trans 2,2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid | 25312-79-2

• 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: trans 2,2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid
• 英文别名: (+/-)-cis,trans-3-formyl-2,2-dimethylcyclopropanecarboxylic acid；trans 3-formyl-2,2-dimethyl-cyclopropanecarboxylic acid；2,2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid；2,2-dimethyl-3-formyl-cyclopropane-carboxylic acid；3-formyl-2,2-dimethylcyclopropane carboxylic acid；3-formyl-2,2-dimethyl-cyclopropanecarboxylic acid；3-Formyl-2,2-dimethylcyclopropane-1-carboxylic acid
• CAS: 25312-79-2
• 化学式: C₇H₁₀O₃
• mdl: MFCD19228206
• 分子量: 142.155
• InChiKey: PTQGFDXPHNRDCV-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  249.8±33.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans 2,2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid 在 4-二甲氨基吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 β-丙氨酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 21.0h， 生成 α-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(3,4-dichloro-2,5-dioxo-3-cyclopenten-1-ylidenemethyl)-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Pyrethroids Having Halogen, Keto, or Nitro Group-Containing Substituents

  摘要：

  Thirteen pyrethroid esters, most of which contain strong electron-withdrawing groups (e.g., halomethylketo and nitro groups) in the side chain of the cyclopropane acid moiety, have been synthesized. The synthesis involved the reaction of various active methylene compounds with 3-formyl-2,2-dimethylcyclopropanecarboxylic esters of known pyrethroid alcohols. Rather than the usually employed Wittig reaction for these syntheses, the novel pyrethroid acid moieties were prepared by amino acid-catalyzed Knoevenagel condensations under mild conditions. Preliminary toxicity studies of the pyrethroid esters, against several insect and one mite species, were conducted. Two of these compounds had good repellent activity against the twospotted spider mite (Tetranychus urticae) at 100 ppm, and six of them had medium insecticidal activity against either black bean aphid (Aphis fabae) or western potato leafhopper (Empoasca abrupta) at 10 ppm.

  DOI：

  10.1021/jf00056a060
• 作为产物：
  描述：

  3-(Dimethoxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid 生成 trans 2,2-dimethyl-3-formyl-cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  MARTEL, J.;TESSIER, J.;DEMOUTE, J. -P.

  摘要：

  DOI：

文献信息

• Process for Producing 3-(2-Cyano-1-propenyl)-2,2- Dimethylcyclopropanecarboxylic Acid or Salt Thereof
  申请人：Uekawa Toru

  公开号：US20120016150A1

  公开（公告）日：2012-01-19

  A process for producing comprising reacting a 3-formyl-2,2-dimethylcyclopropanecarboxylate and propionitrile in the presence of a base to obtain 3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid or its salt.

  生产过程包括在碱的存在下，通过将3-甲酰基-2,2-二甲基环丙基羧酸酯和丙腈反应，得到3-(2-氰丙烯基)-2,2-二甲基环丙基羧酸或其盐。
• Novel esters of 2-methyl-3-allyl-4-substituted-cyclopent-2-ene-1-yl
  申请人：Roussel Uclaf

  公开号：US04356187A1

  公开（公告）日：1982-10-26

  Novel esters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN, R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, halogen, alkenyl of 2 to 3 carbon atoms and alkyl of 1 to 3 carbon atoms, Y' is selected from the group consisting of ##STR2## R.sub.4 ' and R.sub.5 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, fluorine, bromine, chlorine and R.sub.4 ' and R.sub.5 ' together with the carbon atom to which they are attached form an optionally unsaturated hydrocarbon ring or heterocycle of 3 to 7 chain members and a heterocycle of the formula X is selected from the group consisting of sulfur and oxygen or R.sub.4 ' is cyano and R.sub.5 ' is phenyl or R.sub.4 ' is hydrogen and R.sub.5 ' is selected from the group consisting of cyano, ##STR3## AlK is alkyl of 1 to 4 carbon atoms, the double bond in the 1- position of the vinyl side chain of formula (A) having (E) or (Z) configuration, R.sub.6 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and alkoxycarbonyl of 2 to 5 carbon atoms, the substituents on the cyclopropane ring of formula (A) and (C) have the cis or trans, racemic or optically active configuration, Z.sub.1 is alkyl of 1 to 4 carbon atoms, Z.sub.2, Z.sub.3 and Z.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms and halogen and the asymetric carbon of formula (D) may be (S) or (R) configuration or a racemic mixture thereof and the carbon atom in the 1- position of the alcohol moiety may have (R), (S) or racemic configuration having insecticidal properties and their preparations.

