methyl trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylate

• 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 trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylate
• 英文别名: Methyl 3-(hydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylate
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: DFJHWVYCBLACJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 碳酸氢钠 、 sodium thiosulfate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.5h， 以93.7%的产率得到methyl (+/-)-cis,trans-3-formyl-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  EP2053037

  摘要：

  公开号：
• 作为产物：
  描述：

  甲醇 、 (+)-ethyl cis-3,3-dimethyl-2-(acetoxymethyl)cyclopropanecarboxylate 、 (+)-ethyl cis-3,3-dimethyl-2-(acetoxymethyl)cyclopropanecarboxylate 、 sodium methylate 在 盐酸 、 水 作用下， 以 甲苯 为溶剂， 65.0~110.0 ℃ 、101.0 kPa 条件下， 反应 3.0h， 以97.8%的产率得到methyl trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylate
  参考文献：
  名称：

  EP2053037

  摘要：

  公开号：

文献信息

• Oxabicyclo 3.1.0 hexanes useful in the production of cyclopropanecarboxylate insecticides and intermediate compounds
  申请人：FMC Corporation

  公开号：EP0003666A1

  公开（公告）日：1979-08-22

  The invention provides compounds of the formulae: in which R is hydrogen or CX3. each X, which is the same as or different from the other, is a chlorine or bromine atom, R' is lower alkyl or lower alkoxy, R2 is hydrogen, lower alkoxycarbonyl or lower alkanoyl, and R3 is hydrogen or lower alkoxycarbonyl. The compounds of Formula III are made by intramolecular carbenoid cyclization of compounds of Formula II; the compounds of Formula II are made from compounds of Formula I, e.g. by treatment with azide followed by a base; the compounds of Formula I are prepared by reacting an alcohol of formula: with a hydrazone. Those compounds of Formula I in which R is CX3 can be converted to a compound of the formula: in which the carboxy and dihalovinyl groups are cis with respect to each other, which are insecticidal, by treatment with certain metals in selected solvents.

  本发明提供了以下式子的化合物： 其中R为氢或CX3.与之相同或不同的各X为氯原子或溴原子，R'为低级烷基或低级烷氧基，R2为氢、低级烷氧羰基或低级烷酰基，R3为氢或低级烷氧羰基。 式 III 的化合物是通过式 II 的化合物的分子内类碳环化反应制得的；式 II 的化合物是由式 I 的化合物制得的，例如先用叠氮化物处理，再用碱处理；式 I 的化合物是通过式......的醇与腙反应制备的： 与腙反应制得。 其中 R 为 CX3 的式 I 化合物可转化为式： 其中羧基和二卤乙烯基互为顺式基团的化合物，可通过在选定溶剂中使用某些金属进行处理而获得杀虫效果。
• PROCESS FOR PRODUCTION OF 2-(HYDROXYMETHYL)CYCLO- PROPANECARBOXYLIC ACIDS
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1538141A1

  公开（公告）日：2005-06-08

  There is provided a production method of a compound of formula (2): wherein R1, R2 and R3 are as defined below,    which comprises reacting    a 2-(hydroxymethyl)cyclopropanecarboxylic compound of formula (1): wherein and R1 represent a hydrogen, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group,    R2 and R3 are the same or different and represent a hydrogen atom or a methyl group, and    R4 represents C1-2 alkyl group substituted with at lest one group selected from the group consisting of a substituted aryl group and an unsubstituted aryl group,    with a hydrogen-donor in the presence of a catalyst selected from the group consisting of ruthenium catalyst, cobalt catalyst, rhodium catalyst, nickel catalyst, palladium catalyst and a platinum catalyst.

  提供了一种式(2)化合物的生产方法： 其中 R1、R2 和 R3 定义如下、 其中包括以下反应 式 (1) 的 2-(羟甲基)环丙烷羧酸化合物： 其中 R1 代表氢、直链、支链或环状烷基、取代或未取代的芳基、 R2 和 R3 相同或不同，代表氢原子或甲基，以及 R4 代表被至少一个选自取代芳基和未取代芳基的基团取代的 C1-2 烷基、 在选自钌催化剂、钴催化剂、铑催化剂、镍催化剂、钯催化剂和铂催化剂组成的催化剂存在下，与氢-载体反应。
• PROCESS FOR PRODUCTION OF TRANS-2,2-DIMETHYL- 3-FORMYLCYCLOPROPANE CARBOXYLIC ACID ESTER
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2053037A1

