(1R,2R,8S,9S)-5-chloro-4,6-dioxa-5lambda5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide | 1233656-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: (1R,2R,8S,9S)-5-chloro-4,6-dioxa-5lambda5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
• 英文别名: (1R,2R,8S,9S)-5-chloro-4,6-dioxa-5λ5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
• CAS: 1233656-16-0
• 化学式: C₉H₁₂ClO₃P
• 分子量: 234.619
• InChiKey: MODSIDNBXMIBSL-RGSKQIGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基苄醇 、 (1R,2R,8S,9S)-5-chloro-4,6-dioxa-5lambda5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide 在 NMI 作用下， 以 二氯甲烷 为溶剂， 生成 (5aR,6R,9S,9aS)-3-((3,5-dimethoxybenzyl)oxy)-1,5,5a,6,9,9a-hexahydro-6,9-methanobenzo[e][1,3,2]dioxaphosphepine 3-oxide
  参考文献：
  名称：

  ROMP-Derived Oligomeric Phosphates for Application in Facile Benzylation

  摘要：

  The development of new ROMP-based oligomeric benzyl phosphates (OBPn) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench-stable, pure white, free-flowing solids on multigram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported.

  DOI：

  10.1021/ol1006604
• 作为产物：
  描述：

  5-norbornene-2,3-dimethanol 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(1R,2R,8S,9S)-5-chloro-4,6-dioxa-5lambda5-phosphatricyclo[7.2.1.02,8]dodec-10-ene 5-oxide
  参考文献：
  名称：

  高载量，杂化二氧化硅固定的杂环磷酸苄基酯（Si–OHBP）和磷酸三唑基酯（Si–OHTP）烷基化试剂的合成

  摘要：

  报道了新的ROMP衍生的二氧化硅固定的杂环磷酸盐试剂的开发及其在无纯化方案中的应用。用功能化的Nb标签的杂环磷酸酯单体接枝降冰片烯降冰片烯官能化的（Nb标签）二氧化硅颗粒可有效产生高负载的杂化二氧化硅固定的低聚杂苄基磷酸酯（Si–OHBP）和杂三唑基磷酸酯（Si–OHTP）作为有效的烷基化反应代理商。这些试剂用于N-，O-和S-亲核物种多样化，有效进行杂苄基化和杂（三唑基）甲基化的应用已得到验证。

  DOI：

  10.1021/acscombsci.6b00042

文献信息

• “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.
• US9029457B2
  申请人：——

  公开号：US9029457B2

  公开（公告）日：2015-05-12
• US9556294B2
  申请人：——

  公开号：US9556294B2

  公开（公告）日：2017-01-31
• ROMP-Derived Oligomeric Phosphates for Application in Facile Benzylation
  作者：Toby R. Long、Pradip K. Maity、Thiwanka B. Samarakoon、Paul R. Hanson

  DOI：10.1021/ol1006604

  日期：2010.7.2

  The development of new ROMP-based oligomeric benzyl phosphates (OBPn) is reported for use as soluble, stable benzylating reagents. These oligomeric reagents are readily synthesized from commercially available materials and conveniently polymerized and purified in a one-pot process, affording bench-stable, pure white, free-flowing solids on multigram scale. Utilization in benzylation reactions with a variety of nucleophiles is reported.