1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene | 113274-29-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 炔丙基型1，3-偶极有机化合物
• 英文名称: 1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene
• 英文别名: 3-carbethoxy-1-(2-chloroethyl)-3-methyltriazene；1-(2-Chloroethyl)-3-methyl-3-carbethoxytriazene；ethyl N-(2-chloroethyldiazenyl)-N-methylcarbamate
• CAS: 113274-29-6
• 化学式: C₆H₁₂ClN₃O₂
• 分子量: 193.633
• InChiKey: USWACFKAYKLOCN-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 0.003 Torr)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene 在 水 作用下， 以 乙腈 为溶剂， 生成 氨基甲酸乙酯 、 乙二醇 、 乙醛 、 2-氯乙醇
  参考文献：
  名称：

  1,3-Dialkyl-3-acyltriazenes: products and rates of decomposition in acidic and neutral aqueous solutions

  摘要：

  The products and mechanism of hydrolytic decomposition of a series of 1,3-dialkyl-3-acyltriazenes were studied in both acidic and neutral buffers. In the acidic region, the products are alkyl alcohols derived from the N(1) alkyl group and amides derived from the intact N(3) portion of the molecule. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is less than 1.0. The mechanism is specific acid catalyzed, involving rapid reversible protonation of the 3-acyl group followed by scission of the N(2)-N(3) bond to generate an amide and an alkyl diazonium ion. The (2-hydroxyethyl)diazonium ion gives ethylene glycol and acetaldehyde, while the (2-chloroethyl)diazonium ion yields 2-chloroethanol. In the neutral region, the products are similar to those found in acidic buffers, alkyl alcohols, and amides. At this pH the (2-chloroethyl)diazonium ion produces ethylene glycol and acetaldehyde in addition to 2-chloroethanol. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is greater than 1.0. The mechanism involves unimolecular heterolysis of the N(2)-N(3) bond to form an amide anion and an alkyldiazonium ion. The methyldiazonium ion leads to incorporation of deuterium in the methyl group of the products, indicating the existence of an equilibrium between the metastable methyldiazonium ion and diazomethane.

  DOI：

  10.1021/jo00028a047
• 作为产物：
  描述：

  1-<2-(tert-butyldimethylsiloxy)-ethyl>-3-carbethoxy-3-methyltriazene 在 四氯化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene
  参考文献：
  名称：

  Novel cross-linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes

  摘要：

  DOI：

  10.1021/jo00242a022
• 作为试剂：
  描述：

  三苯基膦 、 乙基(2Z)-3-(2-羟基乙基)-1-甲基-2-三氮烯-1-羧酸酯 、 、 四氯化碳 在 氮气 、 三苯基氧化膦 、 乙醚 、 Silica Gel 、 正戊烷 、 1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene 作用下， 以 正戊烷 为溶剂， 反应 20.0h， 以produced 1.22 g (6:30×10-3 mol, 58.3%) of the desired compound, 3-carboethoxy-(2-chloroethyl)-3-methyltriazene, 6a的产率得到1-(2-chloroethyl)-3-ethoxycarbonyl-3-methyltriazene
  参考文献：
  名称：

  Substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazenes

  摘要：

  一种代替的1-(2-氯乙基)-3-酰基-3-烷基-1,2,3-三氮唑，其化学式为：##STR1## 其中R.sub.1为1-氧代烷基，含有2至8个碳原子，含有最多三个氟原子的氟代1-氧代烷基，苯甲酰基，苯乙酰基，含有2至8个碳原子的羧烷氧基，含有2至8个碳原子和最多三个氟原子的氟代羧烷基，羧苯氧基，N-苯基氨基甲酰基，含有2至8个碳原子的N-烷基氨基甲酰基，硫代氨基甲酰基，含有2至8个碳原子的N-烷基硫代氨基甲酰基，N-苯基硫代氨基甲酰基，其中烷基基团可以相同或不同，每个含有1至7个碳原子的二烷基膦酸酯，苯基磺酰基，以及在其中meta或para位取代基为甲基，乙基，甲氧基，乙氧基，氟和氯的meta或para-取代苯基磺酰基； R.sub.2独立地为含有1至7个碳原子的烷基，含有2至7个碳原子和1至3个氟原子的氟代烷基，其中氟代烷基的α-碳未被氟原子取代，苄基，meta或para-取代苄基，其中meta或para取代基为氯，氟和含有1至3个碳原子的烷氧基，含有2至7个碳原子的烯基和含有2至7个碳原子的炔基，可用作抗肿瘤剂。

  公开号：

  US04923970A1

文献信息

• Novel cross-linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes
  作者：Richard H. Smith、Andrew F. Mehl、Donald L. Shantz、Gwendolyn N. Chmurny、Christopher J. Michejda

