N-<(allyloxy)carbonyl>cysteamine | 135920-21-7

• 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: N-<(allyloxy)carbonyl>cysteamine
• 英文别名: allyl (2-mercaptoethyl)carbamate；N-allyloxycarbonylcysteamine；Allyl(2-mercaptoethyl)carbamate；prop-2-enyl N-(2-sulfanylethyl)carbamate
• CAS: 135920-21-7
• 化学式: C₆H₁₁NO₂S
• 分子量: 161.225
• InChiKey: RKSVIUBDQWRRHX-UHFFFAOYSA-N

物化性质

• 沸点：
  258.5±33.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-<(allyloxy)carbonyl>cysteamine 在 氢氧化钾 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 生成 (5R,6S)-3-(2-Allyloxycarbonylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
  参考文献：
  名称：

  外消旋2-（烷硫基）-6-（1-羟乙基）青霉烯的合成; 尝试通过铜（I）合成Penem-促进环化

  摘要：

  描述了由常见的单环氮杂环丁酮前体的非对映异构体6-（1-羟乙基）-2-乙硫基和2-（2-氨基乙硫基）-penem-3-羧酸酯的立体控制合成。铜（I）促进合适的N / C-3 secopenems的环化反应可产生“ isopenems”（7-氧代-2-thia-1-azabicyc10o [3.2.0]-庚-3-烯）作为唯一的双环产品。

  DOI：

  10.1016/s0040-4039(01)81939-0
• 作为产物：
  描述：

  烯丙基琥珀酰亚胺基碳酸酯 、 巯基乙胺 在 氢氧化钾 作用下， 生成 N-<(allyloxy)carbonyl>cysteamine
  参考文献：
  名称：

  外消旋2-（烷硫基）-6-（1-羟乙基）青霉烯的合成; 尝试通过铜（I）合成Penem-促进环化

  摘要：

  描述了由常见的单环氮杂环丁酮前体的非对映异构体6-（1-羟乙基）-2-乙硫基和2-（2-氨基乙硫基）-penem-3-羧酸酯的立体控制合成。铜（I）促进合适的N / C-3 secopenems的环化反应可产生“ isopenems”（7-氧代-2-thia-1-azabicyc10o [3.2.0]-庚-3-烯）作为唯一的双环产品。

  DOI：

  10.1016/s0040-4039(01)81939-0

文献信息

• An efficient nonisocyanate route to polyurethanes via thiol-ene self-addition
  作者：Mariola Calle、Gerard Lligadas、Juan C. Ronda、Marina Galià、Virginia Cádiz

  DOI：10.1002/pola.27347

  日期：2014.11.1

  A novel and efficient strategy for the synthesis of nonisocyanate polyurethanes has been developed via thiol–ene self‐photopolymerization. An aliphatic thiol–ene carbamate monomer (allyl(2‐mercaptoethyl)carbamate, AMC) was synthesized by a one‐step synthesis procedure, from cysteamine and allyl chloroformate. The urethane group was therefore incorporated directly into the monomer precursor, avoiding

  通过硫醇-烯自光聚合，已经开发出一种新颖且有效的合成非异氰酸酯聚氨酯的策略。脂族硫醇烯氨基甲酸酯单体（烯丙基（2-巯基乙基）氨基甲酸酯，AMC）是通过一步合成法由半胱胺和氯甲酸烯丙酯合成的。因此，将氨基甲酸酯基团直接结合到单体前体中，避免了与有毒异氰酸酯有关的问题。使用自由基抑制剂邻苯三酚（1％wt）成功稳定了AMC。另外，使用苯基膦酸作为共添加剂使得其对于较低浓度的邻苯三酚（0.1％wt）稳定。通过在365 nm的紫外线辐射下进行硫醇-烯的光聚合，AMC可直接转变为热塑性聚氨酯（TPU）。T 5％〜325℃）。发现高浓度的邻苯三酚会降低反应速率和光聚合的最终转化率。©2014 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2014，52，3017-3025
• Synthesis of a 4β-carboxyethyl derivative of thienamycin
  作者：Gilles Bouthillier、Harold Mastalerz、Marcel Menard

