dimethyl 2-but-3-enyl-2-prop-2-enylpropane-1,3-dioate | 112391-44-3

• 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: dimethyl 2-but-3-enyl-2-prop-2-enylpropane-1,3-dioate
• 英文别名: dimethyl 2-(3-butenyl)-2-(2-propenyl)malonate；4,4-di(methoxycarbonyl)-1,7-octadiene；dimethyl-4,4-dicarboxy-1,7-octadiene；4,4-dicarbomethoxy-1,7-octadiene；Dimethyl 2-but-3-enyl-2-prop-2-enylpropanedioate
• CAS: 112391-44-3
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: PUUDYFNPLYMOCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  260.2±40.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-but-3-enyl-2-prop-2-enylpropane-1,3-dioate 在 氢氧化钾 、 sodium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 2-(丙-2-烯基)己-5-烯酸
  参考文献：
  名称：

  Ramana; Reddy, K. Rajender; Nagarajan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 6, p. 534 - 540

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸二甲酯 在 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 dimethyl 2-but-3-enyl-2-prop-2-enylpropane-1,3-dioate
  参考文献：
  名称：

  Atkinson, Robert S.; Grimshire, Michael J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1135 - 1146

  摘要：

  DOI：

文献信息

• Tris(trimethylsilyl)silyl Radical Induced Bicyclization of 1,6-Dienes and 1,6-Enynes Providing 3,3-Bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes and 3-Silabicyclo[3.3.0]oct-1-enes
  作者：Katsukiyo Miura、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/bcsj.66.2348

  日期：1993.8

  Treatment of 1,6-dienes with tris(trimethylsilyl)silane in the presence of Et3B or α,α′-azobis(isobutyronitrile) afforded 3,3-bis(trimethylsilyl)-3-silabicyclo[3.3.0]octanes in addition to monocyclized cyclopentanes. Bicyclization of 1,6-enynes provided the corresponding 3-silabicyclo[3.3.0]oct-1-enes.

  在 Et3B 或 α,α′-偶氮二异丁腈存在下，用三(三甲基硅基)硅烷处理 1,6- 二烯，除了得到单环戊烷外，还得到了 3,3-双(三甲基硅基)-3-硅杂双环[3.3.0]辛烷。1,6-烯炔的双环化提供了相应的 3-硅杂双环[3.3.0]辛-1-烯。
• Coordinatively unsaturated ruthenium allenylidene complexes: highly effective, well defined catalysts for the ring-closure metathesis of α,ω-dienes and dienynes
  作者：Alois Fürstner、Monika Liebl、Anthony F. Hill、James D. E. T. Wilton-Ely

  DOI：10.1039/a900187e

  日期：——

  The well defined, conveniently accessible and coordinatively unsaturated allenylidene complexes [RuCl2(CC CPh2)(PCy3)2] and [Ru2Cl4(CCCPh2)(PCy3)(η-MeC6-H4Pri-4)] are highly effective catalysts for the ambient temperature ring-closure metathesis of α,ω-dienes and dienynes, illustrated by the facile and high yielding formation of variously functionalised 5, 6, 7, 8, 15, 16 and 18 membered mono- and bi-cyclic ring systems.

  定义明确、易于获得且配位不饱和的亚烯基配合物 [RuCl2(CC CPh2)(PCy3)2] 和 [Ru2Cl4(CCCPh2)(PCy3)(Î--MeC6-H4Pri-4)] 是δ、二烯烃和二炔烃的高效催化剂，可方便地高产形成各种官能化的 5、6、7、8、15、16 和 18 分子单环和双环系统。
• Radical translocation reactions of vinyl radicals: substituent effects on 1,5-hydrogen-transfer reactions
  作者：Dennis P. Curran、Wang Shen

  DOI：10.1021/ja00067a021

  日期：1993.7

  systematic study of the radical translocation (1,5-hydrogen-transfer) reactions of vinyl radicals is described. The effects of monoalkoxy, dialkoxy, monoalkylthio, dialkylthio, thiohemiketal, phenyl, allyl, carboxylate ester, nitrile, and tertiary, secondary, and primary alkyl substituents on the transferring C-H bond were studied. The protocol was first to generate vinyl radicals which were next translocated

  描述了乙烯基自由基的自由基易位（1,5-氢转移）反应的系统研究。研究了单烷氧基、二烷氧基、单烷硫基、二烷硫基、硫代半缩酮、苯基、烯丙基、羧酸酯、腈以及叔、仲、伯烷基取代基对转移CH键的影响。该协议首先产生乙烯基自由基，然后通过 1,5-氢原子转移过程转移到新的碳中心。易位后发生快速自由基环化。使用 Stork 的催化氢化锡法、标准的化学计量氢化锡法和注射泵法进行自由基反应，在标准条件下都给出了可比的结果
• Electroreductive Dicarboxylation of Unactivated Skipped Dienes with CO₂
  作者：Wei Zhang、Li‐Li Liao、Li Li、Yi Liu、Long‐Fei Dai、Guo‐Quan Sun、Chuan‐Kun Ran、Jian‐Heng Ye、Yu Lan、Da‐Gang Yu

  DOI：10.1002/anie.202301892

  日期：2023.6.5

  A powerful electrochemical protocol that enables the first dicarboxylation of unactivated skipped dienes with CO2 is reported. Various valuable tethered adipic acids are formed in moderate-to-good yields under mild conditions, showing great potential in synthetic, medicinal and polymer chemistry.

  报道了一种强大的电化学方案，该方案能够使未活化的跳过二烯与 CO 2进行首次双羧化。在温和条件下以中等到良好的产率形成各种有价值的系链己二酸，在合成、医药和高分子化学方面显示出巨大的潜力。
• Development, Synthetic Scope, and Mechanistic Studies of the Palladium-Catalyzed Cycloisomerization of Functionalized 1,6-Dienes in the Presence of Silane
  作者：Philip Kisanga、Ross A. Widenhoefer

  DOI：10.1021/ja001730+

  日期：2000.10.1

  A 1:1 mixture of the pi-allyl palladium complex (eta (3)-C3H5)Pd(CI)PCy3 Cia) and NaB[3,5-C6H3(CF3)(2)](4) in the presence of HSiEt3 catalyzed the cycloisomerization of diethyl diallylmalonate (2b) to form 4,4-dicarbomethoxy 1,2-dimethylcyclopentane (3b) in 98% yield with 98% isomeric purity. The procedure tolerated a range of functionality including esters, ketones, sulfones, protected alcohols, and substitution at the allylic and terminal olefinic carbon atoms. Cycloisomerization of 2b obeyed zero-order kinetics to >3 half-lives with initial formation of 1,1-dicarboethoxy-4-methyl-3-methylenecyclopentane (4b), followed by secondary isomerization to 3b. Deuterium labeling studies revealed that the conversion of 2b to 4b was accompanied by significant H/D exchange, consistent with an addition/elimination pathway coupled with facile H/D exchange of the Pd-H(D) intermediates with free silane.