1,1-dimethoxy-2-methyl-pentan-3-one | 199728-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dimethoxy-2-methyl-pentan-3-one
• 英文别名: 2-methyl-3-oxo-valeraldehyde dimethylacetal；1,1-Dimethoxy-2-methyl-pentan-3-on；1,1-dimethoxy-2-methylpentan-3-one
• CAS: 199728-17-1
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: ZGDLRQHPLZUJIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1,1-dimethoxy-2-methyl-pentan-3-one 在 盐酸 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 溴 、 六正丁基二锡 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 73.17h， 生成 3,8,12,13,17,22-hexaethyl-2,7,8,23-tetramethyl-25,29-dioxasapphyrin
  参考文献：
  名称：

  Synthesis and Characterization of All-Alkyl-Substituted Mono-, Di-, and Trioxosapphyrins

  摘要：

  The synthesis and characterization of the following heterosapphyrins is presented: 3,7,18,22-tetraethyl-2,8,12,13,17,23-hexamethyl-27-oxasapphyrin (5), 3,8,12,13,17,22-hexaethyl-2,7,18,23-tetramethyl-15,29-dioxasapphyrin (6), and 3,7,18,22-tetraethyl-2,8,12,13,17,23-hexamethyl-15,27,29-trioxasapphyrin (7). These macrocycles were synthesized from the hitherto unknown precursors methyl 3,4-dimethylfuran-2-carboxylate (11) and methyl 4-ethyl-3-methylfuran-2-carboxylate (12). Single-crystal X-ray diffraction structures of the bis(hydrochloric acid) salt (5a) and the bis(trifluoroacetic acid) salt (5b) of 5 and of the bis(hydrochloric acid) salt (6a) of 6 were obtained. These structures are compared to those of the parent all-aza sapphyrin 4. In this context, we report the first solid-state structural analysis of a trifluoroacetic acid salt of sapphyrin (4b). Crystals of 5a are triclinic, space group P (1) over bar in a cell of the dimensions a = 11.9686(13) Angstrom, b = 12.790(2) Angstrom, c = 16.236(2) Angstrom, alpha = 80.924(10)degrees, beta = 88.845(9)degrees, gamma = 80.481(10)degrees, V = 2420.5(5) Angstrom(3), F(000) = 1036, rho = 1.38 g cm(3) with Z = 2. Crystals of 5b are monoclinic, space group P2(1)/c, in a cell of the dimensions a = 9.590(1) Angstrom, b = 33.911(3) Angstrom, c = 13.200(1) Angstrom, beta = 94.931(6)degrees, V = 4276.8(6) Angstrom(3), F(000)= 1904, rho = 1.42 g cm(3), with Z = 4. Crystals of 6a are triclinic, space group P (1) over bar, in a cell of the dimensions a = 12.827(3) Angstrom, b = 13.116(3) Angstrom, c = 17.202(7) Angstrom, alpha = 82.89(2)degrees, beta = 82.14(2)degrees, gamma = 80.22(1)degrees, V = 2810(2) Angstrom(3), F(000) = 1184, rho = 136 g cm(3), with Z = 2. Crystals of 4b are triclinic, space group P (1) over bar, in a cell of the dimensions a = 11.431(3) Angstrom, b = 11.563(2) Angstrom, c = 16.367(4) Angstrom, alpha = 88.07(2)degrees, beta = 75.25(2)degrees, gamma = 86.50(2), V = 2087.8(9) Angstrom(3), F(000)= 872, rho = 1.32, with Z = 2. The monooxasapphyrin salt 5a displays a structure very similar to that of the parent all-azasapphyrin (4a) in that one chloride anion is bound 1.936 Angstrom above and one chloride anion 1.814 Angstrom below the plane of the macrocycle. These distances are 1.774 and 1.877 Angstrom, respectively, for 4a. Almost the same behavior is found for 5b. Here, the carboxylate anions are bound 1.085 Angstrom above and 1.870 Angstrom below the plane of the macrocycle. These distances are 1.305 and 1.444 Angstrom, respectively, for 4b. Completely different behavior is observed in the case of 6a. In this instance, only one chloride anion is bound directly with a distance of 1.685 Angstrom above the plane of the macrocycle, while the other chloride anion is well removed from the dioxasapphyrin and solvated by four chloroform molecules.

  DOI：

  10.1021/jo9715736
• 作为产物：
  描述：

  甲酸甲酯 、 3-戊酮 在 乙醚 、 sodium methylate 作用下， 生成 1,1-dimethoxy-2-methyl-pentan-3-one
  参考文献：
  名称：

  Hydroxymethylene Ketones. I. The Preparation of β-Ketodimethylacetals and Methoxymethylene Ketones

  摘要：

  DOI：

  10.1021/ja01105a008

文献信息

• β-Keto Acetals. II. Synthesis of 3-Methyl- and 3-Phenyl-furans
  作者：D. M. BURNESS

  DOI：10.1021/jo01107a021

  日期：1956.1
• Hydroxymethylene Ketones. III. The Preparation of Methoxymethylene Ketones¹
  作者：E. Earl Royals、Kent C. Brannock

  DOI：10.1021/ja01640a062

  日期：1954.6
• [DE] GDH-MUTANTE MIT VERBESSERTER CHEMISCHER STABILITÄT<br/>[EN] GDH MUTANT HAVING IMPROVED CHEMICAL STABILITY<br/>[FR] GDH MUTANTE AYANT UNE STABILITÉ CHIMIQUE AMÉLIORÉE
  申请人：CONSORTIUM ELEKTROCHEM IND

