1,3-Diacetoxy-2-(acetoxymethyl)propane | 86629-63-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3-Diacetoxy-2-(acetoxymethyl)propane
• 英文别名: 2-hydroxymethyl-1,3-propanediol triacetate；1.3-Diacetoxy-2-acetoxymethyl-propan；1,3-Diactoxy-2-acetoxymethylpropan；triacetin；[3-Acetyloxy-2-(acetyloxymethyl)propyl] acetate
• CAS: 86629-63-2
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: NUOBYUPHBOMTDX-UHFFFAOYSA-N

物化性质

• 沸点：
  296.5±20.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-Diacetoxy-2-(acetoxymethyl)propane 在 咪唑 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 3-Acetoxy-2-(acetoxymethyl)-1-<(tert-butyldiphenylsilyl)oxy>propane
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039
• 作为产物：
  描述：

  [3-乙酰氧基-2-(乙酰氧基甲基)-2-硝基丙基]乙酸酯 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.0h， 以82%的产率得到1,3-Diacetoxy-2-(acetoxymethyl)propane
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039

文献信息

• 一种制备氨基醇衍生物的方法
  申请人：上海科技大学

  公开号：CN108707096B

  公开（公告）日：2021-03-19

  本发明提供了一种制备氨基醇衍生物的方法，其特征在于，包括对二元或多元醇羧酸酯的酯基进行取代反应，得到氨基醇衍生物，所述氨基醇衍生物中，氨基衍生为磺酰胺基，并至少保留一个羧酸酯基。本发明原料廉价易得，催化剂用量低，反应条件简单，产物选择性高。
• Reaktionen von Bleitetraacetat mit alicyclischen Alkoholen, III. Cyclopropyl- und Cyclobutylcarbinole. 18. Mitteilung über Reaktionen mit Bleitetraacetat
  作者：M. Lj. Mihailović、Ž. Čekovié

  DOI：10.1002/hlca.19690520429

  日期：——

  When treated with lead tetraacetate, cyclopropylcarbinol and cyclopropylmethylcarbinol do not give β-fragmentation products resulting from the intermediate formation of cyclopropyl radicals; however, cyclopropylmethylcarbinol affords a small amount of a fragmentation product which arises from CαCβ bond cleavage involving removal of a methyl radical. In contrast, cyclobutylcarbinol undergoes β-fragmentation

  当用四乙酸铅处理时，环丙基甲醇和环丙基甲基甲醇不会由于中间形成环丙基自由基而产生β片段化产物。然而，cyclopropylmethylcarbinol得到其来自℃的碎裂产物的少量α Ç β键断裂涉及甲基的去除。相反，环丁基甲醇以18％的收率经历β片段化反应，同时形成未重排的乙酸环丁酯和重排的乙酸环丙基甲基酯。这些结果表明，按以下顺序增加了自由基稳定性：环丙基<甲基<环丁基，而在环丁基甲醇的四乙酸铅反应中分离异构体的乙酸酯则进一步证明了在β片段化过程中，最初生成的碳自由基片段处于在最终产物形成之前，大部分被氧化为相应的碳离子。
• Novel 4-(2-furoyl) aminopiperidines, intermediates in synthesizing the same, process for producing the same and medicinal use of the same
  申请人：Fukutomi Ryuuta

  公开号：US20050085508A1

  公开（公告）日：2005-04-21

  There are provided novel 4-(2-furoyl)aminopiperidines represented by the general formula (I), their synthetic intermediates, processes for their preparation and medicaments containing them. In the above formula, X is CH or N, and Y is a group of the following general formula (II), formula (II-a) or formula (III): wherein a, b and c are each an integer of 0-6; Z is CH 2 or NH; W is O or S; T is O or N—R 15 wherein R 15 is H, a C1-C6 alkyl group, a benzyl group or a phenethyl group; and R 1 is H, a C1-C6 alkoxycarbonyl group, a benzyloxycarbonyl group, or the like. The 4-(2-furoyl)aminopiperidine derivatives according to this invention possess opioid μ antagonistic activity and are useful for the treatment or prevention of side effects which are caused by μ receptors agonist and which are selected from constipation, nausea/emesis or itch, or for the treatment or prevention of idiopathic constipation, postoperative ileus, paralytic ileus, irritable bowel syndrome or chronic pruritus.

