2-氰基-2-丙基戊酸乙酯 | 66546-90-5

• 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: 2-氰基-2-丙基戊酸乙酯
• 英文名称: ethyl 2-cyano-2-propylpentanoate
• 英文别名: 2-cyano-2-propyl-valeric acid ethyl ester；2-Cyan-2-propyl-valeriansaeure-aethylester；ethyl 2-cyano-2-propylvalerate；2,2-Dipropyl-cyanessigsaeure-ethylester
• CAS: 66546-90-5
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: CVMXOHNPQYTUOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-2-丙基戊酸乙酯 在 吗啉 、 2-羟基吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 N,N'-二环己基碳二亚胺 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 (E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-6,6-dipropyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone
  参考文献：
  名称：

  Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region)

  摘要：

  Analogs of the antitumor agents cryptophycins 1 and 8 with dialkyl substitution at C-6 (fragment C) were synthesized and evaluated for in vitro cytotoxicity against human leukemia cells (CCRF-CEM). The activity of these analogs decreased as the size of the substituents at C-6 increased. The C-6 spirocylopropyl compound (2g) was highly potent in vitro and showed excellent antitumor activity in animal models. (C) 1999 Elsevier Science Ltd. ALI rights reserved.

  DOI：

  10.1016/s0960-894x(98)00748-3
• 作为产物：
  描述：

  1-氯丙烷 、 氰乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 2-氰基-2-丙基戊酸乙酯
  参考文献：
  名称：

  基于丙戊酸类似物四唑衍生物的新型N-糖苷的合成

  摘要：

  合成了基于丙戊酸类似物四唑衍生物的新的N-糖苷。衍生自1，6-己二醇的双-四唑也连接至乙酰化葡萄糖并形成双-N-糖苷。使用FT IR，1 H和13 C NMR光谱进行了结构表征。

  DOI：

  10.1007/s13738-017-1055-7

文献信息

• THE SYNTHESIS AND ULTRAVIOLET SPECTRA OF SOME PYRAZOLONES
  作者：Paul E. Gagnon、Jean L. Boivin、Paul A. Boivin、R. Norman Jones

  DOI：10.1139/v51-023

  日期：1951.2.1

  phenylhydrazine and semicarbazide. 4-Benzyl-3-amino-1-phenyl-5-pyrazolone has been synthesized and its properties have been compared with those of the corresponding 2-phenylpyrazolone derivative. The ultraviolet absorption spectra of several pyrazolones have been determined.

  通过将单取代或双取代的氰基乙酸酯与肼、苯肼和氨基脲反应制备了 25 种吡唑啉酮。合成了 4-Benzyl-3-amino-1-phenyl-5-pyrazolone，并与相应的 2-phenylpyrazolone 衍生物进行了性能比较。已经测定了几种吡唑啉酮的紫外吸收光谱。
• Stereospecific and Stereoselective Reactions. V. Alkylation of Active Methylene Compounds by the Use of Alcohols, Diethyl Azodicarboxylate, and Triphenylphosphine
  作者：Toshio Kurihara、Masaru Sugizaki、Itaru Kime、Makoto Wada、Oyo Mitsunobu

  DOI：10.1246/bcsj.54.2107

  日期：1981.7

  alcohols and ethyl cyanoacetate (6) to give alkylated products in 30–80% yields. When ethyl acetoacetate, 1,3-cyclopentanedione, or 1,3-cyclohexanedione was used in place of 6, the corresponding O-alkylated products were obtained. The reaction of either (S)-(−)-ethyl lactate or (S)-(−)-ethyl 2-hydroxy-3-phenylpropionate with 1, 2, and 6, followed by hydrolysis resulted in the formation of (S)-(−)-methylsuccinic

  偶氮二甲酸二乙酯 (1) 和三苯基膦 (2) 反应形成的试剂与醇和氰乙酸乙酯 (6) 反应生成烷基化产物，收率 30-80%。当用乙酰乙酸乙酯、1,3-环戊二酮或1,3-环己二酮代替6时，得到相应的O-烷基化产物。(S)-(-)-乳酸乙酯或 (S)-(-)-2-羟基-3-苯基丙酸乙酯与 1、2 和 6 反应，然后水解形成 (S) -(-)-甲基琥珀酸或(S)-(-)-苄基琥珀酸。结果表明，在烷基化步骤中几乎完全反转了构型。
• STUDY OF 4-MONO- AND 4,4-DISUBSTITUTED-3-IMINO-2-BENZOYL-5-PYRAZOLONES
  作者：Paul E. Gagnon、Jean L. Boivin、Paul A. Boivin、Hugh M. Craig

