5,5-亚乙二氧基己酸 | 5694-89-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5,5-亚乙二氧基己酸
• 英文名称: 5,5-ethylenedioxyhexanoic acid
• 英文别名: 4-(2-methyl-1,3-dioxolan-2-yl)butanoic acid
• CAS: 5694-89-3
• 化学式: C₈H₁₄O₄
• mdl: MFCD11554171
• 分子量: 174.197
• InChiKey: SDPLFVBOCUKIGE-UHFFFAOYSA-N

物化性质

• 沸点：
  291.6±15.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  5,5-亚乙二氧基己酸 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hexamethyldisilazane 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 对甲苯磺酸 、 臭氧 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 DL-脯氨酸 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 生成 ethyl (3S)-3-[[2-[(3S)-2-oxo-3-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]pyrrolidin-1-yl]acetyl]amino]-3-pyridin-3-ylpropanoate
  参考文献：
  名称：

  非肽alpha（v）beta（3）拮抗剂。第2部分：衍生自RGD三肽的受约束的缩水甘油酰胺。

  摘要：

  描述了RGD三肽的模拟物，它们是整联蛋白受体α（v）beta（3）的有效选择性拮抗剂。证明了使用5,6,7,8-四氢[1,8]萘啶基作为增强效价的N-末端。以前包含在alpha（IIb）beta（3）拮抗剂中的两个3-取代的-3-氨基丙酸被用来增强对目标受体的结合亲和力和功能活性。然后，通过使用环状缩水甘油酰胺键约束，进一步提高了亲和力。

  DOI：

  10.1016/s0960-894x(01)00687-4
• 作为产物：
  描述：

  4-(2-甲基-1,3-二氧杂烷-2-基)丁酸乙酯 在 盐酸 、 sodium hydroxide 作用下， 生成 5,5-亚乙二氧基己酸
  参考文献：
  名称：

  Three- and Four-Carbon Elongating Ring Expansion of Cyclic Acetals to Medium-Sized Dioxacycloalkenones. Use of the Intramolecular Formation of Oxonium Ylides

  摘要：

  The Rh(II)-catalyzed reaction of 2-(3'-diazo-2'-oxopropyl)-2-methyldioxolane (1) in the presence of a protic nucleophile (NuH) such as AcOH resulted in effective ring enlargement to give the 8-membered 3-acetoxydioxocanone 4a (41%) and dioxocan-2-en-1-one 3 (46%). Similar treatment of 2-(4'-diazo-3'-oxobutyl)-2-methyldioxolane (9) with AcOH gave 4-acetoxydioxonanone 10 (67%), which was readily hydrolyzed on silica gel to a tautomeric mixture of hydrolysis products 16a and 16b (total yield 46%). In contrast, similar treatment of 2-(5'-diazo-4'-oxopentyl)-2-methyldioxolane (19) gave 2,5-dioxa-1-methyldecalin-7-one (20, 24%), and the yield increased to 61% in the absence of AcOH, by Stevens rearrangement. The reaction of 1,3-dioxane homologues 26 and 31 gave similar results. All of these reactions can be explained in terms of the intermediacy of bicyclooxonium ylides, which undergo either a Stevens rearrangement or, after protonation by a NuH, ring enlargement through release of the strain of the bicyclic ylides. Evidence of the reversible formation of oxonium ylides is also provided.

  DOI：

  10.1021/jo961844x

文献信息

• Synthesis of 3D-Rich Heterocycles: Hexahydropyrazolo[1,5-<i>a</i>]pyridin-2(1<i>H</i>)-ones and Octahydro-2<i>H</i>-2a,2a¹-diazacyclopenta[<i>cd</i>]inden-2-ones
  作者：Eva Pušavec Kirar、Miha Drev、Jona Mirnik、Uroš Grošelj、Amalija Golobič、Georg Dahmann、Franc Požgan、Bogdan Štefane、Jurij Svete

  DOI：10.1021/acs.joc.6b01608

  日期：2016.10.7

  Grignard reagents followed by N-alkylation at position 1 afforded the 1,7,7-trisubstituted hexahydropyrazolo[1,5-a]pyridin-2(1H)-ones, whereas 1,3-dipolar cycloadditions of these dipoles to typical acetylenic and olefinic dipolarophiles gave 4a-substituted 2a,2a1-diazacyclopenta[cd]indene derivatives as the first representatives of a novel heterocyclic system. Regio- and stereoselectivity as well as the mechanism