  DOI：10.1016/s0040-4039(00)76942-5

  日期：1994.7

  A stereoselective synthesis of the 4β-carboxyethyl derivative of thienamycin (1) is described. The stereochemistry of the substituent at C-4 of the carbapenem was obtained by equilibration of the ester group in the 1-azabicyclo[4.2.0]octane intermediates, 8 and 9, with base. This favored the 5α-ester (8) which was then transformed into the imide (14). Regioselective opening of the imide with lithium

  描述了噻吩霉素（1）的4β-羧乙基衍生物的立体选择性合成。碳青霉烯碳原子数为4的取代基的立体化学是通过将1-氮杂双环[4.2.0]辛烷中间体8和9中的酯基与碱平衡而获得的。这有利于5α-酯（8），然后将其转化为酰亚胺（14）。用烯丙氧基锂对酰亚胺进行区域选择性开放，得到氮杂环丁酮（15），将其转化为标题化合物。
• 4-Substituted alkyl carbapenem antibiotics
  申请人：Bristol-Myers Squibb Company

  公开号：EP0433759A1

  公开（公告）日：1991-06-26

  Compounds of the formula wherein R1 is hydrogen, C1-2 alkyl, -CH20H, -CH2NH2, A is an unsubstituted or hydroxy-substituted straight or branched C, -, 10 alkylene group or a straight or branched C1-10 alkylene group having an intervening heteroatom selected from oxygen, sulfur and nitrogen; R2 is hydroxy, halogen, C1-4 alkoxy, nitrile, azido, a quaternary ammonio group, -NRSR6, azetidinyl, or a 5- or 6-membered heterocyclic group selected from heteroaromatic and heteroalicyclic joined through a carbon atom thereof; B is a straight or branched C, -6 alkylene group or a direct bond when R3 is joined to the sulfur atom through a carbon atom thereof; R3 is a residue of an organic group; R4 is hydrogen, a removable carboxy-protecting group or a physiologically hydrolyzable ester group; R5 and R6 each are independently hydrogen, C1-6 alkyl, C1-4 alkoxy, hydroxyethyl, azidoethyl, aminoethyl, and when R5 is hydrogen or C, -a alkyl, R6 is hydroxy, C1-4 alkoxy, amino, C1-4 alkylamino, di(Ci-4.)alkylamino, substituted C1-4 alkyl wherein said alkyl substituent is selected from hydroxy, azido, amino, guanidino, nitrile, carboxy, formimidoyl and phenyl, or an acyl residue of an amino acid or peptide; or R5 and R6, taken together with the nitrogen atom to which they are attached, is an unsubstituted or substituted heterocyclic ring having 1 to 2 ring members and having up to four heteroatoms in each ring independently selected from oxygen, nitrogen and sulfur, wherein said substituent is selected from the group consisting of C1-4 alkyl, C1-4 alkoxy, trifluoromethyl, hydroxy, halogen, amino, nitrile, carboxy, carbamido, carbamoyl, C, -4 alkylamino and amino (C1-4) alkyl; W is a direct bond, oxygen, sulfur or NR'°; Y is oxygen or NR10; Z is hydrogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, -NR7R8, amino(C1-4)alkyl, azido(C1-4)alkyl or hydroxy (C1-4)alkyl; R7 and R8 each are independently hydrogen, C1-4 alkyl or alkanoyl; and R10 is hydrogen, C1-4 alkyl, C1-4 alkylamino or di(C1-4)alkylamino; or a non-toxic pharmaceutically acceptable salt thereof, are novel antimicrobial agents which are useful in the treatment of infectious disease in humans and other animals. Novel intermediates and processes for their preparation are also disclosed.

