(5aR,6R,9S,9aS)-3-(prop-2-yn-1-yloxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]dioxaphosphepine-3-oxide | 1289128-92-2

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: (5aR,6R,9S,9aS)-3-(prop-2-yn-1-yloxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]dioxaphosphepine-3-oxide
• 英文别名: (1R,2R,8S,9S)-5-prop-2-ynoxy-4,6-dioxa-5lambda5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide；(1R,2R,8S,9S)-5-prop-2-ynoxy-4,6-dioxa-5λ5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
• CAS: 1289128-92-2
• 化学式: C₁₂H₁₅O₄P
• 分子量: 254.222
• InChiKey: SYSXVHUBGGTQBB-FPOTVBLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5aR,6R,9S,9aS)-3-(prop-2-yn-1-yloxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]dioxaphosphepine-3-oxide 、 1-(叠氮甲基)-4-溴苯 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 14.0h， 以89%的产率得到(5aR,6R,9S,9aS)-3-((1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]-dioxaphosphepine-3-oxide
  参考文献：
  名称：

  “Click”-Capture, Ring-Opening Metathesis Polymerization (ROMP), Release: Facile Triazolation Utilizing ROMP-Derived Oligomeric Phosphates

  摘要：

  Soluble, high-load ring-opening metathesis polymerization (ROMP)-derived oligomeric triazole phosphates (OTP) are reported for application as efficient triazolating reagents of nucleophilic species. Utilizing a "Click"-capture, ROMP, release protocol, the efficient and purification-free, direct triazolation of N-, O-, and S-nucleophilic species was successfully achieved. A variety of OTP derivatives were rapidly synthesized as free-flowing solids on a multigram scale from commercially available materials.

  DOI：

  10.1021/ol200430c
• 作为产物：
  描述：

  5-norbornene-2,3-dimethanol 在 4-二甲氨基吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 (5aR,6R,9S,9aS)-3-(prop-2-yn-1-yloxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]dioxaphosphepine-3-oxide
  参考文献：
  名称：

  Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents

  摘要：

  The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nudeophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.

  DOI：

  10.1021/acs.joc.5b01456

文献信息

• US9029457B2
  申请人：——

  公开号：US9029457B2

  公开（公告）日：2015-05-12
• “Click”-Capture, Ring-Opening Metathesis Polymerization (ROMP), Release: Facile Triazolation Utilizing ROMP-Derived Oligomeric Phosphates
  作者：Toby R. Long、Saqib Faisal、Pradip K. Maity、Alan Rolfe、Ryan Kurtz、Sarra V. Klimberg、Muhammad-Rabbie Najjar、Fatima Z. Basha、Paul R. Hanson

  DOI：10.1021/ol200430c

  日期：2011.4.15

  Soluble, high-load ring-opening metathesis polymerization (ROMP)-derived oligomeric triazole phosphates (OTP) are reported for application as efficient triazolating reagents of nucleophilic species. Utilizing a "Click"-capture, ROMP, release protocol, the efficient and purification-free, direct triazolation of N-, O-, and S-nucleophilic species was successfully achieved. A variety of OTP derivatives were rapidly synthesized as free-flowing solids on a multigram scale from commercially available materials.
• Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents
  作者：Pradip K. Maity、Saqib Faisal、Alan Rolfe、Diana Stoianova、Paul R. Hanson

  DOI：10.1021/acs.joc.5b01456

  日期：2015.10.16

  The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nudeophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.