2-methylene-3-methylsulfonyloxy-1-azabicyclo<2.2.2> octane | 135757-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 2-methylene-3-methylsulfonyloxy-1-azabicyclo<2.2.2> octane
• 英文别名: 2-Methylene-3-quinuclidinol mesylate；(2-methylidene-1-azabicyclo[2.2.2]octan-3-yl) methanesulfonate
• CAS: 135757-84-5
• 化学式: C₉H₁₅NO₃S
• 分子量: 217.289
• InChiKey: YGENKBIYCGLZLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylene-3-methylsulfonyloxy-1-azabicyclo<2.2.2> octane 在 lithium aluminium tetrahydride 、 叠氮化四丁基铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 2-aminomethyl-1-azabicyclo<2.2.2>oct-2-ene
  参考文献：
  名称：

  Kinetically-controlled displacement by azide on an allylic chloride: Synthesis of a highly potent serotonin-3 receptor ligand prototype

  摘要：

  The discovery and selective synthesis of a novel and highly potent serotonin-3 receptor ligand, 4-amino-5-chloro-2-methoxy-N-(1-azabicyclo[2.2.2]-oct-2-enyl-2-methyl) benzamide (4) are described. The key step in the preparation of 4 involves an unusual example of a kinetically controlled displacement to provide a thermodynamically disfavored allylic azide isomer. This azide is a precursor to 2-aminomethyl-1-azabicylo[2.2.2]oct-2-ene (5), a convergent intermediate for the synthesis of analogs related to 4.

  DOI：

  10.1016/s0040-4020(01)80973-x
• 作为产物：
  描述：

  2-methylenequinuclidin-3-one 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 2-methylene-3-methylsulfonyloxy-1-azabicyclo<2.2.2> octane
  参考文献：
  名称：

  Kinetically-controlled displacement by azide on an allylic chloride: Synthesis of a highly potent serotonin-3 receptor ligand prototype

  摘要：

  The discovery and selective synthesis of a novel and highly potent serotonin-3 receptor ligand, 4-amino-5-chloro-2-methoxy-N-(1-azabicyclo[2.2.2]-oct-2-enyl-2-methyl) benzamide (4) are described. The key step in the preparation of 4 involves an unusual example of a kinetically controlled displacement to provide a thermodynamically disfavored allylic azide isomer. This azide is a precursor to 2-aminomethyl-1-azabicylo[2.2.2]oct-2-ene (5), a convergent intermediate for the synthesis of analogs related to 4.

  DOI：

  10.1016/s0040-4020(01)80973-x

文献信息

• Azabicyclo amides and esters as 5-HT3 receptor antagonists
  申请人：Pfizer Inc.

  公开号：US05446050A1

  公开（公告）日：1995-08-29

  Novel azabicyclo amides and esters as antagonists at the 5-HT.sub.3 receptor and useful as anti-emetic agents.

  小说性质的杂环氨基酸酰胺和酯，作为5-HT.sub.3受体拮抗剂，可用作抗恶心剂。
• ROSEN, TERRY;GUARINO, KAREN J., TETRAHEDRON, 47,(1991) N9, C. 5391-5400
  作者：ROSEN, TERRY、GUARINO, KAREN J.

  DOI：——

  日期：——
• US5446050A
  申请人：——

  公开号：US5446050A

  公开（公告）日：1995-08-29
• [EN] AZABICYCLO AMIDES AND ESTERS AS 5-HT3 RECEPTOR ANTAGONISTS
  申请人：PFIZER INC.

  公开号：WO1991007402A1

  公开（公告）日：1991-05-30

  (EN) Novel azabicyclo amides and esters as antagonists at the 5-HT3 receptor and useful as anti-emetic agents.(FR) De nouveaux amides et esters azabicyliques antagonistes du récepteur de 5-HT3, utiles comme agents anti-émétiques.
• Kinetically-controlled displacement by azide on an allylic chloride: Synthesis of a highly potent serotonin-3 receptor ligand prototype
  作者：Terry Rosen、Karen J. Guarino

  DOI：10.1016/s0040-4020(01)80973-x

  日期：1991.7

  The discovery and selective synthesis of a novel and highly potent serotonin-3 receptor ligand, 4-amino-5-chloro-2-methoxy-N-(1-azabicyclo[2.2.2]-oct-2-enyl-2-methyl) benzamide (4) are described. The key step in the preparation of 4 involves an unusual example of a kinetically controlled displacement to provide a thermodynamically disfavored allylic azide isomer. This azide is a precursor to 2-aminomethyl-1-azabicylo[2.2.2]oct-2-ene (5), a convergent intermediate for the synthesis of analogs related to 4.