  公式为##STR1##的新酯类化合物，其中R.sub.1和R.sub.2分别选自羰酰基和R.sub.1'和R.sub.2'，R.sub.1'和R.sub.2'分别选自氢、卤素、1至6个碳原子的烷基、6至10个碳原子的芳基、7至13个碳原子的芳基烷基、2至5个碳原子的烷氧羰基和--CN的群，R.sub.3和R.sub.3'分别选自氢、卤素、2至3个碳原子的烯基和1至3个碳原子的烷基，Y'选自##STR2##的群，R.sub.4'和R.sub.5'分别选自氢、1至4个碳原子的烷基、氟、溴、氯和R.sub.4'和R.sub.5'与其连接的碳原子一起形成3至7个链成员的可选不饱和碳氢环或杂环，以及公式X的杂环选自硫和氧或R.sub.4'为氰基且R.sub.5'为苯基或R.sub.4'为氢且R.sub.5'选自氰基、##STR3##，AlK为1至4个碳原子的烷基，公式(A)的乙烯侧链的1-位置的双键具有(E)或(Z)构型，R.sub.6选自氢、1至4个碳原子的烷基和2至5个碳原子的烷氧羰基，公式(A)和(C)的环丙烷环上的取代基具有顺式或反式、消旋或光学活性构型，Z.sub.1为1至4个碳原子的烷基，Z.sub.2、Z.sub.3和Z.sub.4分别选自氢、1至4个碳原子的烷基、1至4个碳原子的烷氧基、1至4个碳原子的烷硫基和卤素，公式(D)的不对称碳原子可能为(S)或(R)构型或其消旋混合物，醇基的1-位置的碳原子可能具有(R)、(S)或消旋构型，具有杀虫性能的化合物及其制备方法。
• Preparation of substituted alpha-halogeno-propionic acids and their
  申请人：Bayer Aktiengesellschaft

  公开号：US04440947A1

  公开（公告）日：1984-04-03

  Substituted .alpha.-halogenopropionic acids and their derivatives of the general formula ##STR1## wherein R.sup.1 to R.sup.3, Y and X have the meanings given in the description, are prepared by a process which is characterized in that substituted vinylidene chlorides of the general formula ##STR2## are reacted with chlorine or bromine chloride in the presence of compounds of the formula R.sup.5 --SO.sub.3 R.sup.6 (III) wherein R.sup.5 and R.sup.6 have the meaning given in the description, and the products obtained are treated, if appropriate, with water or alcohol. Certain of the substituted .alpha.-halogeno-propionic acids and the substituted vinylidene chloride of the formula ##STR3## are new. The end products are useful as herbicides and intermediates for insecticides.

