methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate | 71461-39-7

• 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: methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
• 英文别名: methyl 2,2-dimethyl-3-(2,2-dibromo-1-ethenyl)cyclopropanecarboxylate；methyl 2,2-dimethyl-3-(2',2'-dibromovinyl)-cyclopropanecarboxylate；Cyclopropanecarboxylicacid, 3-(2,2-dibromoethenyl)-2,2-dimethyl-, methyl ester, (1R,3R)-rel-；methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 71461-39-7
• 化学式: C₉H₁₂Br₂O₂
• 分子量: 312.001
• InChiKey: YSILGROPIYCDQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸甲酯 在 氢溴酸 、 氢化铝 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以90%的产率得到methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  Transformation of 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylates to the Corresponding 2,2-Dibromoethenyl Analogs by Halogen Exchange Reaction

  摘要：

  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。

  DOI：

  10.1246/bcsj.59.1021

文献信息

• Method for producing cyclopropanecarboxylates
  申请人：——

  公开号：US20020052525A1

  公开（公告）日：2002-05-02

  There is provided a method for producing a cyclopropanecarboxylate of formula (1): 1 which comprises contacting a cyclopropanecarboxylate of formula (2): 2 with a monohydroxy compound of formula (3): R 7 OH  (3) in the presence of a lithium compound of formula (4): R 8 OLi  (4), wherein R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group; R 6 represents an alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; R 7 and R 8 do not simultaneously represent the same and each independently represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

  提供了一种生产公式（1）环丙烷甲酸酯的方法： 1 该方法包括接触 一种公式（2）的环丙烷甲酸酯： 2 与一种公式（3）的单羟基化合物： R 7 OH  (3) 在公式（4）的锂化合物存在下： R 8 OLi  (4)， 其中R 1 ，R 2 ，R 3 ，R 4 和R 5 每个独立代表 一个氢原子，一个卤素原子， 一个取代或不取代的烷基团， 一个取代或不取代的烯丙基团，或 一个取代或不取代的芳基团； R 6 代表一个有1到10个碳原子的烷基团或 一个取代或不取代的苯基团； R 7 和R 8 不同时代表相同的，且每个独立代表 一个取代或不取代的烷基团，或 一个取代或不取代的芳基团。
• Optically active bisoxazoline compounds, process for production of the same and use thereof
  申请人：Itagaki Makoto

  公开号：US20060149077A1

  公开（公告）日：2006-07-06

  Optically active bisoxazoline compounds represented by the general formula (1), a process for producing the compounds, and a process for producing cyclopropanecarboxylic esters by using the same: wherein R 1 and R 2 are the same and each represents C 1-6 alkyl, substituted or unsubstituted aralkyl, or substituted or unsubstituted phenyl or R 1 and R 2 are bonded each other together with the carbon atom of oxazoline ring to which they are bonded to form a ring; R 3 is substituted or unsubstituted naphthyl; R 4 and R 5 are the same and each represent hydrogen or C 1-6 alkyl, or R 4 and R 5 are bonded each other together with the carbon atom to which they are bonded to form a cycloalkyl ring having 3 to 6 carbon atoms; and * represents an asymmetric center.

  光学活性的双噁唑啉化合物由通式（1）表示，制备该化合物的方法以及使用该化合物制备环丙烷羧酸酯的方法： 其中，R1和R2相同，分别表示C1-6烷基，取代或未取代的芳基烷基或取代或未取代的苯基，或者R1和R2相互结合形成环，与它们所连接的噁唑环的碳原子相连；R3是取代或未取代的萘基；R4和R5相同，分别表示氢或C1-6烷基，或者R4和R5相互结合形成有3至6个碳原子的环状烷基环；*表示一个不对称中心。
• Methods for producing cyclopropane carboxylates
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1061065A2

  公开（公告）日：2000-12-20

  There is provided a method for producing a cyclopropanecarboxylate. of formula (3): wherein R1, R2, R3, R4 and R5 each independently represent: a hydrogen atom, halogen atom, an optionally substituted alkyl group and the like; and R7 represents: an optionally substituted alkyl group,and the like, which is characterized by reacting a cyclopropanecarboxylate of the formula (1) wherein R1, R2, R3, R4 and R5 are as defined above, and R6 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group, with a monohydroxy compound of the formula (2):         R7OH     (2) wherein R7 is the same as defined above, in the presence of an alkali metal hydroxide.

