2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester | 59898-05-4

• 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: 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester
• 英文别名: ethyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate；2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropanecarboxylic acid ethyl ester；ethyl 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropane-carboxylate；ethyl cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate；ethyl 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropanecarboxylate；ethyl 2-(β,β-dibromovinyl)-3,3-dimethylcyclopropanecarboxylate；Ethyl 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate；ethyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 59898-05-4
• 化学式: C₁₀H₁₄Br₂O₂
• 分子量: 326.028
• InChiKey: VWJAGACCXJKAPO-UHFFFAOYSA-N

物化性质

• 沸点：
  104-105 °C(Press: 0.25 Torr)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester 、 甲基三辛基氯化铵 在 盐酸 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 生成 3-(2,2-二溴乙烯基)-2,2-二甲基-环丙烷-1-羧酸
  参考文献：
  名称：

  Process for the preparation of dihalovinylcyclopropanecarboxylic acids

  摘要：

  本发明涉及一种制备环丙烷羧酸的新工艺，其中环丙烷羧酸的化学式为（I）##STR1## 其中X和Y独立地代表卤素，通过相转移催化剂存在下，在或不在水溶性有机溶剂中，通过相应的具有1到6个碳原子的烷基酯的碱性水解来实现。水解是在2至50重量％的碱性氢氧化物溶液中进行的。如果需要，在适当条件下，可以改变最终产物中原始酯的顺反异构比。化学式（I）的环丙烷羧酸以高纯度获得，并且是杀虫活性拟除虫菊酯的有用中间体。

  公开号：

  US04419524A1
• 作为产物：
  描述：

  ethyl 4,6,6-tribromo-3,3-dimethyl-5-hexenoate 在 sodium 作用下， 以 乙醇 为溶剂， 以83%的产率得到2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-1-carboxylic acid ethylester
  参考文献：
  名称：

  Process for preparing dihalovinylcyclopropanecarboxylates

  摘要：

  描述了二卤乙烯基环丙烷羧酸酯的新合成方法，其中包括强效杀虫剂。该过程始于烯醇与正酯之间的反应，产生γ-不饱和羧酸酯，随后通过催化加入碳四卤化物到双键，并进行脱卤化反应，生成环丙烷衍生物。

  公开号：

  US04214097A1

文献信息

• Process for the preparation of carboxylic acid esters
  申请人：Souda Hiroshi

  公开号：US20050113581A1

  公开（公告）日：2005-05-26

  There is provided a process for preparing a carboxylic acid ester of formula (3): R 2 COOR 1 (3) wherein R 1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, and R 2 is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, an aryl group which may be substituted, a heteroaryl which may be substituted, an aralkyl group which may be substituted, or a heteroarylalkyl group which may be substituted, which process is characterized by the steps of reacting a monohydroxy compound of formula (1): R 1 OH   (1) wherein R 1 is as defined above, with a zirconium compound of formula (6): Zr(OR 8 ) 4 (6) wherein R 8 is an alkyl group or an aryl group which may be substituted and is not the same as R 1 , to prepare a zirconium catalyst, and reacting a carboxylic acid of formula (2): R 2 COOH   (2) wherein R 2 is as defined above, with the monohydroxy compound of formula (1) in the presence of the zirconium catalyst.

  提供了一种制备化学式为(3)的羧酸酯的方法：R2COOR1 (3)，其中R1是可以被取代的烷基、可以被取代的烯基、可以被取代的炔基、可以被取代的芳基或可以被取代的杂芳基烷基，R2是可以被取代的烷基、可以被取代的烯基、可以被取代的炔基、可以被取代的芳基、可以被取代的杂芳基、可以被取代的芳基烷基或可以被取代的杂芳基烷基。该方法的特征在于将化学式为(1)的单羟基化合物：R1OH (1)（其中R1如上定义）与化学式为(6)的锆化合物反应：Zr(OR8)4 (6)（其中R8是可以被取代的烷基或芳基，且不同于R1），制备锆催化剂，然后在锆催化剂存在的情况下，将化学式为(2)的羧酸：R2COOH (2)（其中R2如上定义）与化学式为(1)的单羟基化合物反应。
• Transformation of 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylates to the Corresponding 2,2-Dibromoethenyl Analogs by Halogen Exchange Reaction
  作者：Kiyohide Matsui、Akemi Saito、Kiyosi Kondo