  通用公式##STR1##中的取代.alpha.-卤代丙酸及其衍生物，其中R.sup.1至R.sup.3，Y和X的含义如描述中所示，通过以下过程制备，该过程的特征在于，在化合物R.sup.5-SO.sub.3R.sup.6（III）的存在下，取代乙烯基氯化物的一般公式##STR2##与氯或溴氯在存在下反应，其中R.sup.5和R.sup.6的含义如描述中所示，并且如有必要，所得产品经水或醇处理。某些取代.alpha.-卤代丙酸和一般公式##STR3##的取代乙烯基氯化物是新的。最终产品可用作除草剂和杀虫剂的中间体。
• Insecticidal esters
  申请人：Roussel Uclaf

  公开号：US04489093A1

  公开（公告）日：1984-12-18

  Novel esters in all possible isomeric forms of the formula ##STR1## wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkyl-alkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, ##STR2## aryl optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, ##STR3## R' is alkyl of 1 to 8 carbon atoms, R" and R"' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.sub.3 are individually alkyl of 1 to 18 carbon atoms (b) aryl of 6 to 14 carbon atoms optionally substituted with at least one substituent selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --OCF.sub.3, --CF.sub.3 and --SCF.sub.3 and (c) heterocycle optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF.sub.3, --OCF.sub.3 and --SCF.sub.3, B is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms, optionally unsaturated cycloalkyl of 3 to 18 carbon atoms and the remainder of an alcohol used in synthesis of pyrethrinoid esters, X is halogen and the ethylenic double bond may have Z or E geometry having parasitic activity, especially insecticidal acaricidal and nematocidal activity.

  该公式的所有可能异构形式中的新酯物，其中R从以下组中选择：(a) 可选择不饱和的1到8个碳原子的烷基或可选择不饱和的3到8个碳原子的环烷基或环烷基烷基，可选地用卤素、苯基或可选择地用至少一种成员取代的羟基、1到8个碳原子的烷氧基、1到8个碳原子的烷基、卤素、R'为1到8个碳原子的烷基，R"和R"'分别从氢和1到8个碳原子的烷基组成的组中选择，AlK.sub.1、AlK.sub.2和AlK.sub.3分别为1到18个碳原子的烷基；(b) 6到14个碳原子的苯基，可选择地用至少一种取代基取自羟基、1到8个碳原子的烷氧基、1到8个碳原子的烷基、卤素、--OCF.sub.3、--CF.sub.3和--SCF.sub.3；(c) 可选择地用至少一种成员取代的杂环烃，取自--OH、1到8个碳原子的烷氧基、1到8个碳原子的烷基、卤素、--CF.sub.3、--OCF.sub.3和--SCF.sub.3，B从以下组中选择：可选择不饱和的1到18个碳原子的烷基、可选择不饱和的3到18个碳原子的环烷基和合成拟除虫酯的醇的剩余部分，X为卤素，乙烯双键可能具有寄生活性，特别是具有杀虫、杀螨和杀线虫活性的Z或E几何结构。
• Cyclopropane carboxylic acid derivatives
  申请人：Roussel Uclaf

  公开号：US04556666A1

  公开（公告）日：1985-12-03

  All stereoisomeric forms and mixtures of stereoisomers of compounds of the formula ##STR1## wherein X is selected from the group consisting of oxygen, sulfur, sulfoxide and sulfone, R.sub.1 and R.sub.3 are individually selected from the group consisting of optionally unsaturated alkyl of 1 to 7 carbon atoms and optionally unsaturated cycloalkyl of 3 to 7 carbon atoms optionally substituted with at least one halogen and optionally interrupted with at least one heteroatom and aryl and aralkyl of 6 to 18 carbon atoms and R.sub.2 is the residue of a R.sub.2 OH alcohol used in pyrethrinoids synthesis having pesticidal activity and their preparation and novel intermediates.

  化合物的所有立体异构形式和立体异构体混合物的化学式为##STR1##其中X选自氧、硫、亚砜和砜的组成群，R.sub.1和R.sub.3分别选自1至7个碳原子的可选不饱和烷基和3至7个碳原子的可选不饱和环烷基，可选地取代至少一种卤素和可选地中断至少一种杂原子以及6至18个碳原子的芳基和芳基烷基，R.sub.2是在拟除虫剂活性的拟拟拟拟合成中使用的R.sub.2 OH醇的残基及其制备方法和新颖中间体。