  公开（公告）日：2009-04-29

  A process for production of a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester comprising: (A) a step of obtaining a mixture containing a trans-2,2-dimethyl-3-(hydroxymethyl)cyclopropanecarboxylic acid ester, (B) a step of conducting an oxidation treatment of the mixture obtained in the step (A) to obtain a mixture containing a crude trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester, (C) a step of contacting the mixture obtained in the step (B) with an aqueous alkali metal hydrogen sulfite solution to obtain an alkali metal salt of a trans-2,2-dimethyl-3-[(hydroxy)(sulfo)methyl]cyclopropanecarboxylic acid ester, and (D) a step of contacting the alkali metal salt obtained in the above-mentioned step (C) with a base or the like to obtain a trans-2,2-dimethyl-3-formylcyclopropanecarboxylic acid ester.

  一种反式-2,2-二甲基-3-甲酰基环丙烷羧酸酯的生产工艺，包括 (A) 第一步：获得含有反式-2,2-二甲基-3-(羟甲基)环丙烷羧酸酯的混合物、 (B) 对步骤(A)中获得的混合物进行氧化处理，以获得含有粗反式-2,2-二甲基-3-甲酰基环丙烷羧酸酯的混合物、 (C) 将步骤(B)中得到的混合物与碱金属亚硫酸氢盐水溶液接触，得到反式-2,2-二甲基-3-[(羟基)(磺基)甲基]环丙烷羧酸酯的碱金属盐，和 (D) 将上述步骤（C）中得到的碱金属盐与碱或类似物质接触，得到反式-2,2-二甲基-3-甲酰基环丙烷羧酸酯。
• Process for production of formylcyclopropanecarboxylic ester
  申请人：Minamida Ryo

  公开号：US20050240050A1

  公开（公告）日：2005-10-27

  There is provided a production method of formylcyclopropanecarboxylate compound of formula (2): wherein R 1 and R 2 are as defined below, which comprises reacting a cyclopropanecarboxylate compound of formula (1): wherein and R 1 represent a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, R 2 represents a hydrogen atom or a methyl group, with at least one oxidizer selected from the group consisting of hypohalite, N-halosuccinimide, a trichloroisocyanuric acid, and iodine, in the presence of a nitroxy radical compound.

  提供了一种式(2)的甲酰基环丙烷羧酸化合物的生产方法： 其中 R 1 和 R 2 定义如下、 其中包括 式 (1) 的环丙烷羧酸化合物： 其中和 R 1 代表直链、支链或环状烷基、取代或未取代的芳基或取代或未取代的芳烷基、 R 2 代表氢原子或甲基，在硝基化合物的存在下，与至少一种选自次卤酸、N-卤代丁二酰亚胺、三氯异氰尿酸和碘组成的组的氧化剂反应。
• Process for production of 2-(hydroxymethyl)cyclo-propanecarboxylic acids
  申请人：Minamida Ryo

  公开号：US20050288526A1

  公开（公告）日：2005-12-29

  There is provided a production method of a compound of formula (2): wherein R 1 , R 2 and R 3 are as defined below, which comprises reacting a 2-(hydroxymethyl)cyclopropanecarboxylic compound of formula (1): wherein and R 1 represent a hydrogen, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, R 2 and R 3 are the same or different and represent a hydrogen atom or a methyl group, and R 4 represents C1-2 alkyl group substituted with at lest one group selected from the group consisting of a substituted aryl group and an unsubstituted aryl group, with a hydrogen-donor in the presence of a catalyst selected from the group consisting of ruthenium catalyst, cobalt catalyst, rhodium catalyst, nickel catalyst, palladium catalyst and a platinum catalyst.

  提供了一种式(2)化合物的生产方法： 其中 R 1 , R 2 和 R 3 的定义如下、 其中包括 式（1）的 2-（羟甲基）环丙烷羧酸化合物： 其中和 R 1 代表氢、直链、支链或环状烷基、取代或未取代的芳基、 R 2 和 R 3 相同或不同，代表氢原子或甲基，以及 R 4 代表在选自钌催化剂、钴催化剂、铑催化剂、镍催化剂、钯催化剂和铂催化剂的催化剂存在下，被至少一个选自取代芳基和未取代芳基的基团取代的 C1-2 烷基。