  DOI：10.1139/v52-007

  日期：1952.1.1

  4-Mono- and 4,4-disubstituted-3-imino-2-benzoyl-5-pyrazolones have been prepared from the corresponding ethyl mono- or disubstituted cyanoacetates and N-benzoylhydrazine. The presence of the imino group in 4,4-disubstituted-3-imino-2-benzoyl-5-pyrazolones was ascertained by the hydrolysis of 4,4-dibenzyl-3-imino-2-benzoyl-5-pyrazolone into 4,4-dibenzyl-3-oxo-2-benzoyl-5-pyrazolone. In order to prove that the benzoyl group in these pyrazolones was not in Position 1, the synthesis of 4-benzyl-3-amino-1-benzoyl-5-pyrazolone was attempted from 4-benzyl-3-carbethoxy-1-benzoyl-5-pyrazolone through a Curtius degradation of the 3-carbethoxy substituent into a 3-amino group. It was found that the 1-benzoyl group was hydrolyzed at the same time as the 3-carbethoxyamino substituent. The ultraviolet absorption spectra of all these compounds are reported and discussed briefly.

  从相应的乙基单或双取代氰乙酸酯和N-苯甲酰肼制备了4-单取代和4,4-双取代-3-亚氨基-2-苯甲酰基-5-吡唑酮。通过将4,4-二苄基-3-亚氨基-2-苯甲酰基-5-吡唑酮水解为4,4-二苄基-3-酮基-2-苯甲酰基-5-吡唑酮，确定了4,4-双取代-3-亚氨基-2-苯甲酰基-5-吡唑酮中亚氨基基团的存在。为了证明这些吡唑酮中的苯甲酰基不在1位，尝试从4-苄基-3-羧乙酰氧基-1-苯甲酰基-5-吡唑酮通过卡蒂乌斯降解3-羧乙酰氧基取代基为3-氨基基团制备4-苄基-3-氨基-1-苯甲酰基-5-吡唑酮。结果发现，在3-羧乙酰氨基取代基水解的同时，1-苯甲酰基也被水解。报告并简要讨论了所有这些化合物的紫外吸收光谱。
• SYNTHESIS AND ULTRAVIOLET ABSORPTION OF SOME PYRAZOLONES
  作者：P. E. Gagnon、B. Nolin、R. N. Jones

  DOI：10.1139/v51-097

  日期：1951.10.1

  Thirteen 3-amino-5-pyrazolones substituted only in position 4 have been synthesized from the corresponding mono- or disubstituted cyanoacethydrazides or cyanoacetic esters in alkaline medium. Their ultraviolet light absorption spectra have been determined in neutral and acid solutions.

  已经从相应的单或双取代的氰乙酰肼或氰乙酸酯在碱性介质中合成了仅在4位取代的十三种3-氨基-5-吡唑酮。它们的紫外线吸收光谱已在中性和酸性溶液中确定。
• Process for the preparation of amino acid derivatives
  申请人：Degussa AG

  公开号：US06399809B1

  公开（公告）日：2002-06-04

  Process for the preparation of amino acid derivatives of the general formula I where R1-R4 are as defined herein, from the corresponding malonic acid monoester amides of the general formula II  by Hofmann degradation using a hypohalite in an aqueously basic medium, which comprises carrying out the reaction in the presence of an alcohol or amine and using the hypohalite in amounts of from 1.0 to 1.5 equivalents and the base in amounts of from 0.8 to 4.0 equivalents per mole of starting material II.

  本发明涉及一种制备一般式I中R1-R4如定义所示的氨基酸衍生物的过程，该过程从一般式II中对应的马隆酸单酯酰胺开始，通过在水性碱性介质中使用次卤酸进行Hofmann降解反应，其中在反应中存在醇或胺，并且使用1.0至1.5当量的次卤酸和0.8至4.0当量的碱每摩尔起始物II。