（30-85％）被分离出来。与传统模板在其组装主机中成为访客不同，
• US4008294A
  申请人：——

  公开号：US4008294A

  公开（公告）日：1977-02-15
• WO2023/89158
  申请人：——

  公开号：——

  公开（公告）日：——
• Surface-Tethered Iterative Carbohydrate Synthesis: A Spacer Study
  作者：N. Vijaya Ganesh、Kohki Fujikawa、Yih Horng Tan、Swati S. Nigudkar、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/jo400095u

  日期：2013.7.19

  Comparative study of Surface-Tethered Iterative Carbohydrate Synthesis (STICS) using HPLC-assisted experimental setup clearly demonstrates benefits of using longer spacer-anchoring systems. The use of mixed self-assembled monolayers helps provide the required space for glycosylation reaction around the immobilized glycosyl acceptor. Both extension of the spacer length and using mixed self-assembled monolayers help promote the reaction, and the beneficial effects may include moving the glycosyl acceptor further out into solution and providing additional conformational flexibility. It is possible that surface-immobilized glycosyl acceptors with a longer spacer (C8-O-C8)-lipoic acid have a higher tendency to mimic a solution-phase reaction environment than acceptors with shorter spacers.