(Z)-16,16-二甲氧基-7-十六碳烯 | 71393-90-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (Z)-16,16-二甲氧基-7-十六碳烯
• 英文名称: 9-cis-hexadecenal dimethyl acetal
• 英文别名: 7-Hexadecene, 16,16-dimethoxy-, (7Z)-；(Z)-16,16-dimethoxyhexadec-7-ene
• CAS: 71393-90-3
• 化学式: C₁₈H₃₆O₂
• 分子量: 284.483
• InChiKey: HPVRSOHMDHUDAZ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-16,16-二甲氧基-7-十六碳烯 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 (Z)-9-十六碳烯醛
  参考文献：
  名称：

  [EN] PROCESS FOR BORANE-MEDIATED ESTER REDUCTION
  [FR] PROCÉDÉ DE RÉDUCTION D'ESTER À MÉDIATION PAR BORANE

  摘要：

  Methods for preparation of aldehydes from carboxylic acid esters, including unsaturated fatty acid esters and triacyl glycerides, are described. The methods include combining an ester with a silane reagent and a borane catalyst to form a mixed silyl acetal which is hydrolyzed to provide the aldehyde product. The reagents are combined in a controlled manner to limit the generation of heat and hydrogen gas. New procedures for hydrolysis of acetal intermediates and improved purification and recovery processes provide aldehyde products in excellent yield.

  公开号：

  WO2023114437A1
• 作为产物：
  描述：

  8-溴-1,1-二甲氧基辛烷 在 Pd-BaSO₄ 喹啉 、 正丁基锂 、 氢气 作用下， 以 甲醇 为溶剂， 4.0~25.0 ℃ 、101.33 kPa 条件下， 反应 2.58h， 生成 (Z)-16,16-二甲氧基-7-十六碳烯
  参考文献：
  名称：

  Darmstoff analogs. 3. Actions of choline esters of acetal phosphatidic acids on visceral smooth muscle

  摘要：

  A number of naturally occurring phospholipids, e.g. the acetal phosphatidic acid derivatives that comprise Darmstoff (1) and the phosphatidylcholine derivative platelet activating factor (PAF), cause contraction of certain visceral smooth muscles and cause platelet activation. Because the Darmstoff phosphatidic acids and PAF are structurally similar, it was of interest to compare the biological actions of choline esters of Darmstoff with those of PAF and of the parent Darmstoff phosphatidic acids. To this end, [(2-pentadecyl-1,3-dioxolan-4-yl)methyl]phosphocholine (3a), [[2-(cis-8-heptadecenyl)-1,3-dioxolan-4-yl]methyl]phosphocho line (3b), and [[2-(cis-8-pentadecenyl)-1,3-dioxolan-4-yl]methyl]phosphocho line (3c) were synthesized. Compounds 3a, 3b, 3c, and PAF caused dose-dependent relaxation of taenia coli strips. In contrast, the unesterified materials 1a and 1b, as well as lyso-PAF, caused contraction in taenia coli strips. Thus, the contractile effect of Darmstoff is reversed on esterification with choline. In preparations of whole trachea, both 1a and 3a had contractile effects similar to those of PAF.

  DOI：

  10.1021/jm00126a029

文献信息

• MARX, MICHAEL H.;WILEY, ROBERT A.;SATCHELL, D. G.;MAGUIRE, M. HELEN, J. MED. CHEM., 32,(1989) N, C. 1319-1322
  作者：MARX, MICHAEL H.、WILEY, ROBERT A.、SATCHELL, D. G.、MAGUIRE, M. HELEN

  DOI：——

  日期：——
• Darmstoff analogs. 3. Actions of choline esters of acetal phosphatidic acids on visceral smooth muscle
  作者：Michael H. Marx、Robert A. Wiley、D. G. Satchell、M. Helen Maguire

  DOI：10.1021/jm00126a029

  日期：1989.6

  A number of naturally occurring phospholipids, e.g. the acetal phosphatidic acid derivatives that comprise Darmstoff (1) and the phosphatidylcholine derivative platelet activating factor (PAF), cause contraction of certain visceral smooth muscles and cause platelet activation. Because the Darmstoff phosphatidic acids and PAF are structurally similar, it was of interest to compare the biological actions of choline esters of Darmstoff with those of PAF and of the parent Darmstoff phosphatidic acids. To this end, [(2-pentadecyl-1,3-dioxolan-4-yl)methyl]phosphocholine (3a), [[2-(cis-8-heptadecenyl)-1,3-dioxolan-4-yl]methyl]phosphocho line (3b), and [[2-(cis-8-pentadecenyl)-1,3-dioxolan-4-yl]methyl]phosphocho line (3c) were synthesized. Compounds 3a, 3b, 3c, and PAF caused dose-dependent relaxation of taenia coli strips. In contrast, the unesterified materials 1a and 1b, as well as lyso-PAF, caused contraction in taenia coli strips. Thus, the contractile effect of Darmstoff is reversed on esterification with choline. In preparations of whole trachea, both 1a and 3a had contractile effects similar to those of PAF.
• [EN] PROCESS FOR BORANE-MEDIATED ESTER REDUCTION<br/>[FR] PROCÉDÉ DE RÉDUCTION D'ESTER À MÉDIATION PAR BORANE
  申请人：[en]PROVIVI, INC.

  公开号：WO2023114437A1

  公开（公告）日：2023-06-22

  Methods for preparation of aldehydes from carboxylic acid esters, including unsaturated fatty acid esters and triacyl glycerides, are described. The methods include combining an ester with a silane reagent and a borane catalyst to form a mixed silyl acetal which is hydrolyzed to provide the aldehyde product. The reagents are combined in a controlled manner to limit the generation of heat and hydrogen gas. New procedures for hydrolysis of acetal intermediates and improved purification and recovery processes provide aldehyde products in excellent yield.