  式中的化合物 其中 R1 为氢、C1-2 烷基、-CH20H、-CH2NH2、 A 是未取代的或羟基取代的直链或支链 C,-,10-亚烷基，或具有选自氧、硫和氮的杂原子的直链或支链 C1-10 亚烷基； R2 是羟基、卤素、C1-4 烷氧基、腈、叠氮、季铵基、-NRSR6、 氮杂环丁基，或通过一个碳原子连接的 5 或 6 元杂环基团，这些杂环基团选自杂芳族和杂脂环； B 是直链或支链 C, -6 亚烷基，或当 R3 通过其碳原子与硫原子相连时的直接键； R3 是有机基团的残基； R4 是氢、可去除的羧基保护基团或生理上可水解的酯基； R5和R6各自独立地是氢、C1-6烷基、C1-4烷氧基、羟乙基、叠氮乙基、氨基乙基，当R5是氢或C, -a烷基时，R6是羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4.当 R5 为氢或 C-a烷基时，R6 为羟基、C1-4烷氧基、氨基、C1-4烷基氨基、二(Ci-4. )烷基氨基、取代的 C1-4 烷基，其中所述烷基取代基选自羟基、叠氮基、氨基、胍基、腈基、羧基、甲酰亚胺基和苯基，或氨基酸或肽的酰基残基；或 R5 和 R6，连同它们所连接的氮原子，是一个未取代或取代的杂环，具有 1 至 2 个环成员，且每个环中具有最多 4 个独立选自氧、氮和硫的杂原子，其中所述取代基选自由 C1-4 烷基、C1-4 烷氧基、三氟甲基、羟基、卤素、氨基、腈、羧基、氨基甲酰基、氨基甲酰基、C, -4 烷基氨基和氨基（C1-4）烷基组成的组；W 是直接键、氧、硫或 NR'°； Y 是氧或 NR10 Z 是氢、羟基、C1-4 烷基、C1-4 烷氧基、-NR7R8、氨基（C1-4）烷基、叠氮（C1-4）烷基或羟基（C1-4）烷基； R7 和 R8 各自独立地为氢、C1-4 烷基或烷酰基；以及 R10 是氢、C1-4 烷基、C1-4 烷基氨基或二(C1-4)烷基氨基； 或其无毒药学上可接受的盐，是新型抗菌剂，可用于治疗人类和其他动物的传染性疾病。此外，还公开了新型中间体及其制备工艺。
• A New Synthesis of 1β-Alkylcarbapenems Utilizing Eschenmoser Sulfide Contraction of the Novel Thiazinone Intermediates
  作者：Osamu Sakurai、Tsuyoshi Ogiku、Masami Takahashi、Masahito Hayashi、Takeshi Yamanaka、Hiroshi Horikawa、Tameo Iwasaki

  DOI：10.1021/jo960764q

  日期：1996.1.1

  Novel syntheses of the 1,beta-alkylcarbapenems were achieved on the basis of Eschenmoser sulfide contraction via the new bicyclic 1,3-thiazinone intermediates. 1,3-Thiazinones 7, 16, and 25 were effectively prepared from thioesters 5 and 22 using a C4-S bond formation process. The sulfide contraction reactions were performed by treatment of 7, 16, and 25 with base (NaH or KO-t-Bu) in the presence of triphenylphosphine to generate the corresponding carbapenem enolate 12, 17, and 26, which were trapped by (PhO)(2)POCl followed by the reaction with mercaptans to afford carbapenems 10a, 10b, 19, and 28, respectively.
• A new synthetic method of 1β-methylcarbapenems utilizing the eschenmoser sulfide contraction
  作者：Osamu Sakurai、Tsuyoshi Ogiku、Masami Takahashi、Hiroshi Horikawa、Tameo Iwasaki

  DOI：10.1016/s0040-4039(00)76792-x

  日期：1994.4

  1 beta-Methylcarbapenems 7 were synthesized utilizing the Eschenmoser sulfide contraction as a key step in a one-pot procedure from the novel thiazinone intermediate 4 which was easily accessible from the propionic acid derivative 1.