  DOI：10.1021/jo00242a022

  日期：1988.4
• 1,3-Dialkyl-3-acyltriazenes: products and rates of decomposition in acidic and neutral aqueous solutions
  作者：Richard H. Smith、Brian D. Wladkowski、Julie A. Herling、Timothy D. Pfaltzgraff、Brunon Pruski、John Klose、Christopher J. Michejda

  DOI：10.1021/jo00028a047

  日期：1992.1

  The products and mechanism of hydrolytic decomposition of a series of 1,3-dialkyl-3-acyltriazenes were studied in both acidic and neutral buffers. In the acidic region, the products are alkyl alcohols derived from the N(1) alkyl group and amides derived from the intact N(3) portion of the molecule. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is less than 1.0. The mechanism is specific acid catalyzed, involving rapid reversible protonation of the 3-acyl group followed by scission of the N(2)-N(3) bond to generate an amide and an alkyl diazonium ion. The (2-hydroxyethyl)diazonium ion gives ethylene glycol and acetaldehyde, while the (2-chloroethyl)diazonium ion yields 2-chloroethanol. In the neutral region, the products are similar to those found in acidic buffers, alkyl alcohols, and amides. At this pH the (2-chloroethyl)diazonium ion produces ethylene glycol and acetaldehyde in addition to 2-chloroethanol. The solvent deuterium isotope effect (k(H2O)/k(D2O)) is greater than 1.0. The mechanism involves unimolecular heterolysis of the N(2)-N(3) bond to form an amide anion and an alkyldiazonium ion. The methyldiazonium ion leads to incorporation of deuterium in the methyl group of the products, indicating the existence of an equilibrium between the metastable methyldiazonium ion and diazomethane.
• Substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazenes
  申请人：Bionetics Research, Inc.

  公开号：US04923970A1

  公开（公告）日：1990-05-08

  A substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazene of the formula: ##STR1## in which R.sub.1 is 1-oxoalkyl containing from two to eight carbon atoms, fluorinated 1-oxoalkyls containing from two to eight carbon atoms and substituted with up to three fluorine atoms, benzoyl, phenylacetyl, carboalkoxy containing from two to eight carbon atoms, fluorinated carboalkyl containing from two to eight carbon atoms and up to three fluorine atoms, carbophenoxy, N-phenyl aminocarbonyl, N-alkyl aminocarbonyl containing from two to eight carbon atoms, thiocarbamoyl, N-alkylthiocarbamoyls with from two to eight carbon atoms, N-phenylthiocarbamoyl, dialkylphosphonates in which the alkyl groups can be the same or different and each contains from one to seven carbon atoms, phenylsulfonyl, and meta or para-substituted phenylsulfonyl in which the meta or para substituent is methyl, ethyl, methoxy, ethoxy, fluoro and chloro; and R.sub.2 is indepedently alkyl containing from one to seven carbon atoms, fluoroalkyl containing from two to seven carbon atoms and from one to three fluorine atoms in which the .alpha. carbon of the fluoroalkyl group is not substituted with fluorine, benzyl, meta or para-substituted benzyl in which the meta or para substituent is chloro, fluoro, and alkoxy with from one to three carbon atoms, alkenyl containing from two to seven carbon atoms, and alkynyl containing from two to seven carbon atoms, useful as antitumor agents.

  一种代替的1-(2-氯乙基)-3-酰基-3-烷基-1,2,3-三氮唑，其化学式为：##STR1## 其中R.sub.1为1-氧代烷基，含有2至8个碳原子，含有最多三个氟原子的氟代1-氧代烷基，苯甲酰基，苯乙酰基，含有2至8个碳原子的羧烷氧基，含有2至8个碳原子和最多三个氟原子的氟代羧烷基，羧苯氧基，N-苯基氨基甲酰基，含有2至8个碳原子的N-烷基氨基甲酰基，硫代氨基甲酰基，含有2至8个碳原子的N-烷基硫代氨基甲酰基，N-苯基硫代氨基甲酰基，其中烷基基团可以相同或不同，每个含有1至7个碳原子的二烷基膦酸酯，苯基磺酰基，以及在其中meta或para位取代基为甲基，乙基，甲氧基，乙氧基，氟和氯的meta或para-取代苯基磺酰基； R.sub.2独立地为含有1至7个碳原子的烷基，含有2至7个碳原子和1至3个氟原子的氟代烷基，其中氟代烷基的α-碳未被氟原子取代，苄基，meta或para-取代苄基，其中meta或para取代基为氯，氟和含有1至3个碳原子的烷氧基，含有2至7个碳原子的烯基和含有2至7个碳原子的炔基，可用作抗肿瘤剂。