  DOI：10.1246/bcsj.59.1021

  日期：1986.4

  The title transformation is effected with aluminium tribromide or related reagents in over 80% yields without cis-trans isomerization or epimerization. Efficient removal of hydrogen bromide is essential for optimum yields of the desired products. Use of boron tribromide instead of aluminium tribromide results in opening of the cyclopropane ring with no halogen exchange.

  用三溴化铝或相关试剂进行上述转化，收率超过 80%，且无顺反异构或表聚现象。有效去除溴化氢对获得最佳产率的所需产物至关重要。使用三溴化硼而不是三溴化铝可打开环丙烷环，且无卤素交换。
• Preparation of dihalogenovinylcyclopropanecarboxylic acids and esters
  申请人：Bayer Aktiengesellschaft

  公开号：US04217300A1

  公开（公告）日：1980-08-12

  A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine, R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atoms form a cycloaliphatic ring with up to 7 carbon atoms, and R.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl, which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)-propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl, with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH. The end products are insecticidally active and can also be used as intermediates for producing other insecticides.

  一种制备二卤代乙烯环丙烷羧酸或其酯的方法，其化学式为##STR1##其中Hal分别为氟、氯或溴，R.sup.1和R.sup.2分别为氢或C.sub.1-4-烷基，或者R.sup.1和R.sup.2与相邻的碳原子形成含有最多7个碳原子的环脂环，R.sup.3为氢、C.sub.1-4-烷基或可选择地取代的芳基甲基或杂原芳基甲基，包括将化学式为##STR2##的3-氯-2-(2',2'-二卤代乙烯)-丙烷羧酸酯与碱反应。丙烷羧酸酯是新的，可以通过将化学式为##STR3##的3-(2',2'-二卤代乙烯)-γ-丁内酯与氯化剂反应，然后与化学式为R.sup.4--OH的醇反应来原位形成。最终产物具有杀虫活性，也可用作生产其他杀虫剂的中间体。
• Process for converting 2,2-dichlorovinylcyclopropanes to dibromovinyl
  申请人：FMC Corporation

  公开号：US04188492A1

  公开（公告）日：1980-02-12

  Treatment of 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acids and esters with aluminum bromide, the reaction product of aluminum and a bromoalkane, or HBr and the product of the reaction of HBr with aluminum or an aluminum salt produces the 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropane analogs.

  将3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸和酯与溴代烷、铝和溴代烷的反应产物或HBr以及铝或铝盐的反应产物一起处理，可以得到3-(2,2-二溴乙烯基)-2,2-二甲基环丙烷类似物。
• Chiral copper complex and production processes thereof and using the same
  申请人：Kamitamari Masashi

  公开号：US20050090684A1

  公开（公告）日：2005-04-28

  There is disclosed an optically active salicylideneaminoalcohol compound of formula (1): wherein R 1 represents an alkyl group or the like, R 2 represents an aryl group and the like, and when X 1 represents a nitro, X 2 is a hydrogen atom, when X 1 represents a chlorine atom, X 2 is a chlorine atom, and when X 1 is a hydrogen atom, X 2 is a fluorine atom; and the carbon atom denoted by “*” is an asymmetric carbon atom having either an S or R configuration, and a chiral copper complex produced from the optically active salicylidenaminoalcohol compound and a copper compound.

  公开了一种光学活性的萨利基利丙氨醇化合物，其化学式为(1)：其中，R1代表烷基或类似物，R2代表芳基或类似物，当X1代表硝基时，X2是氢原子，当X1代表氯原子时，X2是氯原子，当X1是氢原子时，X2是氟原子；而由光学活性萨利基利丙氨醇化合物和铜化合物制备的手性铜络合物中，用“*”表示的碳原子是具有S或R构型的不对称碳原子。