11-(methoxycarbonylamino)undecanoic acid | 176763-85-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-(methoxycarbonylamino)undecanoic acid
• CAS: 176763-85-2
• 化学式: C₁₃H₂₅NO₄
• 分子量: 259.346
• InChiKey: JUUIFNZSDRHDOE-UHFFFAOYSA-N

物化性质

• 沸点：
  414.9±18.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-(methoxycarbonylamino)undecanoic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以34%的产率得到11-氨基十一酸
  参考文献：
  名称：

  藜芦酸合成12-氨基十二烷酸和11-氨基十一烷酸

  摘要：

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.

  DOI：

  10.1007/s11746-997-0176-z
• 作为产物：
  描述：

  12-oxododecanoic acid 在 哌啶 、 sodium hydroxide 、 盐酸羟胺 、 溴 、 nickel diacetate 作用下， 以 甲醇 、 乙醇 、 xylene 为溶剂， 反应 24.42h， 生成 11-(methoxycarbonylamino)undecanoic acid
  参考文献：
  名称：

  藜芦酸合成12-氨基十二烷酸和11-氨基十一烷酸

  摘要：

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.

  DOI：

  10.1007/s11746-997-0176-z

文献信息

• Synthesis of nylon-11 monomer
  申请人：Howard University

  公开号：US05498733A1

  公开（公告）日：1996-03-12

  Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.

  Nylon-11单体，即11-氨基十一酸，是从12-氧代十二酸肟经过三步反应合成的，包括贝克曼重排反应，霍夫曼降解和水解。在镍醋酸四水合物存在下，醛肟酸被水解成11-碳酰胺基十一酸。然后，将这种酰胺基化合物在70℃至80℃的温度下与甲醇钠和溴反应，得到11-(甲氧羰基氨基)十一酸，再经过碱性水解和中和处理，最终得到11-氨基十一酸。
• OLIGOMERIC HINDERED AMINE LIGHT STABILIZERS BASED ON MULTI-FUNCTIONAL CARBONYL COMPOUNDS AND METHODS OF MAKING SAME
  申请人：Cytec Technology Corp.

  公开号：EP1360177A2

  公开（公告）日：2003-11-12
• US5498733A
  申请人：——

  公开号：US5498733A

  公开（公告）日：1996-03-12
• [EN] OLIGOMERIC HINDERED AMINE LIGHT STABILIZERS BASED ON MULTI-FUNCTIONAL CARBONYL COMPOUNDS AND METHODS OF MAKING SAME<br/>[FR] PHOTOSTABILISANTS OLIGOMERES A AMINES INHIBEES A BASE DE COMPOSES CARBONYLE MULTIFONCTIONNELS ET PROCEDES DE PRODUCTION DESDITS STABILISANTS
  申请人：CYTEC TECH CORP

  公开号：WO2002059090A2

  公开（公告）日：2002-08-01

  Oligomeric compounds and methods of making the compound having formula (II) wherein i, j, k, and l are integers from about 0 to 300 and the sum of i, j, k, and l is greater than 2, wherein the units F, F', and T are derived from one or more multi-functional carbonyl compounds of general structure (IV): DO-CO-CR?aRb-(-CRcRd-)¿n-NH-(Y)m-CO-OD wherein n is an integer from 1 to 15, m is either 0 or 1; Ra, Rb, R¿c¿, and Rd, are each a hydrogen or a hydrocarbyl group; Y is CO-(CReRf)p, wherein R?e and Rf¿ are each a hydrogen or hydrocarbyl group and p is zero or an integer from 1 to 20 or CO-C¿6?-H4-, wherein the substitution pattern on the phenylene group is an ortho, meta, or para substitution pattern, and one or more of the hydrogens of the phenylene group may be subtituted by a hydrocarbyl group or a functional group; and D is a hydrocarbyl group and the units E, E' and S are derived from one or more 1-substituted piperidin-4-ol or 4-aminopiperidines of general structure wherein Z is OH or NHG, wherein G is H or C1-C12 alkyl, R?1¿ is -(CH¿2?)s-OH, -(CH2)s-NH2, C1-C18 hydroxyalkoxy or C5-C12 hydroxycycloalkoxy; wherein s is an integer from 1 to 10; R?2¿ represents hydrogen, C¿1?-C8 alkyl, or benzyl; R?3, R4, R5, and R6¿ are each a hydrogen, C¿1?-C8 alkyl, benzyl or phenethyl, or two geminal R moieties, which together with the carbon to which they are attached form a C5-C10 cycloalkyl. The compounds are useful for stabilizing polymer compositions against photo- and thermal degradation.
• Syntheses of 12-aminododecanoic and 11-aminoundecanoic acids from vernolic acid
  作者：Folahan O. Ayorinde、Erick Y. Nana、Pete D. Nicely、Anthony S. Woods、Elvis O. Price、Chukwuma P. Nwaonicha

  DOI：10.1007/s11746-997-0176-z

  日期：1997.5

  Abstract12‐Aminododecanoic acid and 11‐aminoundecanoic acid, monomer precursors for nylon‐12 and nylon‐11, respectively, have been synthesized from vernolic (cis‐12,13‐epoxy‐cis‐9‐octadecenoic) acid via a reaction sequence that includes the formation of 12‐oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low‐temperature recrystallization at −20°C, gave 51% vernolic acid (97% purity, m.p. 23–25°C). Hydrogenation afforded cis‐12,13‐epoxystearic acid (m.p. 52–54°C, lit. m.p. 52–54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12‐oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12‐oxododecanoic acid oxime, which was catalytically reduced to give 12‐aminododecanoic acid with a yield greater than 85% and a melting point of 184–186°C (lit. m.p. 185–187°C). 11‐Aminoundecanoic acid was prepared from the 12‐oxododecanoic acid oxime via a three‐step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11‐carbamoylundecanoic acid (48% yield, m.p. 129–131°C, lit. m.p. 129–130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70–80°C to give 11‐(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84–86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11‐aminoundecanoic acid at 34% yield (m.p. 189–192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11‐(methoxycarbonylamino)undecanoic acid is provided.