6-(nitrooxy)-hexanal | 197585-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(nitrooxy)-hexanal
• 英文别名: 6-Oxohexyl nitrate
• CAS: 197585-99-2
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: BSOUFWBHIRXMPX-UHFFFAOYSA-N

物化性质

• 沸点：
  239.9±23.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-氯-2,4-二磺酰胺基苯胺 、 6-(nitrooxy)-hexanal 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以41%的产率得到2H-1,2,4-benzothiadiazine-7-sulfonamide-6-chloro-3,4-dihydro-3-[5-(nitrooxy)pentyl]-1,1-dioxide
  参考文献：
  名称：

  Nitric oxide enhancing diuretic compounds, compositions and methods of use

  摘要：

  该发明描述了包含至少一种增强一氧化氮利尿化合物或其药用盐的新型组合物和试剂盒，以及可选地，至少一种增强一氧化氮化合物和/或至少一种治疗剂的试剂盒。该发明还提供了以下方法：(a)治疗由过多水分和/或电解贮留引起的症状；(b)治疗心血管疾病；(c)治疗肾血管疾病；(d)治疗糖尿病；(e)治疗由氧化应激引起的疾病；(f)治疗内皮功能障碍；(g)治疗由内皮功能障碍引起的疾病；(h)治疗肝硬化；(j)治疗子痫前期；(k)治疗骨质疏松症；(l)治疗肾病；(m)治疗外周血管疾病；(n)治疗门静脉高压；(o)治疗中枢神经系统疾病；(p)治疗代谢综合征；(q)治疗性功能障碍；以及(r)高脂血症。增强一氧化氮利尿化合物包括至少一种增强一氧化氮基团，通过碳、氧和/或氮等一个或多个位点与利尿化合物连接，连接通过不能水解的键或基团。

  公开号：

  US20060189603A1
• 作为产物：
  描述：

  6-hydroxyhexyl nitrate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以100%的产率得到6-(nitrooxy)-hexanal
  参考文献：
  名称：

  Nitric oxide enhancing diuretic compounds, compositions and methods of use

  摘要：

  该发明描述了包含至少一种增强一氧化氮利尿化合物或其药用盐的新型组合物和试剂盒，以及可选地，至少一种增强一氧化氮化合物和/或至少一种治疗剂的试剂盒。该发明还提供了以下方法：(a)治疗由过多水分和/或电解贮留引起的症状；(b)治疗心血管疾病；(c)治疗肾血管疾病；(d)治疗糖尿病；(e)治疗由氧化应激引起的疾病；(f)治疗内皮功能障碍；(g)治疗由内皮功能障碍引起的疾病；(h)治疗肝硬化；(j)治疗子痫前期；(k)治疗骨质疏松症；(l)治疗肾病；(m)治疗外周血管疾病；(n)治疗门静脉高压；(o)治疗中枢神经系统疾病；(p)治疗代谢综合征；(q)治疗性功能障碍；以及(r)高脂血症。增强一氧化氮利尿化合物包括至少一种增强一氧化氮基团，通过碳、氧和/或氮等一个或多个位点与利尿化合物连接，连接通过不能水解的键或基团。

  公开号：

  US20060189603A1

文献信息

• [EN] PROCESS FOR THE PREPARATION OF A NITRIC OXIDE DONATING PROSTAGLANDIN ANALOGUE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN ANALOGUE DE PROSTAGLANDINE DONNEUR D'OXYDE NITRIQUE
  申请人：NICOX SA

  公开号：WO2019162149A1

  公开（公告）日：2019-08-29

  The present invention relates to a process for preparing the hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]- 3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The 6-(nitrooxy)hexanoyl chloride intermediate is prepared by ring-opening reaction of 2-caprolactone and subsequent nitration of the 6-hydroxyhexanoic acid potassium salt with a mixture of HNO3 and H2SO4 in dichloromethane.

