[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetate | 412271-86-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetate
• CAS: 412271-86-4
• 化学式: C₃₉H₄₁IO₁₀
• 分子量: 796.653
• InChiKey: ICTJNUKLXZURMF-WHJIUQFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetate 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以68%的产率得到[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-2-iodo-5-methoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

  摘要：

  Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00127-0
• 作为产物：
  描述：

  高香草酸 在 4-二甲氨基吡啶 、 硫酸 、 碘 、 silver trifluoroacetate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-acetyloxy-2-iodo-5-methoxyphenyl)acetate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor

  摘要：

  Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00127-0

文献信息

• Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor
  作者：Mark E. McDonnell、Sui-Po Zhang、Adrienne E. Dubin、Scott L. Dax

  DOI：10.1016/s0960-894x(02)00127-0

  日期：2002.4

  Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9.13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenlacetic acid ester of resiniferinol 5 displayed high affinity binding (K-i=0.71 nM) for the human vanilloid VR1 receptor and functioned as a partial agonist. (C) 2002 Elsevier Science Ltd. All rights reserved.