  提供了一种新的4-(2-呋喃酰基)氨基哌啶化合物，其通式表示为(I)，以及它们的合成中间体、制备过程和含有它们的药物。 在上述式中，X为CH或N，Y为以下通式(II)、式(II-a)或式(III)的基团： 其中a、b和c均为0-6的整数；Z为CH2或NH；W为O或S；T为O或N—R15，其中R15为H、C1-C6烷基、苄基或苯乙基；R1为H、C1-C6烷氧羰基、苄氧羰基或类似基团。本发明所述的4-(2-呋喃酰基)氨基哌啶衍生物具有阿片μ受体拮抗活性，可用于治疗或预防由μ受体激动剂引起的副作用，包括便秘、恶心/呕吐或瘙痒，或用于治疗或预防特发性便秘、术后肠梗阻、麻痹性肠梗阻、肠易激综合征或慢性瘙痒。
• COMPOSITION, COMPOUND AND FILM FORMING METHOD
  申请人：Kawata Ken

  公开号：US20120201962A1

  公开（公告）日：2012-08-09

  A composition comprising at least one compound represented by the following formula (Z) is disclose. A-L-D 1 -(E) q -D 2 -(B) m —Z 1 —R} p (Z) In the formula, A represents a p-valent, linear or cyclic residue; L represents a single bond or a divalent linking group; p indicates an integer of at least 2; D 1 represents a carbonyl group (—C(═O)—) or a sulfonyl group (—S(═O) 2 —); D 2 represents a carbonyl group (—C(═O)—), a sulfonyl group (—S(═O) 2 —), a carboxyl group (—C(═O)O—), a sulfoxyl group (—S(═O) 2 O—), a carbamoyl group (—C(═O)N(Alk)-), or a sulfamoyl group (—S(═O) 2 N(Alk)-); E represents a divalent group; R represents a hydrogen atom, or a substituted or unsubstituted alkyl group having at most 7 carbon atoms; B represents oxyethylene group or the like; Z 1 represents a single bond, or a divalent group.

  本发明揭示了至少包含以下式子（Z）所表示的化合物的组合物。A-L-D1-(E)q-D2-(B)m—Z1—R}p(Z)在该式中，A表示p价的线性或环状残基；L表示单键或二价连接基团；p表示至少为2的整数；D1表示羰基（—C(═O)—）或磺酰基（—S(═O)2—）；D2表示羰基（—C(═O)—）、磺酰基（—S(═O)2—）、羧基（—C(═O)O—）、亚磺酰基（—S(═O)2O—）、氨基甲酰基（—C(═O)N(Alk)-）或磺酰胺基（—S(═O)2N(Alk)-）；E表示二价基团；R表示氢原子，或具有最多7个碳原子的取代或未取代的烷基；B表示氧乙烯基团或类似物；Z1表示单键或二价基团。
• COMPOUND
  申请人：FUJIFILM Corporation

  公开号：US20140012028A1

  公开（公告）日：2014-01-09

  A compound represented by following formula (I): A-L-D 1 -(E) q -D 2 -(B) m —Z 1 —R} p . In the formula, A represents a p-valent chain or cyclic residue; L represents a single bond or a divalent linking group; p represents an integer of 2 or more; D 1 represents a carbonyl group (—C(═O)—) or a sulfonyl group (—S(═O) 2 —); D 2 represents a carbonyl group (—C(═O)—), a sulfonyl group (—S(═O) 2 —), a carboxyl group (—C(═O)O—), a sulfonyloxyl group (—S(═O) 2 O—), a carbamoyl group (—C(═O)N(Alk)-) or a sulfamoyl group (—S(═O) 2 N(Alk)-); E represents a divalent group; and R represents a hydrogen atom, a substituted or non-substituted C 8 or longer alkyl group, a perfluoroalkyl group or a trialkylsilyl group.

  以下是公式（I）所代表的化合物：A-L-D1-(E)q-D2-(B)m—Z1—R}p。在此公式中，A代表一个p价链或环状残基；L代表单键或双价连接基团；p代表2或更多的整数；D1代表一个羰基（—C(═O)—）或磺酰基（—S(═O)2—）；D2代表一个羰基（—C(═O)—）、一个磺酰基（—S(═O)2—）、一个羧基（—C(═O)O—）、一个磺酰氧基（—S(═O)2O—）、一个氨基甲酰基（—C(═O)N(Alk)-）或一个磺酰氨基基团（—S(═O)2N(Alk)-）；E代表双价基团；R代表氢原子、取代或非取代的C8或更长的烷基团、全氟烷基团或三烷基硅基团。