(1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid methyl ester | 41301-44-4

• 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: (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid methyl ester
• 英文别名: methyl (1S,3S)-3-formyl-2,2-dimethylcyclopropane-1-carboxylate；methyl 1S,3S (trans) hemicaronic aldehyde；methyl trans 1S,3S hemicaronic aldehyde；(1S,3S)-hemicaronaldehyde；Methyl (1S,3S) 2,2-dimethyl-3-formyl-cyclopropane-carboxylate；trans-3,3-Dimethyl-2-formyl-cyclopropan-1-carbonsaeure-methylester；Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate
• CAS: 41301-44-4
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: KVSRWNPBUMDYOQ-NTSWFWBYSA-N

物化性质

• 沸点：
  186.8±33.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid methyl ester 、 亚乙基(三苯基)-lambda~5~-磷烷 以 四氢呋喃 为溶剂， 生成 (1S)-trans-norchrysanthemic acid methyl ester
  参考文献：
  名称：

  Synthesis of All Stereoisomers of the Norchrysanthemic Acid Methyl Ester

  摘要：

  Syntheses of eight stereoisomers of methyl norchrysanthemate, (1R)-trans-(Z)-isomer and (1R)-trans-(E)-isomer from (IR)-trans-chrysanthemic acid, and other six isomers from (+)-3-carene, are described.

  DOI：

  10.1081/scc-120028630
• 作为产物：
  描述：

  cis-caronaldehyde 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 生成 (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of All Stereoisomers of the Norchrysanthemic Acid Methyl Ester

  摘要：

  Syntheses of eight stereoisomers of methyl norchrysanthemate, (1R)-trans-(Z)-isomer and (1R)-trans-(E)-isomer from (IR)-trans-chrysanthemic acid, and other six isomers from (+)-3-carene, are described.

  DOI：

  10.1081/scc-120028630

文献信息

• Stereoselective synthesis of methyl (1R) - and (1R) -hemicaronaldehydes from natural tartaric acid: Application to the synthesis of s-bioallethrin and deltamethrin insecticides§
  作者：A. Krief、W. Dumont、P. Pasau、Ph. Lecomte

  DOI：10.1016/s0040-4020(01)80130-7

  日期：1989.1

  Very efficient enantioselective syntheses of (1R)--and -hemicaronaldehydes precursors of (1R)-trans chrysanthemic acid and its (1R)-cis dibromovinyl analogue starting from natural tartaric acid or D-mannitol are described. They are based on the reaction between isopropylidenetriphenylphosphorane or isopropylidenediphenylsulfurane and chiral γ-alkoxy-α,β-unsaturated esters. The general problem of the

  描述了从天然酒石酸或D-甘露糖醇开始的（1R）-反式菊酸的（1R）-和-半甲基乙醛前体及其（1R）-顺式二溴乙烯基类似物的非常有效的对映选择性合成。它们基于异丙基亚丙基三苯基膦或异丙基二烯基二苯基硫磺与手性γ-烷氧基-α，β-不饱和酯之间的反应。讨论了将非对映选择性加成到这些酯中的一般问题。
• From tartaric acid to the most biologically active insecticides
  作者：A. Krief、W. Dumont、P. Pasau

  DOI：10.1016/0040-4039(88)85340-1

  日期：1988.1

  the ester has a great influence on the stereo-chemistry of the resulting cyclopropane derivative. This reaction has been successfully used for the synthesis of chrysanthemic acid from diester derived from natural tartaric acid.

  异亚丙基三苯苯基膦烷与γ-烷氧基α，β-不饱和酯反应，生成γ-烷氧基环丙烷羧酸酯。酯中碳-碳双键的立体化学对所得环丙烷衍生物的立体化学有很大影响。该反应已成功用于从天然酒石酸衍生的二酯合成菊酸。
• Synthesis and Insecticidal Activity of an Oxabicyclolactone and Novel Pyrethroids
  作者：Elson Alvarenga、Vânia Carneiro、Gabriela Resende、Marcelo Picanço、Elizeu Farias、Mayara Lopes

  DOI：10.3390/molecules171213989

  日期：——

  from furfural is described. Photochemical addition of isopropyl alcohol to furan-2(5H)-one afforded 4-(1'-hydroxy-1'-methylethyl)tetrahydro-furan-2-one (3). The alcohol 3 was directly converted into 4-(1'-bromo-1'-methylethyl)-tetrahydrofuran-2-one (5) in 50% yield by reaction with PBr3 and SiO2. The final step was performed by cyclization of 5 with potassium tert-butoxide in 40% yield. The novel pyrethroids

  溴氰菊酯是拟除虫菊酯的一种，是最安全的杀虫剂之一，是世界上最受欢迎和使用最广泛的杀虫剂之一。我们的目标是分别从现成的糠醛和 D-甘露醇合成氧杂双环内酯 6 和五种新型拟除虫菊酯 8-12，并评估它们对四种具有经济重要性的昆虫物种的生物活性，即 A. obtectus、S. zeamais、A. monuste orseis 和 P. 美洲。描述了一种从糠醛中合成 6,6-二甲基-3-氧杂双环 [3.1.0] 己-2-一 (6) 的简洁而新颖的方法。异丙醇与呋喃-2(5H)-one 的光化学加成得到 4-(1'-羟基-1'-甲基乙基)四氢-呋喃-2-one (3)。醇 3 直接转化为 4-(1'-bromo-1' -甲基乙基)-四氢呋喃-2-一(5)，通过与PBr 3 和SiO 2 反应，产率为50％。最后一步通过 5 与叔丁醇钾以 40% 的产率环化进行。新型拟除虫菊酯 8-12 是由 (1S
• Process of producing cyclopropanecarboxylate compounds
  申请人：Sumitomo Chemical Company, Limited

  公开号：US06414181B1

  公开（公告）日：2002-07-02

  Provided are processes of producing a cyclopropanecarboxylate compound of Formula (I): The processes comprise reacting a cyclopropanecarbaldehyde compound of Formula (II): with a dicarboxylate compound of Formula (III): in the presence of at least one secondary amine from among piperidine, morpholine, pyrrolidine, diethylamine or N-methylethanolamine.

  提供了制备公式（I）的环丙基羧酸酯化合物的过程：该过程包括在至少一种二级胺的存在下，将公式（II）的环丙基羰基化合物与公式（III）的二羧酸酯化合物反应。所述二级胺可以是哌啶、吗啉、吡咯烷、二乙胺或N-甲基乙醇胺中的至少一种。
• Method for producing 2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate ester
  申请人：——

  公开号：US20010014755A1

  公开（公告）日：2001-08-16

  An ester compound, which is a production intermediate of a pyrethroid compound, given by formula 1 wherein R 1 represents C 1-6 alkyl group, etc., can be produced by allowing to react an aldehyde compound given by formula 2 wherein R 1 has the same meaning above, with a phosphorane compound given by formula 3 wherein R 2 represents a hydrogen atom, halogen atom or C 1-4 alkyl group, in an organic solvent, and obtaining a liquid distillate by heating the above reaction mixture with water in high yield.

  一种酯化合物，其为拟除虫菊酯化合物的生产中间体，由式1给出，其中R1代表C1-6烷基等，可以通过在有机溶剂中使式2给出的醛化合物与式3给出的膦烷化合物反应，并通过在水中加热上述反应混合物而获得液态馏分，高产率地制备。