1-adamantanemethanol tetrahydropyranyl ether | 1026255-88-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-adamantanemethanol tetrahydropyranyl ether
• 英文别名: 2-(1-Adamantylmethoxy)oxane
• CAS: 1026255-88-8
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: IASNDYVRJDSUDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-adamantanemethanol tetrahydropyranyl ether 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 5-(adamantan-1-yl-methoxy)-1-pentanol
  参考文献：
  名称：

  Process Development of a Potent Glucosylceramide Synthase Inhibitor

  摘要：

  An economic, scalable process for the production of glucosylceramide synthase (GCS) inhibitor 7 has been developed. Herein we report a three-step synthesis to aldehyde 4 with high yield and purity that employs the selective cleavage of an endocyclic C-O bond of a THP ether using borane/THF as the key step. This particular methodology has not been used previously from a development standpoint and offers an attractive way towards introducing pentanol side chains. Aldehyde 4 is then coupled with deoxynojirimycin via flow hydrogenation using an H-Cube to safely produce the free base of 7, which is isolated as an MSA salt in 50% overall yield. Herein we discuss the evolution of this process from its original form and the thermodynamics of its associated chemistry.

  DOI：

  10.1021/op2001222
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 1-金刚烷甲醇 在 hierarchical mesoporous beta zeolites nanoparticles 作用下， 生成 1-adamantanemethanol tetrahydropyranyl ether
  参考文献：
  名称：

  在浓反应混合物中作为醇四氢吡喃基化反应的催化剂获得的分层β沸石

  摘要：

  通过对浓缩的沸石凝胶前体（H 2）进行水热处理，可以得到由β纳米粒子（15 – 40 nm）组成的分层沸石。O / Si = 2.5 – 14），而无需使用复杂的SDA。所提出的方法是基于在特定的结晶条件下形成大量沸石核，随后它们的附聚导致颗粒的密集堆积，从而阻止了它们的进一步生长。十六烷基三甲基溴化铵（CTAB）的胶束可用于额外限制浓缩反应混合物的水热处理过程中沸石纳米颗粒的生长。这种结晶的减速促进了高度多孔的X射线无定形纳米铝硅酸盐的形成。由于中孔的发展和大分子对酸位的可及性增加，H-吡喃。

  DOI：

  10.1016/j.apcata.2019.117380

文献信息

• Process Development of a Potent Glucosylceramide Synthase Inhibitor
  作者：Christopher G.F. Cooper、Edward R. Lee、Richard A. Silva、André J. Bourque、Scott Clark、Sanjeev Katti、Vitaly Nivorozhkin

  DOI：10.1021/op2001222

  日期：2012.5.18

  An economic, scalable process for the production of glucosylceramide synthase (GCS) inhibitor 7 has been developed. Herein we report a three-step synthesis to aldehyde 4 with high yield and purity that employs the selective cleavage of an endocyclic C-O bond of a THP ether using borane/THF as the key step. This particular methodology has not been used previously from a development standpoint and offers an attractive way towards introducing pentanol side chains. Aldehyde 4 is then coupled with deoxynojirimycin via flow hydrogenation using an H-Cube to safely produce the free base of 7, which is isolated as an MSA salt in 50% overall yield. Herein we discuss the evolution of this process from its original form and the thermodynamics of its associated chemistry.
• Hierarchical Beta zeolites obtained in concentrated reaction mixtures as catalysts in tetrahydropyranylation of alcohols
  作者：Roman Barakov、Nataliya Shcherban、Pavel Yaremov、Igor Bezverkhyy、Valentina Tsyrina、Maksym Opanasenko

  DOI：10.1016/j.apcata.2019.117380

  日期：2020.3

  gel-precursor (H2O/Si = 2.5 – 14) without utilization of complex SDAs. The proposed approach is based on the formation of a large number of zeolite nuclei under particular crystallization conditions, followed by their agglomeration resulting in the dense packing of the particles preventing their further growth. The micelles of cetyltrimethylammonium bromide (CTAB) can be used to additionally limit the growth

  通过对浓缩的沸石凝胶前体（H 2）进行水热处理，可以得到由β纳米粒子（15 – 40 nm）组成的分层沸石。O / Si = 2.5 – 14），而无需使用复杂的SDA。所提出的方法是基于在特定的结晶条件下形成大量沸石核，随后它们的附聚导致颗粒的密集堆积，从而阻止了它们的进一步生长。十六烷基三甲基溴化铵（CTAB）的胶束可用于额外限制浓缩反应混合物的水热处理过程中沸石纳米颗粒的生长。这种结晶的减速促进了高度多孔的X射线无定形纳米铝硅酸盐的形成。由于中孔的发展和大分子对酸位的可及性增加，H-吡喃。