  本发明涉及一种制备式(I)的己酸6-(硝基氧)-,(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(乙基氨基)-7-氧代-2-庚烯-1-基]-3,5-二羟基环戊基]-1-(2-苯乙基)-2-丙烯-1-基酯的方法。根据本发明，化合物(I)可以通过将硼酸保护的比马前列素与6-(硝基氧)己酰氯偶联并去除硼酸保护基来高效纯净地制备。6-(硝基氧)己酰氯中间体通过2-己内酯的开环反应和随后在二氯甲烷中使用HNO3和H2SO4混合物对6-羟基己酸钾盐进行硝化制备。
• <b>Products of the Gas-Phase Reaction of OH </b><b>Radicals with Cyclohexane:  Reactions of the </b><b>Cyclohexoxy Radical</b>
  作者：Sara M. Aschmann、Andrew A. Chew、Janet Arey、Roger Atkinson

  DOI：10.1021/jp971869f

  日期：1997.10.1

  Products of the gas-phase reactions of OH radicals with cyclohexane and cyclohexane-d(12) in the presence of NO have been investigated using gas chromatography with flame ionization detection, combined gas chromatography-mass spectrometry, and in situ direct air-sampling atmospheric pressure ionization tandem mass spectrometry (API-MS). Cyclohexanone and cyclohexyl nitrate (and their deuterated analogues) were identified and quantified, with formation yields of cyclohexanone and cyclohexyl nitrate from the cyclohexane reaction of 0.321 +/- 0.035 and 0.165 +/- 0.021, respectively, and with cyclohexanone-d(10) and cyclohexyl nitrate d(11) formation yields from the cyclohexane-d(12) reaction of 0.156 +/- 0.017 and 0.210 +/- 0.025, respectively. The remaining products must arise from the decomposition and/or isomerization reactions of the intermediate cyclohexoxy radical. API-MS analyses of the cyclohexane and cyclohexane-d(12) reactions showed the formation of cyclohexanone and cyclohexyl nitrate (and their deuterated analogues), together with ion peaks attributed to HC(O)CH2CH2CH2CH2CH2ONO2 (formed from NO addition to the HC(O)CH2CH2CH2CH2CH2OO. radical formed after decomposition of the cyclohexoxy radical) and HC(O)CH2CH(OH)CH2CH2CHO (formed after isomerization of the HC(O)CH2CH2CH2CH2CH2O. radical). No evidence for isomerization of the cyclohexoxy radical was obtained from the API-MS analyses. The reactions of the cyclohexoxy radical are discussed and the data extended to the reactions of the cyclopentoxy and cycloheptoxy radicals formed from cyclopentane and cycloheptane.
• PROCESS FOR THE PREPARATION OF A NITRIC OXIDE DONATING PROSTAGLANDIN ANALOGUE
  申请人：Nicox S.A.

  公开号：EP3530649B1

  公开（公告）日：2020-09-30
• Nitric oxide enhancing diuretic compounds, compositions and methods of use
  申请人：Garvey S. David

  公开号：US20060189603A1

  公开（公告）日：2006-08-24

  The invention describes novel compositions and kits comprising at least one nitric oxide enhancing diuretic compound, or pharmaceutically acceptable salts thereof, and, optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating conditions resulting from excessive water and/or electrolyte retention; (b) treating cardiovascular diseases; (c) treating renovascular diseases; (d) treating diabetes; (e) treating diseases resulting from oxidative stress; (f) treating endothelial dysfunctions; (g) treating diseases caused by endothelial dysfunctions; (h) treating cirrhosis; (j) treating pre-eclampsia; (k) treating osteoporosis; (l) treating nephropathy; (m) treating peripheral vascular diseases; (n) treating portal hypertension; (o) treating central nervous system disorders; (p) treating metabolic syndrome; (q) treating sexual dysfunctions; and (r) hyperlipidemia. The nitric oxide enhancing diuretic compounds comprise at least one nitric oxide enhancing group linked to the diuretic compound through one or more sites such as carbon, oxygen and/or nitrogen via a bond or moiety that cannot be hydrolyzed.

  该发明描述了包含至少一种增强一氧化氮利尿化合物或其药用盐的新型组合物和试剂盒，以及可选地，至少一种增强一氧化氮化合物和/或至少一种治疗剂的试剂盒。该发明还提供了以下方法：(a)治疗由过多水分和/或电解贮留引起的症状；(b)治疗心血管疾病；(c)治疗肾血管疾病；(d)治疗糖尿病；(e)治疗由氧化应激引起的疾病；(f)治疗内皮功能障碍；(g)治疗由内皮功能障碍引起的疾病；(h)治疗肝硬化；(j)治疗子痫前期；(k)治疗骨质疏松症；(l)治疗肾病；(m)治疗外周血管疾病；(n)治疗门静脉高压；(o)治疗中枢神经系统疾病；(p)治疗代谢综合征；(q)治疗性功能障碍；以及(r)高脂血症。增强一氧化氮利尿化合物包括至少一种增强一氧化氮基团，通过碳、氧和/或氮等一个或多个位点与利尿化合物连接，连接通过不能水解的键或基团。