  提供了一种生产环丙烷羧酸盐的方法。 其特征在于将式（1）（其中 R1、R2、R3、R4 和 R5 如上定义，R6 代表具有 1 至 10 个碳原子的烷基或任选取代的苯基）的环丙羧酸酯与式 （2）的单羟基化合物反应： R7OH (2) 其中 R7 与上述定义相同，在碱金属氢氧化物存在下。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANE COMPOUND AND ASYMMETRIC COPPER COMPLEX FOR USE IN THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1674445A1

  公开（公告）日：2006-06-28

  A process for producing an optically active cyclopropane compound represented by the formula (4): wherein R3, R4, R5 and R6 are the same or different, and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and so on; and R7 represents a C1-6 alkyl group; and * represents an asymmetric carbon atom, which comprises reacting a prochiral olefin represented by the formula (2): wherein R3, R4, R5, and R6 are as described above, with a diazoacetic acid ester represented by the formula (3):         N2CHCO2R7     (3) wherein R7 is as defined above, in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): wherein R1 represents a hydrogen atom, a C1-6 alkyl group, and so on; R2 represents a C1-6 alkyl group and so on; and n represents an integer of 0 to 3; provided that, two R1s may be bonded each other together with the carbon atom to which they are bonded to form a ring; and * represents an asymmetric carbon atom, and a copper compound, is provided.

  一种生产由式（4）表示的光学活性环丙烷化合物的工艺： 其中 R3、R4、R5 和 R6 相同或不同，代表氢原子、卤素原子、取代或未取代的烷基等；R7 代表 C1-6 烷基；* 代表不对称碳原子、 其中包括使式 (2) 所代表的手性烯烃发生反应： 其中 R3、R4、R5 和 R6 如上所述，与式 (3) 所代表的重氮乙酸酯反应： N2CHCO2R7 (3) 其中 R7 如上定义，在由式（1）代表的光学活性环烷基亚双噁唑啉化合物制备的不对称铜络合物存在下： 其中，R1 代表氢原子、C1-6 烷基等；R2 代表 C1-6 烷基等；n 代表 0 至 3 的整数；条件是两个 R1 可与它们所键合的碳原子一起相互键合以形成环；* 代表不对称碳原子、 以及一种铜化合物。
• Optically active copper catalyst composition
  申请人：Itagaki Makoto

  公开号：US20060211879A1

  公开（公告）日：2006-09-21

  There is provided an optically active copper catalyst composition comprising (a) an optically active salicylideneaminoalcohol represented by the formula (1): wherein R 1 and R 2 are the same or different, and independently represent a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; X 1 and X 2 are the same or different, and independently represent a hydrogen atom, a lower alkoxy group, a nitro group, a lower alkoxycarbonyl group, a cyano group or a halogen atom; and * represents an asymmetric center, provided that both of X 1 and X 2 don't represent hydrogen atoms, (b) a monovalent or divalent copper compound, and (c-1) a lithium compound or (c-2) a compound selected from aluminum compounds having Lewis acidity, titanium compounds having Lewis acidity, boron compounds having Lewis acidity, zirconium compounds having Lewis acidity and hafnium compounds having Lewis acidity; and a process for producing an optically active cyclopropane compound by using the same.

  提供了一种光学活性铜催化剂组合物，该组合物包括 (a) 由式(1)代表的光学活性水杨基氨基醇： 其中 R 1 和 R 2 相同或不同，且各自代表取代或未取代的低级烷基、取代或未取代的芳基或取代或未取代的芳烷基； X 1 和 X 2 相同或不同，且各自代表氢原子、低级烷氧基、硝基、低级烷氧羰基、氰基或卤素原子； * 代表不对称中心，条件是两个 X 1 和 X 2 不代表氢原子、 (b) 一价或二价铜化合物，以及(c-1)锂化合物或(c-2)选自具有路易斯酸性的铝化合物、具有路易斯酸性的钛化合物、具有路易斯酸性的硼化合物、具有路易斯酸性的锆化合物和具有路易斯酸性的铪化合物的化合物；以及使用上述化合物生产光学活性环丙烷化合物的工艺。