  公开号：WO2006061137A1

  公开（公告）日：2006-06-15

  [EN] The invention relates to a glucose dehydrogenase having an amino acid sequence that corresponds to the amino acid sequence of a GDH of Bacillus subtilis comprising a glutamic acid group in position 96 with the exception that the glutamic acid group in position 96 is replaced by a nonpolar or hydrophobic amino acid or glycine.
  [FR] La présente invention concerne une glucose déshydrogénase ayant une séquence d'acides aminés qui correspond à la séquence d'acides aminés d'une GDH de Bacillus subtilis comprenant un radical acide glutamique en position 96, à la différence que le radical acide glutamique en position 96 est remplacé par une glycine ou un acide manié non polaire ou hydrophobe.
  [DE] Gegenstand der Erfindung ist Glucose Dehydrogenase mit einer Aminosäuresequenz die der Aminosäuresequenz einer GDH von Bacillus subtilis umfassend einen Glutaminsäurerest an Position 96 entspricht mit dem Unterschied, dass der Glutaminsäurerest an Position 96 gegen eine unpolare bzw. hydrophobe Aminosäure oder Glycin ausgetauscht ist.
• Hydroxymethylene Ketones. I. The Preparation of β-Ketodimethylacetals and Methoxymethylene Ketones
  作者：E. Earl Royals、Kent C. Brannock

  DOI：10.1021/ja01105a008

  日期：1953.5
• Synthesis and Characterization of All-Alkyl-Substituted Mono-, Di-, and Trioxosapphyrins
  作者：Jonathan L. Sessler、Michael C. Hoehner、Andreas Gebauer、Andrei Andrievsky、Vincent Lynch

  DOI：10.1021/jo9715736

  日期：1997.12.1

  The synthesis and characterization of the following heterosapphyrins is presented: 3,7,18,22-tetraethyl-2,8,12,13,17,23-hexamethyl-27-oxasapphyrin (5), 3,8,12,13,17,22-hexaethyl-2,7,18,23-tetramethyl-15,29-dioxasapphyrin (6), and 3,7,18,22-tetraethyl-2,8,12,13,17,23-hexamethyl-15,27,29-trioxasapphyrin (7). These macrocycles were synthesized from the hitherto unknown precursors methyl 3,4-dimethylfuran-2-carboxylate (11) and methyl 4-ethyl-3-methylfuran-2-carboxylate (12). Single-crystal X-ray diffraction structures of the bis(hydrochloric acid) salt (5a) and the bis(trifluoroacetic acid) salt (5b) of 5 and of the bis(hydrochloric acid) salt (6a) of 6 were obtained. These structures are compared to those of the parent all-aza sapphyrin 4. In this context, we report the first solid-state structural analysis of a trifluoroacetic acid salt of sapphyrin (4b). Crystals of 5a are triclinic, space group P (1) over bar in a cell of the dimensions a = 11.9686(13) Angstrom, b = 12.790(2) Angstrom, c = 16.236(2) Angstrom, alpha = 80.924(10)degrees, beta = 88.845(9)degrees, gamma = 80.481(10)degrees, V = 2420.5(5) Angstrom(3), F(000) = 1036, rho = 1.38 g cm(3) with Z = 2. Crystals of 5b are monoclinic, space group P2(1)/c, in a cell of the dimensions a = 9.590(1) Angstrom, b = 33.911(3) Angstrom, c = 13.200(1) Angstrom, beta = 94.931(6)degrees, V = 4276.8(6) Angstrom(3), F(000)= 1904, rho = 1.42 g cm(3), with Z = 4. Crystals of 6a are triclinic, space group P (1) over bar, in a cell of the dimensions a = 12.827(3) Angstrom, b = 13.116(3) Angstrom, c = 17.202(7) Angstrom, alpha = 82.89(2)degrees, beta = 82.14(2)degrees, gamma = 80.22(1)degrees, V = 2810(2) Angstrom(3), F(000) = 1184, rho = 136 g cm(3), with Z = 2. Crystals of 4b are triclinic, space group P (1) over bar, in a cell of the dimensions a = 11.431(3) Angstrom, b = 11.563(2) Angstrom, c = 16.367(4) Angstrom, alpha = 88.07(2)degrees, beta = 75.25(2)degrees, gamma = 86.50(2), V = 2087.8(9) Angstrom(3), F(000)= 872, rho = 1.32, with Z = 2. The monooxasapphyrin salt 5a displays a structure very similar to that of the parent all-azasapphyrin (4a) in that one chloride anion is bound 1.936 Angstrom above and one chloride anion 1.814 Angstrom below the plane of the macrocycle. These distances are 1.774 and 1.877 Angstrom, respectively, for 4a. Almost the same behavior is found for 5b. Here, the carboxylate anions are bound 1.085 Angstrom above and 1.870 Angstrom below the plane of the macrocycle. These distances are 1.305 and 1.444 Angstrom, respectively, for 4b. Completely different behavior is observed in the case of 6a. In this instance, only one chloride anion is bound directly with a distance of 1.685 Angstrom above the plane of the macrocycle, while the other chloride anion is well removed from the dioxasapphyrin and solvated by four chloroform molecules.