  两个环状甲亚胺亚胺，7-甲基和7-苯基-2-氧代- Δ 7 -hexahydropyrazolo [1,5-一个]吡啶-8-鎓-1- IDE，在七个步骤制备来自各市售δ -酮酸。加入格氏试剂，然后在位置1进行N-烷基化，得到1,7,7-三取代的六氢吡唑并[1,5 - a ]吡啶2-2 （1 H）-一，而这些偶极的1,3-偶极环加成到典型的炔属和烯烃双极性亲和剂，得到4a-取代的2a，2a 1-二氮杂环戊基[ cd] indene衍生物作为新型杂环系统的第一个代表。使用计算和实验方法评估了区域和立体选择性以及这些[3 + 2]-环加成的机理。通过能量上有利的顺/内过渡态，获得的数据与极性一致的环加成机理相一致。
• Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C–N Bond Cleavage
  作者：Feba Thomas Pulikottil、Ramadevi Pilli、Rohith Valavil Suku、Ramesh Rasappan

  DOI：10.1021/acs.orglett.0c00554

  日期：2020.4.17

  The electrophile–electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C–N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional

  羧酸衍生物和烷基吡啶鎓盐通过C–N键断裂的亲电-亲电交叉偶联得到了发展。该方法以其简单性而著称，可指导我们选择各种功能化的酮，产率高至优异。除酰氯外，羧酸还用作酰化剂，这使我们能够结合酸敏感性官能团，例如MOM，BOC和乙缩醛。使用TEMPO进行的对照实验揭示了一个基本途径。
• Stereospecific total steroidal synthesis via substituted C/D-trans
  申请人：Hoffmann-La Roche Inc.

  公开号：US03950389A1

  公开（公告）日：1976-04-13

  Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##SPC1## Wherein m is an integer having a value of 1 or 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxymethylene CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is lower alkoxycarbonyl, aryloxy-carbonyl, lower cycloalkyloxycarbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.2 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitrobenzoyl, carboxy-lower alkanoyl, carboxybenzoyl, trifluoroacetyl and camphorsulfonyl And reacting them in the case where R.sub.8 and R.sub.9 taken together are methylene or R.sub.8 is hydrogen and R.sub.9 is methylene-X with .beta.-keto esters and other analogs of the formula ##EQU1## wherein R.sub. 6 is selected from the group CONSISTING OF ##EQU2## and LOWER ALKYL; R.sub.7 is lower alkyl; R.sub.15 is selected from the group consisting of oxo, lower alkylene-dioxy or (hydrogen and lower alkoxy); B is selected from the group consisting of lower alkoxy-carbonyl-methylene, lower-aryloxy-carbonyl-methylene, cyanomethylene, lower alkyl sulfinyl-methylene, lower alkyl sulfonyl-methylene, and R.sub.25 and R.sub.26 are independently selected from the group consisting of hydrogen, hydroxyl and lower alkyl.

  已知孕酮活性类固醇材料的全合成。这些类固醇可以根据所选的起始反应物进行合成，通过使用式子##SPC1##的双环化合物作为中间体。其中m是一个整数，取值为1或2；R.sub.4是氢或低烷基；Z是低烷基二氧甲基(CH(OR.sub.2))和羰基；当单独取R.sub.8时为氢；当单独取R.sub.9时为低烷氧羰基、芳基氧羰基、低环烷氧羰基、羰基卤化物、氢、羧基、甲酰和亚甲基-X，其中X是一个离去基团，当一起取时为亚甲基；但是当Z为羰基时，当单独取R.sub.8时为氢；当单独取R.sub.9时为羰基卤化物、氢、羧基、甲酰和亚甲基-X，其中X是一个离去基团，当一起取时为亚甲基；且当R.sub.8和R.sub.9一起取为亚甲基或R.sub.8为氢且R.sub.9为亚甲基-X时，与β-酮酯和其他类似物的式子##EQU1##反应，其中R.sub.6从群体中选择，包括##EQU2##和低烷基；R.sub.7是低烷基；R.sub.15从群体中选择，包括氧代、低烷基二氧或(氢和低烷氧)；B从群体中选择，包括低烷氧羰基亚甲基、低芳基氧羰基亚甲基、氰基亚甲基、低烷基亚磺酰基亚甲基、低烷基磺酰基亚甲基，R.sub.25和R.sub.26独立地从群体中选择，包括氢、羟基和低烷基。
• Stereospecific total steroidal synthesis via substituted c/d-trans
  申请人：Hoffmann-La Roche Inc.

