3-methoxy-1H,3H-naphtho[1,8-cd]pyran-1-one | 31553-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methoxy-1H,3H-naphtho[1,8-cd]pyran-1-one
• 英文别名: 3-methoxy-3H-benzo[de]isochromen-1-one；8-Formyl-1-naphthoesaeure-methylester；Pseudomethyl-γ-formylnaphthoat；3-Methoxynaphthalid；4-Methoxy-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaen-2-one
• CAS: 31553-19-2
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: RTXMOUPTTNLYJZ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  421.8±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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-methoxy-1H,3H-naphtho[1,8-cd]pyran-1-one 在 1-环已基-2-吗啉乙基碳二亚胺对甲苯磺酸盐 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 zinc(II) chloride 作用下， 反应 0.25h， 生成 (3S)-4-cyclohexyl-2-hydroxy-3-<<(2S)-4-methyl-2-<<(2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionyl>amino>pentanoyl>amino>butyric acid isopropyl ester
  参考文献：
  名称：

  New modified heterocyclic phenylalanine derivatives. Incorporation into potent inhibitors of human renin

  摘要：

  Modified heterocyclic phenylalanine analogues designed as replacements for the P3-P4 region were synthesized and incorporated into renin inhibitors. These inhibitors were found to have significant activity versus human recombinant renin, as well as in vivo activity. The compounds proved to be very resistant to chymotrypsin degradation, as exemplified by compound 8, which remained greater than 60% intact after a 24-h exposure to chymotrypsin. In contrast, the Boc-Phe analogue was nearly completely degraded after 1 h. Compound 6 proved to be the most potent renin inhibitor with an IC50 = 8.9 nM. These stable cyclized phenylalanines should prove to be generally useful as a substitute for Boc-Phe in protease inhibitors.

  DOI：

  10.1021/jm00083a005
• 作为产物：
  描述：

  1-hydroperoxy-3-methoxy-1H,3H-naphtho(1.8-cd)pyran 在 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到3-methoxy-1H,3H-naphtho[1,8-cd]pyran-1-one
  参考文献：
  名称：

  New approaches to the synthesis of spiro-peroxylactones

  摘要：

  三氟乙醇中（烯丙二氧）环十二烷过氧化氢的臭氧分解反应得到了相应α-过氧化氢和α-羟基取代的螺-四氧杂环烷混合物，其环大小范围为7至12。过氧化氢的脱水或羟基化合物的氧化反应生成了相应的过氧化环酸。1,2,6,7-四氧杂螺[7.11]十九烷-3-酮的固态结构通过X射线晶体学分析确定。

  DOI：

  10.1039/b300342f

文献信息

• Synthetic Photochemistry. XVIII. A Sensitizer Dependence in the Photooxidation of Indene and Acenaphthylene. The Occurrence of<i>cis</i>-1,2-Glycol Formation in a Rose Bengal-sensitized Reaction
  作者：Toshihide Hatsui、Hitoshi Takeshita

  DOI：10.1246/bcsj.53.2655

  日期：1980.9

  Upon Rose Bengal-sensitized photooxygenation, indene and acenaphthylene afforded substantial amounts of the expected cis-glycols by means of the reduction of the intermediate dioxetanes. The formerly proposed structure of one of the isomeric methoxy hydroperoxides was revised on the basis of the chemical and spectral evidence.

  在玫瑰红敏化光氧合作用下，茚和苊通过中间二氧杂环丁烷的还原作用生成了大量预期的顺式乙二醇。根据化学和光谱证据，对以前提出的其中一种异构体甲氧基过氧化氢的结构进行了修改。
• Preparation of α-aminophosphines on solid support: model studies and parallel synthesis
  作者：B. Bar-Nir Ben-Aroya、Moshe Portnoy

  DOI：10.1016/s0040-4020(02)00471-4

  日期：2002.6
• HATSUI TOSHIHIDE; TAKESHITA HITOSHI, BULL. CHEM. SOC. JAP., 1980, 53, NO 9, 2655-2658
  作者：HATSUI TOSHIHIDE、 TAKESHITA HITOSHI

  DOI：——

  日期：——
• New approaches to the synthesis of spiro-peroxylactones
  作者：Kevin J. McCullough、Hidekazu Tokuhara、Araki Masuyama、Masatomo Nojima

  DOI：10.1039/b300342f

  日期：2003.4.23

  Ozonolysis of (alkenyldioxy)cyclododecyl hydroperoxides in trifluoroethanol gave a separable mixture of the corresponding α-hydroperoxy- and α-hydroxy-substituted spiro-tetraoxacycloalkanes with ring sizes in the range 7–12. Dehydration of the hydroperoxides or oxidation of the hydroxy-compounds afforded the corresponding peroxylactones. The solid-state structure of 1,2,6,7-tetraoxaspiro[7.11]nonadecan-3-one was determined by X-ray crystallographic analysis.

  三氟乙醇中（烯丙二氧）环十二烷过氧化氢的臭氧分解反应得到了相应α-过氧化氢和α-羟基取代的螺-四氧杂环烷混合物，其环大小范围为7至12。过氧化氢的脱水或羟基化合物的氧化反应生成了相应的过氧化环酸。1,2,6,7-四氧杂螺[7.11]十九烷-3-酮的固态结构通过X射线晶体学分析确定。
• New modified heterocyclic phenylalanine derivatives. Incorporation into potent inhibitors of human renin
  作者：Timothy D. Ocain、David D. Deininger、Ralph Russo、Nancie A. Senko、Alan Katz、Jan M. Kitzen、Robert Mitchell、George Oshiro、Anthony Russo

  DOI：10.1021/jm00083a005

  日期：1992.3

  Modified heterocyclic phenylalanine analogues designed as replacements for the P3-P4 region were synthesized and incorporated into renin inhibitors. These inhibitors were found to have significant activity versus human recombinant renin, as well as in vivo activity. The compounds proved to be very resistant to chymotrypsin degradation, as exemplified by compound 8, which remained greater than 60% intact after a 24-h exposure to chymotrypsin. In contrast, the Boc-Phe analogue was nearly completely degraded after 1 h. Compound 6 proved to be the most potent renin inhibitor with an IC50 = 8.9 nM. These stable cyclized phenylalanines should prove to be generally useful as a substitute for Boc-Phe in protease inhibitors.