3-isopropoxycarbonyl-2-methyl-2-propenylphosphonic acid diisopropyl ester | 50798-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-isopropoxycarbonyl-2-methyl-2-propenylphosphonic acid diisopropyl ester
• 英文别名: diisopropyl-3-isopropylcarbonyl-2-methyl-2-propenylphosphonate；triisopropyl (3-carboxy-2-methyl-2-propenyl)phosphonate；diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid；isopropyl 4-di(isopropoxy)phosphoryl-3-methylbut-2-enoate；di-isopropyl 3-isopropoxy carbonyl-2-methylprop-2-enyl-phosphonate；Diisopropyl 3-isopropoxycarbonyl-2-methyl-2-propenylphosphonate；propan-2-yl 4-di(propan-2-yloxy)phosphoryl-3-methylbut-2-enoate
• CAS: 50798-35-1
• 化学式: C₁₄H₂₇O₅P
• 分子量: 306.339
• InChiKey: YRPJERJNTCPIDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±35.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-isopropoxycarbonyl-2-methyl-2-propenylphosphonic acid diisopropyl ester 生成 isopropyl 11-mercapto-3,7,11-trimethyldodeca2,4-dienoate
  参考文献：
  名称：

  Novel products

  摘要：

  脂肪族二不饱和酯和酸及其衍生物，其中用巯基(硫醇)或烃硫基取代，用于控制昆虫。

  公开号：

  US03948996A1
• 作为产物：
  描述：

  三异丙基亚磷酸酯 、 isopropyl 4-bromo-3-methyl-2-butenoate 以75%的产率得到3-isopropoxycarbonyl-2-methyl-2-propenylphosphonic acid diisopropyl ester
  参考文献：
  名称：

  Stereochemistry of the Horner-Emmons reaction of 3-functionalized 2-methyl-2-propenylphosphonates with aliphatic aldehydes. 1. Effect of size of the alkoxy group attached to the phosphorus atom

  摘要：

  DOI：

  10.1007/bf00953422

文献信息

• Cyclic analogues of insect juvenile hormone
  作者：Karel Hejno、František Šorm

  DOI：10.1135/cccc19801734

  日期：——

  The preparation and the juvenilization effect of some derivatives of 3,7-dimethyl-9-(5-methyl-2-oxolanyl)-2,6-nonadenoic, 3,7-dimethyl-9-(5-methyl-2-oxolanyl)-2-nonenoic (methyl, ethyl and isopropyl ester, monomethyl and dimethylamide) and 3,7-dimethyl-9-(-methyl-2-oxolanyl)-2,4-nonadenoic acid (methyl, ethyl and isopropyl ester) have been described.

  已经描述了3,7-二甲基-9-(5-甲基-2-氧杂环戊基)-2,6-壬二酸、3,7-二甲基-9-(5-甲基-2-氧杂环戊基)-2-壬烯酸(甲基、乙基和异丙酯,单甲基和二甲基酰胺)以及3,7-二甲基-9-(-甲基-2-氧杂环戊基)-2,4-壬二酸(甲基、乙基和异丙酯)的制备和一些衍生物的幼态化效应。

• Odinokov, V. N.; Kukovinets, O. S.; Zainullin, R. A., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 8.1, p. 1289 - 1294
  作者：Odinokov, V. N.、Kukovinets, O. S.、Zainullin, R. A.、Kasradze, V. G.、Tolstikov, G. A.

  DOI：——

  日期：——
• Stereoselective synthesis of analogs of natural isoprenoids based on the reaction of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with aldehydes in ionic liquids and in an imidazolium salt—benzene system
  作者：S. G. Zlotin、G. V. Kryshtal、G. M. Zhdankina、P. A. Belyakov、E. P. Serebryakov

  DOI：10.1023/b:rucb.0000035653.43049.35

  日期：2004.3

  Condensation of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with a number of aldehydes under the Homer-Emmons reaction conditions in 1-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate and in 1-butyl-3-methylimidazolium bromide-benzene and 1-butyl-2,3-dimethylimidazolium hexafluorophosphate-benzene systems was studied. The E/Z-stereoisomer ratio of the olefination products for the reaction carried out in ionic liquids was 3 : 1, which corresponds to the values attained previously in the KOH-benzene-(Bu4NBr)-N-n (cat.) system. Quantum-chemical calculations were used to determine the averaged radii (r(0)) of the [(Bu4N)-N-n] and substituted imidazolium cations by means of the Gaussian 98 program package. The stereoselectivity of olefination in the KOH-PhH-phasetransfer catalyst system decreases with a decrease in the r(0) value for the catalyst cation. The possibility of recovery and reuse of ionic liquids is demonstrated.
• Synthesis of further 9-oxa and 10-oxa analogues of acyclic juvenoids
  作者：V. Jarolím、F. Šorm

  DOI：10.1135/cccc19751070

  日期：——
• On the stereochemistry of the Horner?Emmons reaction between 3-functionally substituted 2-methyl-2-propenylphosphonates and aliphatic aldehydes
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf00704196

  日期：1993.6

  The reaction of diethyl 3-ethoxycarbonyl-2-methyl-2-propenylphosphonate (1a) with 3-methylbutanal (2) in heterogeneous MOH (solid)-benzene systems in the presence of 5-10 mol.% of benzyltriethylammonium chloride (BTEAC) gives the reaction product (3) with a higher, for M = K, or lower, for M = Li, ratio of 2E,4E- and 2Z,4E-stereoisomers than that observed in the absence of BTEAC. Tetrabutylammonium bromide (TBAB) as a catalyst of the reaction 1a + 2 --> 3 in the system KOH (solid)-wet benzene leads to a higher [2E,4E-3]:[2Z,4E-3] ratio than BTEAC; this ratio grows from 44:56 without TBAB to 80:20 at 100 mol.96 of TBAB. In the latter case the stereochemical outcome of the reaction is similar to that obtained when tetrabutylammonium hydroxide in dry benzene is used as the deprotonating agent. The corresponding diisopropyl phosphonate (1b) and 3,7-dimethyloctanal (4a) interact in the system KOH (solid)-wet benzene-TBAB to give hydroprene (5) containing 88 % of the 2E,4E-isomer (5a) while in the case of 1 equiv. of [(n-Bu4)N]OH in dry benzene the content of 5a is 92 %. Diisopropyl 3-isopropoxycarbonyl-2-methyl-2-propenylphosphonate (1c) and 7-methoxy-3,7-dimethyloctanal (4b) under either of these conditions afford methoprene (6) containing 93 % of the 2E,4E-isomer.