  公开号：US03965117A1

  公开（公告）日：1976-06-22

  Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##SPC1## Wherein m is an integer having a value of 1 or 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is lower alkoxycarbonyl, aryloxy-carbonyl, lower cycloalkyloxycarbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.8 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.2 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitrobenzoyl, carboxy-lower alkanoyl, carboxybenzoyl, trifluoroacetyl and camphorsulfonyl.

  已知孕酮活性类固醇材料的全合成。可以根据所选择的特定起始反应物，通过使用公式## SPC1 ##的双环化合物作为中间体来合成类固醇，其中m是具有值为1或2的整数；R.sub.4是氢或较低的烷基；Z是较低的烷基二氧化物，CH（OR.sub.2）和羰基；当单独取R.sub.8时为氢；当单独取R.sub.9时为较低的烷氧羰基，芳基氧羰基，较低的环烷氧羰基，羰基卤化物，氢，羧基，甲酰和亚甲基-X，其中X是离去基团，当一起取时为亚甲基；但是当Z为羰基时，当单独取R.sub.8时为氢；当单独取R.sub.8时为羰基卤化物，氢，羧基，甲酰和亚甲基-X，其中X是离去基团，当一起取时为亚甲基；R.sub.2为氢，较低的烷基，较低的烷氧-较低的烷基，苯基-较低的烷基，四氢吡喃基，较低的烷酰基，苯甲酰基，硝基苯甲酰基，羧基-较低的烷酰基，羧基苯甲酰基，三氟乙酰基和香叶酸萜烷基。
• Process of synthesizing substituted indanones
  申请人：Hoffmann-La Roche Inc.

  公开号：US04048195A1

  公开（公告）日：1977-09-13

  Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##STR1## WHEREIN M IS AN INTEGER HAVING A VALUE OF 1 TO 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen, R.sub.9 when taken alone is lower alkoxy-carbonyl, aryloxy-carbonyl, lower cycloalkyloxy-carbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.2 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitrobenzoyl, carboxy-lower alkanoyl, carboxybenzoyl, trifluoroacetyl and camphorsulfonyl And reacting them in the case where R.sub.8 and R.sub.9 taken together are methylene or R.sub.8 is hydrogen and R.sub.9 is methylene-X with .alpha.-keto esters and other analogs of the formula ##STR2## wherein R.sub.6 is selected from the group ##STR3## lower alkyl; R.sub.7 is lower alkyl; R.sub.15 is selected from the group consisting of oxo, lower alkylene-dioxy or (hydrogen and lower alkoxy); B is selected from the group consisting of lower alkoxy-carbonylmethylene, lower-aryloxy-carbonyl-methylene, cyanomethylene, lower alkyl sulfinyl-methylene, lower alkyl sulfonyl-methylene, and R.sub.25 R.sub.26 are independently selected from the group consisting of hydrogen, hydroxyl and lower alkyl.

  已知孕激素活性类固醇材料的全合成。通过采用公式为##STR1##的双环化合物作为中间体，根据所选的特定起始反应物合成类固醇。其中，M是整数，取值为1至2；R.sub.4为氢或低碳基；Z为低碳基二氧、CH(OR.sub.2)和羰基；当R.sub.8单独取时，为氢；当R.sub.9单独取时，为低烷氧基羰基、芳氧基羰基、低环烷氧基羰基、羰基卤、氢、羧基、甲酰和亚甲基-X，其中X是离去基团；当一起取时，为亚甲基。但当Z为羰基时，当R.sub.8单独取时，为氢；当R.sub.9单独取时，为羰基卤、氢、羧基、甲酰和亚甲基-X，其中X是离去基团；当一起取时，为亚甲基；R.sub.2为氢、低碳基、低烷氧基-低碳基、苯基-低碳基、四氢吡喃基、低烷酰基、苯甲酰基、硝基苯甲酰基、羧基-低烷酰基、羧基苯甲酰基、三氟乙酰基和樟脑磺酰基。在R.sub.8和R.sub.9一起取为亚甲基或R.sub.8为氢且R.sub.9为亚甲基-X的情况下，与公式为##STR2##的α-酮酯和其他类似物反应。其中，R.sub.6选自##STR3##低碳基；R.sub.7为低碳基；R.sub.15选自羰基、低碳基二氧或（氢和低烷氧基）；B选自低烷氧基-羰基亚甲基、低-芳氧基-羰基亚甲基、氰基亚甲基、低碳基磺酰基亚甲基、低碳基磺酰基亚甲基和R.sub.25 R.sub.26独立选自氢、羟基和低碳基。